Time To Go Back To Work Full-Time Again?

Google bike at Googleplex

Going back to work to take a break from fatherhood after two year and making extra income sounds like a good idea now! After all, there are less things to do during the pandemic. So you might as well find a job where you can work from home, work 2-hours a day, and still get paid full-time!

I recently visited my old friend Chris who works at Google. We first met on Craigslist when I put out an ad to hire someone to help build my blog network website back in 2009.

Chris took me on a two hour bike tour at what literally felt like a college campus with over 60 buildings. There's all you can eat food from every type of cuisine. There are tennis courts, a soccer field, a wave pool, and freshly squeezed orange juice when you're thirsty. Massages by appointment, daycare, and dry cleaning are all at your disposal.

You basically never need to leave the Googleplex, which is exactly what management wants. My time at Google reminded me about how much fun work could be.

In fact, I regularly see a woman who works at Google play pickleball for 2-3 hours during the weekday. Sign me up for a job that pays me to play!


After 24 years post college, I've been fortunate to experience working at a couple reputable firms full-time and pursue a dream of doing something entrepreneurial full-time as well.

But several things besides my visit to Google have been pushing me to take full-time work seriously again.

  • No matter how much you love someone, it's rather difficult spending 24/7 with your significant other every day, especially after at least one of you was out of the house for 12+ hours a day. Separation is very healthy for relationships. It allows you to recharge and re-appreciate what you have. I can't go to the park every day at 11am to go play tennis with my fellow tennis bums either. There needs to be a change of pace.
  • Despite going through a couple downturns in my career, I never really felt that much pain because I was never laid off. The bi-weekly paychecks kept coming in during the dotcom bust and the housing market collapse. Sure, my year-end bonuses got slaughtered, but my lifestyle didn't really change much because I always just invested all of my bonus anyway. As an entrepreneur, I'm hypersensitive to income fluctuations. Revenue can easily decline by 25% month over month as it recently did. There are so many exogenous variables that are outside of my control. If doom is around the corner, it would be nice to have some stability.
  • There's no more fear of regret. One of the main reasons why I left my day job in 2012 was because I didn't want to look back as an old man, filled with regret having never tried creating something on my own. A good 3.5 years have past surviving on my own and I'm proud of what I've accomplished. It's hard to build a livable income stream that can support four people in San Francisco. Now that the challenge is complete, I long for a new challenge.

The combination of consulting and working on your own business is pretty fantastic. You can make a healthy income while having a lot of freedom. However, there's a wanderlust feeling that grows when you don't feel you belong anywhere. I think we all naturally want to be part of some type of organization.

Related posts:

How Much Do I Have To Make As An Entrepreneur To Replicate My FT Job Income?

Bankers, Techies, Doctors: You'll Never Get Rich Working For Someone Else

A Day Job Is So Much Easier Than Entrepreneurship


Before making a big decision, I like to write out my thoughts. Here are some of the things I miss about working full-time from my old shop.

  1. The camaraderie of working towards a common mission. I love working together on a good team that is looking to compete against another company. It feels exactly like playing together on a softball, basketball, or football team. As an avid league tennis player, I love coming up with the lineups and talking strategy with my fellow teammates. Sitting out a match to make way for a better player is not a problem because the thrill of victory trumps everything else.
  2. The corporate card. As a frugal person who likes to hustle, it's awesome to be able to eat a free meal while developing client relationships. Because I love saving money, I made it a point to try and take as many clients out for lunch, dinner, and drinks as possible. The real reward was building one of the strongest west coast franchises on the street, which led to even more gains.
  3. The commiseration. Every day can't be a good day. Sometimes we lose out on a deal, fall in the rankings, or get fired by a client. Commiserating with colleagues about what could have been always felt pretty good because we were in it together.
  4. The boondoggles. Every decent company spends a lot of time and money on making sure their company culture is strong. Part of good company culture is having happy employees who get along with one another. I know Uber, for example, had a company-wide trip (5,000+ employees) to Vegas for four days. Talk about fun!
  5. The security. Getting a paycheck every two weeks felt amazing. It was easy to save one and spend the other to get to a 50% after-tax savings rate. I'm now purposefully paying myself in the middle of the month to replicate a bi-weekly paycheck cadence because I receive my rent checks at the beginning of the month. Unless you really screw up, it's hard to get fired.
  6. The benefits. I pay ~$1,460 a month for health insurance for two healthy people in their mid-30s. That's a ridiculous amount of money when it costs a tenth of that amount in some other developed countries. I miss the 401k match and annual company profit sharing, although most startups don't match. I also miss the continuing education training and tuition reimbursement program that paid for almost all of my Berkeley MBA. The short-term and long-term disability leave was also nice. Read your employee handbook everyone.
  7. The recognition. The most exciting time at the company was during promotion period. Everybody would eagerly wait to see who got on the CEO's promotion blast list. The flood of congratulation e-mails, pats on your back, and handshakes if you got promoted always felt really good. Getting recognized for a job well done is a fundamental necessity.
  8. The networking. Even though competition was fierce, it was always fun to go to networking events and mingle with competitors. Some would share secrets about shared clients. While others might want to poach you away for big bucks. As a relatively extroverted person, the networking events were always enjoyable.

Latest Statistics About Work

    •  58% of people work from home or 80 million people
    •  Based on a survey, 60% of the employees claimed they would prefer to continue working from home
    •  There is a 62% increase in remote workers' productivity
    •  Remote workers feel 60% less connected with their coworkers

Quiet quitting is also a big thing! So is not working if you get to work from home.

Due to the prevalence of working from home, people no longer need to strive for FIRE and early retirement. Why retire early when you have so much more work flexibility?


If you can find a reputable job that gives you the opportunity for growth, while giving you the freedom to pursue other passions outside of work, I dare say it could be an ideal situation. The trouble is finding that perfect company!

There's nothing better than starting your own website to own your brand online and earn extra income on the side. Why should LinkedIn, FB, and Twitter pop up when someone Google's your name?

With your own website you can connect with potentially millions of people online, sell a product, sell some else's product, make passive income and find a lot of new consulting and FT work opportunities. 

Start your own WordPress website with Bluehost today. You never know where the journey will take you!

Recommendation For Leaving A Job

If you want to leave a job you no longer enjoy, I negotiating a severance instead of quitting. If you negotiate a severance like I did back in 2012, you not only get a severance check, but potentially subsidized healthcare, deferred compensation, and worker training.

When you get laid off, you're also eligible for up to roughly 27 weeks of unemployment benefits. Having a financial runway is huge during your transition period.

Conversely, if you quit your job you get nothing. Check out the book How To Engineer Your Layoff: Make A Small Fortune By Saying Goodbye.

It's the only book that teaches you how to negotiate a severance. It was recently updated and expanded thanks to tremendous reader feedback and successful case studies.

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127 thoughts on “Time To Go Back To Work Full-Time Again?”

  1. Frederick Atwater

    Sam, that’s quite an honest answer.

    You have a financial industry background, so you might find this question interesting (or maybe not)…Have you considered learning how to use short options and delta balanced futures (long or short) to risk mitigate your exposure? Just curious.

    Fred Atwater

      1. The markets crashed almost 20 percent last week! The Feds 50 bps did not inspire the markets!

        Always be learning

  2. Hi! Long-time reader but I’ve never commented…until now ;) I feel compelled.

    I worked FT, quit my job, then freelanced for three years. I freelanced PT but some months earned more than I did at my FT job.

    After three years, I was ready to rejoin the workforce, and so I did (I work in finance, too). This was in July of this year. I can honestly say I’m already ready to be back at home freelancing, but I’m going to give it some more time. This post was a wake-up call that that is just how we as humans are – we are constantly looking for change and I honestly think that’s great! Whether you work for a company or work for yourself, doing basically the same thing day after day gets old.

    I read a quote the other day that resonates with this – Sh*t gets old, fast.

    I say take the job. It’s been fun having coworkers and the office camaraderie. Plus, if you get sick of it after a month, a year or 10 years, you can always quit :) That right there is the beauty in not needing to work for money.

    1. Howdy Sarah!

      Nice to hear from you. Very interesting insight about you going back in July and just three months later, you’re ready to go back home to freelancing.

      I do wonder if I will feel the exact same way. After this post was published, I decided to send out feelers… and boy, was the feedback IMENSE. Six firms responded, I gave a startup incubator pitch yesterday, and I have 6 back to back hours of interviews one day next week + dinner, and three meetings the day before.

      One thing I did do was reach out to personal finance 1X1 clients. That was very rewarding and fun to hear people really appreciate the help.

      Good luck with what you decide too! I’ll keep everybody posted for sure. It’s fun to write about the journey. Maybe that’s it.. I’m looking to experience something new, in order to write something new.


  3. People want the opposite of what they have. When you have a job, you want to quit and enjoy your freedom. When you quit your job and start your own business, you miss the financial stability and social aspects of your old life. Whatever you do, you feel like you’re missing out.

  4. Hey Sam-

    A few things jump out at me –

    It sounds like you don’t have kids – this would make it much more appealing to work because you don’t have to spend several hours a week taking care of them, etc. On the other hand, if you don’t have them and aren’t planning on having them, you need less money so could also be an argument for not working.

    Have you considered writing a book about how to become a successful blogger? Or on how to be a financial samurai? How about teaching personal finance and/or entrepreneurship in some capacity?

    I do think if you go to work in Tech, it will be a much more engaging and interesting time compared to Finance. In Tech, people are really passionate about solving problems and making great products, whereas in Finance, people just want to make money (obviously a generalization).

    You are in an interesting position to get a pretty good gig in the tech space, making the choice to go back to work a much easier one. The question is would you look at a start-up or a more established firm. A start-up is more interesting but probably would be much more demanding and you would probably find yourself working 60+ hours a week. In an established firm, you could still maintain a pretty solid work-life balance and find something you’re interested in. Obviously, there wouldn’t be a chance to get really rich like you would at a start-up.

    I think an interesting space would be at an established firm but working on a start-up project (think project Titan). You would have the resources of a huge firm, the benefits of a huge firm, and the independence/creativity of a start-up feel. Not exactly sure what capacity or project you would fit into, but those seem pretty interesting/unique to me.

    I am also not sure why you are set on a 3-year commitment. 3 years (as you mentioned) is a LONG time in tech. I would say a 2-year commitment seems more reasonable, and that is only if you like what you’re doing after the first year…If not, get out.

    I don’t know you so take this for what it’s worth – but you seem like a pretty competitive person and someone who likes to “prove” yourself to others. In our society, working can be a big part of that. If you get the right gig, you may get a lot of satisfaction out of helping to build a team/product while “proving your worth” to your immediate co-workers.

    The thing I personally don’t like about working at a company is that it is an “all or nothing” game. It would be great to be able to work either 3-4 days a week, or have a schedule where you work 4 weeks then take the 5th off..etc. Unfortunately, if you start working at a company, you are going to have to be “all-in”.

    Also consider if you value learning for the sake of it. Are you currently learning new things? Do you care to? There are several other ways to learn besides working at a company, but if you do go back to work, you will most likely develop new skills and learn more.

    I know a lot of people here have a goal to retire ASAP. My dad is 66 and still works even though he doesn’t need to and he simply says he doesn’t know what he would do all day if he didn’t have a job.

    I met a founder of a start-up who sold it and made millions when he was 30. He founded a new company right after the sale and has been working away at it for 2 years. I asked him why he cares to work so much when he is already so rich and his response was “being rich doesn’t matter. Being relevant does.”

    1. Interesting feedback from the rich founder. I can agree with that. And if anybody wants to FEEL relevant, writing online to a relatively large audience with great feedback such as yours is one of the best ways to go. I just got done with three personal finance 1X1 consulting calls this week, and it felt AMAZING to help different people with their different financial problems at different stages of their lives. Simply amazing.

      This site, and others, provides fantastic online stimulation. I’m seeking more offline stimulation.

      I really want to prove myself, to myself. Getting challenged is great, and it probably comes from the athletic side of me. Getting beat 6-0, 6-1 is embarrassing, but great, b/c it is a challenge.

      What are you up to?

      1. Living in NYC, working for a large tech company after leaving a bulge bracket bank, trying to figure out what I want to do with my life (-:

  5. I really sympathise with a lot of your thoughts and observations here Sam. Very similar to how I feel after almost a year of “Early Retirement”. I got very close to taking a full time job until my mate asked me “Do you think it will enhance your current lifestyle”? The answer to that was a resounding “No!” Incidentally I read that Google has a high staff turnover, average employee lasting about two years. Strange, if it’s as great as everyone makes out. Your probably have to swop your life for theirs, and no amount of free orange juice and bean bags makes that worthwhile.

    1. Hi Jim, after 3.5 years of doing whatever the heck I want, I do long for more structure. Come back to me next year or in two years w/ your thoughts on Early Retirement and see if your feelings/situation changes!

  6. Good article. If the idea appeals to you, why not? If you find out it doesn’t appeal after you give it a shot, at least you tried. Also, if you’re bored and want a different challenge, what about starting that family you’ve talked about?

    I personally enjoy blogs that delve more toward the personal esp in regard to raising well adjusted kids who aren’t spoiled although parents are FI.

  7. Didn’t get through all the comments so this might have been addressed, but why not try to build something bigger using your brand and resources that would require partners and staff? This would give you the human interaction with company dynamics but leave you firmly in the entrepreneurial driver seat. Bit more risk but could also be very lucrative and you’ve already got a head start with your finance background and self made businesses experience.

    1. I’ve got a laundry list of things I plan to build under the FS brand:

      * More books beyond severance negotiations and the Best of Financial Samurai e.g. real estate, investing, early retirement.

      * Building a product. I’m going to interview with an incubator today actually.

      * Going more public.

      But, I don’t like to manage a bunch of people b/c I find my expectations are too high of others. I don’t want to be disappointed. I also like the lifestyle business where I go at my own pace.

      How about you?

  8. I voted: No, it’s not worth losing 40+ hours a week of freedom. But based on what I’ve read from you, Sam, it sounds like you can’t go wrong here. You won’t be going back to work for the money, you’d be going back for the mental stimulation – no? If that’s the case, will this 40+ hour job take away from your other independent ventures? It hasn’t taken me long to figure out that time is our most precious resource, you gotta go with what will keep you interested, refreshed, and excited to wake up every morning.

    1. Yes, the camaraderie and challenge first. The money is a great benefit no doubt that will help smooth out earnings volatility as well.

      Even though I realize time gets more precious the older I get, I’ve already experimented with max work and no work with my time. I feel I’ve found a proper calibration.

  9. Lord Metroid

    If you want to go back to work, go back to work. You are financial independent and can do whatever you wish. When at work you do not need to fear being fired like the rest of us and can speak and act your mind freely. Worst case scenario is that you find out work isn’t all that jazzy you wished it was and quit to either work for someone else or work in your own enterprise once again. You got nothing to loose.

  10. I make over $500k a year working 20 hours a week, never travelling for business and taking 6-7 weeks of vacation each year. Its a nice balance and the wife and I still get along since I am not in her hair 24/7.

  11. What about looking for an opportunity to be a partner with a VC fund, or something along those lines? You’d probably have more autonomy over your schedule than as an employee, and with your combined background in finance and technology, it might be a good fit for you, and you’re in a position to take less compensation in exchange for more equity, which could be good. Just a thought as a regular reader of your blog.

    1. I think that’s a great idea BH. Being a VC is one of the cushiest jobs around. People pitch to you. You invest other people’s money. You make a cary, and sit back for the next 10 years! I’ll look into it more for sure. thx.

  12. FS, do what you feel. It is one thing to ‘decide’ to go back to work f/t, but my thought is that the real question is “what kind of job can you get, and for what compensation?” What kind of title, pay, duties are your a) aspiration; b) expected; and c) minimum? If you know those three combinations, you have your criteria. It would be great if you care to share them.

    SF seems to be a completely different animal for a lot of things financial, but from my own perspective the labor market is very tough to re-enter at a satisfactory point. The ‘three-year commitment’ is great, because I know for myself that the first time somebody is uncooperative or makes things personal that I will be out-the-door!:-)

    Another option, which I’m sure you have considered; can your DW/S.O. take a sabbatical while you return f/t, and you switch places for awhile? Maybe the stress you both feel is not so much based on ‘togetherness’ but on equity? Well, she must be quite special for you to have chosen her, and her input and thoughts on the decision you face will be quite valuable.

    One last thing noticed; you had discussed expanding your family, and a f/t return to a worklife would really impact your available time/energy/resources to dedicate. If it isn’t a priority, it is perfectly fine to defer or change your mind. Keeping good thoughts for you, as you work your way through the branches of this decision-tree!

    1. Hola JayCeezy,

      The DW doesn’t need to take a sabbatical because she no longer works a day job to take a sabbatical from. It’s just she and I 24/7, hence it would be nice to mix things up. I don’t think there will ever be true equity contribution in a relationship, and that’s not a problem. But I do believe there needs to be equity in effort.

      It’s weird, but I have no desire to be a head honcho at a big firm. I’m already the top dog at my own firm. Instead, I’d rather blend in. It feels warm, comfortable, and frankly, makes me a little giddy to assimilate.


  13. This is a great article Sam. It captures some of the ambivalence I feel about retiring early, even with substantial financial security. I haven’t really seen this type of discussion in the FIRE blogging community. The focus is typically on either extreme frugality or using side hustles to escape a job they truly hate.

    I particularly think that people underestimate the job security that comes from a variety of job attributes:

    1. Being a revenue generator
    2. Having detailed technical or organizational knowledge that allows you to get things done efficiently and breakthrough corporate red tape
    3. A history of proven performance
    4. A solid relationship with your boss and his/her peers

    If the company is growing at a respectable pace for the industry, there is some amount of inertia that allows even below-average performers to hold onto their jobs for many years. For above-average performers, this locks them into a very stable situation. As you say, only a massive screw-up (or maybe an acquisition) is potent enough to knock things off track.

    In a broad sense it’s very true that no job is safe, but for given situations I think the generalization doesn’t apply, based on my years as a consultant seeing the inner workings of dozens of companies.

      1. I have indeed, but once you have a kid the equation changes. Your future expense projections get turned upside down and OMYS starts looking like a feature, not a bug.

  14. Have you thought about other projects of your own that might take up more time and use your talents. You could probably expand your financial advising side hustle into a bigger operation. Might not give you all of the benefits, but it would also avoid a lot of the down sides.

    1. Good point. That is exactly what I did yesterday. I reached out to several people who filled out my personal finance consulting form, and I have a call with one this morning, and two more calls this week!

  15. Maryellen McDonald

    Absolutely, if that is what is in your heart to do then so be it especially if it’s good for your relationship. The financial aspects will be good for you but I have the impression it isn’t about the money. I am preparing to retire in another 2 – 3 years and I am excited about it. I believe I will probably find work for 2 – 3 days a week because it is what I want to do not what I have to do. Successful accomplishments that maintain your confidence, keep your brain flowing and activities that you can continue to learn from are all very good for you. It keeps your life balanced. I don’t believe it’s the money for you but something more personal. Of course the benefits are sweet but the personal rewards to will receive will make you happy and happiness in life is the goal.

    Good luck & enjoy. I am happy to hear you will continue with your writings as I do enjoy & learn from them. Thank you…..

    1. You’re going to love having the freedom to do what you want 24/7 in 2-3 years. It is also wise that you know you will probably want to work 2-3 days a week too. It’s hard not to, after a lifetime of work.

      There will, however, be a moment of sadness when the time comes. Becomes that is the point where you look back and realize that stage of your life is over. It’s now up to creating a new path!

      Related: What Does Retirement Feel Like? The Pros And Cons Of No Longer Working For A Living

  16. You sound bored with your life! You need new challenges and that does not come from going back to what you left behind. What happened to your product venture?

  17. Great post, Sam, and something I’d always wondered if you occasionally considered. I think you have to find your own way. You have options–that’s what FI gives you. I’m working full time (usually ~ 10 hours of non-stop, on-my-feet, immediate demands) so get exhausted. I’d like to work a few more years full time, and then, because I spent so much time going to college and vet school, work 2-3 days/week. I don’t want to lose that connection with animals and with the people who love them– I just can’t continue the pace indefinitely.

    Let us know– you are not only an inspiration, but fascinating to follow!

    1. 10 hours on your feet non-stop is A LOT! How do you do it? I get tired standing after just an hour, and need to plop down on my day bed when writing a post. I LOVE animals too! I’m thinking of being a part-time dog sitter. There are lots of new startups here that provide this service e.g. DoggieVacay.

      Thanks for sharing your thoughts and reading!

  18. The Universe just spent 13.8 billion years creating you. There’s nothing you can do to try to control it. Don’t try to have a single career. To have a “purpose”. To “figure out what you want to do”. Just do the best you can each day. If you don’t know what that means, you have to figure that out for yourself. If anybody tells you what it means, then they don’t know what it means. – James Altucher, The Rich Employee

    You might benefit from this book Sam. Good luck with your decision!

      1. I cashed out of an ESOP corporation about a year ago to pursue a higher calling with a non-profit cooperative. My work involves helping electric utilities balance their costs with the need to provide reliable power. Specifically, the reason why I go to work is because of the idea that in some way I hope my contributions are helping folks in rural America keep their lights on.

        Thanks for your continued efforts with the blog Sam. You have been an inspiration to me and my family. Whichever path you decide, I hope you are able to find peace in your restlessness. -Aaron

  19. Hi Sam, I am struggling with the same thoughts as yourself, but I voted “No don’t do it!” in your poll. I was down in London the other day considering a job offer that would see me back in paid employment. There were a lot of upsides, not least the money and security, but the friend I was staying with gave me this advice as he was heading out to his office, “Jim, if it doesn’t enhance your current lifestyle, don’t do it”. I really liked the idea he floated, that work should add value to how you’re living your life, not detract from it. On this basis, I decided to pass on that particular job. Maybe if it had been a 20 hour a week job as opposed to 40 I’d have grabbed it. I suspected, however, it would be (me being me) a 60 hour a week job. So no thanks!

    1. 20 hours a week would be amazing. I did 25/hours a week when I was consulting for Personal Capital. But have you ever wondered with the really wealth continue to work? I want people to think about that. I don’t think anybody has commented yet. Why work, when you don’t need to work? Anybody?

      1. Sam, Here’s why I work when I don’t need to.

        1- Most all of my friends have to work. “Nobody to play with during the day.

        2- To lazy, comfortable, or scared to make a change

        3- I got a real cool office I get to play on the internet during the day

        4- Keep some long time employees employed.

        5- My wife and I need a little break from each other some days.

        6- My daughter is still in school. “Hard to take a lot of time off when you have school, sports, and a social life of a 16 year old girl to attend to.

        7- Money. Why not another million?

        Thanks, Bill

  20. Sam, you are definitely not a disappointment. In fact you’ve gained even more credibility (IMHO) by publishing this article. Your honest assessments and unbiased articles are what truly separates you from other writers in this space

    Before you make your decision, I think these questions may help you assess your situation..

    Will you learn anything new by working for this fintech company?
    Which of the benefits that you’ve mentioned do you consider most important?
    What other paths/options do you have that might provide you those same benefits?

    1. Thanks Allan.

      These are good questions to ask oneself. I’ve learned as much as I can in the digital wealth management / roboadvisor space (Wealthfront, FutureAdvisor, Personal Capital, Motif Investing). I’d like to explore the consumer loan / payment space, which is taking in a lion’s share of capital at the moment.

      I’ve got two other options I’m considering: working at a public internet company in a different capacity, or going all-in with a product I want to build via an incubator.

  21. Sam,
    You should’ve saved this one for April 1st; that’s normally when bloggers publish jokes like this one.

    You are crazy, man! All your reasons are totally legitimate, and I can sympathize, but as some other commenters have said, try to recall the 100+ reasons you left the workforce.

    I’m glad to see that you’re seeking feedback on the topic, so that at least means you’re giving it considerable thought. But, think about it like this…You are in your mid-30’s, and quite wealthy. You are in a place that 99.99% of people will never be. You can do (almost literally) ANYTHING you could ever want to do…and you want to go back to work for somebody else?

    I get your reasons. I really do. However, consider some alternatives. Take an activist equity stake in an emerging company. Continue building FS and perhaps expanding this network considerably. Buy a villa in Ecuador. Become a professor, teaching all these lessons in an environment completely void of rational financial thought. Sail around the world.

    I’m totally shooting from the hip, here. But, understand that “jobs” will always be available to you (and most of us). For a man of your drive, savvy, and resources, you could be destined for world-changing kinda stuff.

    My two cents.


    1. Haha, awesome comment Eric! Much appreciated! I do have an April Fools Day post.. but I won’t be publishing it then!

      There were only two, not 100 reasons why I left my old job:

      1) It was no longer fun working in finance after 13 years

      2) There was no more correlation with performance and reward.

      The ultimate correlation with performance and reward is being an entrepreneur! And my biggest fear leaving a job was that I would be a fraud, that my efforts wouldn’t amount to jack shit. That if I didn’t have my firm, I would never be able to earn such an income.

      After 3.5 years, I’ve slayed that unknown, that fear. There is no more fear of regret because I didn’t try. I tried it ALL. I walked to the end of the rainbow to see what was there. And what was there was the same as it always was. A happy spot that lures people to new challenges.

  22. After 2 years leaving my job as an IT Admin and experimented with selling products on eBay, creating websites etc. I worked again as an IT Admin but now as an freelancer. And I realized that it is the most fun for me personally. What I also found out is, that I didn’t like my job at the first place because it was the wrong environment / company for me. That was the reason I did not have fun. So I’m very happy to have given it a try. Otherwise I never had found out this. After two finished projects as an freelancer I can say one project was very good and I loved to work there. All was right, from the colleagues to the meals and to the work ethic there. In the second project it was a mess. The company saved on everything possible, from the work environment to the kitchen. And it was no fun working there. So, if you want choose a job again for 3 years I think choose it wisely. If you find out soon the company is not good, it is better to leave soon as possible. That was when I realized that I never would go back as an employee. As an freelancer I moved on after 6 month. So I think it’s very important to decide for what company you want to commit for 3 years.

  23. If/when you become an employee again, how much of your contribution will you be paid for? How much will your employer make off you?

      1. I guess my point is that you have the skills, experience, and resources to start/buy your own business, build the culture you want, and get paid all the profit.

  24. I’ve been following your blog for awhile now, and from what I know about you I don’t think there’s a wrong move you can make. The beauty of being financially free is that you can go back to work if you want to, for a long as you want to, and when things don’t suit you anymore, you can walk away…

    Hell, that option alone is worth more than money itself. I work as a software developer and have been saving 50%+ of my income for the last few years with the hopes of achieving that kind of freedom. In fact, I often fantasize about taking on random jobs later in life just to try them out (janitor, retail, customer service, sales). I never did those kind of jobs growing up. I basically went from HS/College/Programmer… I would love the opportunity to experience different walks of life — to walk a day in someone Else’s shoes so to speak — but with the freedom that I wouldn’t be stuck in any single position. Walking away from my ‘cushiony’
    job right now wouldn’t be smart, but you seem to be a position to do just that and not lose much from the experience… I say go for it!

    my 2cents.

    1. Nice job saving 50% of your income on a consistent basis! You will reap the rewards of financial independence sooner than you realize!

      You don’t have to fantasize about taking a random job later in life just to try them out. You can drive for Uber and immediately feel what it’s like to work a lower hourly wage and deal with difficult customers. You can try TaskRabbit too. Get yourself beat up by the world to appreciate more of what you have!

      I think a lot about commitment. If I am to go back, I want to commit to at least 3 years. If it was only for 6 months, I would care much less about the decision.

  25. Sam great post. I wonder does it have to be either or? Given the nature of work today perhaps there is an arrangement where you can work for a company but still have a degree of freedom. There are many companies that allow employees to work remotely part of the time and perhaps an arrangement like this would work. I’ve worked solo since the late 1990s (most of the time from home) and wouldn’t have it any other way. I briefly shared an office and hated it. But that’s just me. I’d consider a real job under the right circumstances but frankly I don’t think I’m suited to go back to a strict be in the office 10-12 hours per day routine. I often work longer than that here but’s that my choice. Just my 1.5 cents worth.

  26. I love that you’re willing to openly consider an option like this. Retiring from full-time work seems to be the ultimate, holy grail, end goal for most people, where life will just be bliss forever afterwards, but we all change over time. I think most of us overestimate how much we just KNOW what will make us happy for the rest of our lives.

    Despite that, I still crave the ability to leave full time work like most others who have experienced nothing else, but I know I’d miss so many things about it. The best days, when I come home so happy from work, are usually after having meaningful interactions with other people, when I feel I’ve had an impact or just been helpful. That in-person praise or feedback for a job well done is a great feeling too.

    There are obviously no universal answers with this stuff, even though some of us sometimes act like there are – just keep doing what resonates most with you now that you have greater power to choose.

    1. I hope people take this post as a realization that their jobs might actually be quite terrific, and to NOT take their FT jobs for granted.

      I’m giving folks the real-time honest truth about how I feel after doing both FT.

    2. Mysticaltyger

      Jason, that comment about humans overestimating their ability to know what will make them happy is VERY true. Psychologists who study happiness have found this to be true in their research over and over again.

  27. Sam,

    I am one of the lucky ones that has found a job that allows me both the opportunity for structured growth of employment and the freedom to pursue outside entrepreneurial opportunities. My situation is ideal and unique, and even a bit unique for others in my industry.

    I am a 31 year old physician now 1 year out of residency, who works 70% of full time (about 12-13 days per month). I work in an speciality that only requires me to be accountable on the days I work. Therefore, of 17-18 days I am not working, I can fully devote to the hustle and grind of developing passive income streams.

    The days I work as a doc are incredibly rewarding as it allows me to critically think through complex medical issues, develop my skills, get social interaction from my staff and patients, aid people in times of vulnerability and generally feel accomplished for the work I’ve put in at the end of the day. Additionally, I get full benefits including health, dental, vision, 401k match, profit sharing, vacation, continuing medication, education funds, etc.

    Part of the reason I can get away with this is that it is a fairly high paying job, even for only working part time. I (like you did) save away 50% of my income and use all my bonus money to funnel into investing.

    Once my road is financial independence is solid, I would like to eventually drop to 50% full time (I can still retain full time benefits). This would mainly be for the enjoyment of the job and benefits, and not so much the salary. This may be the perfect balance of the advantages of employment and the freedom of being an entrepreneur.

    One of the best pieces of advice that I have gotten is “Choose Both”. Specifically, it iterates that when faced with two seemingly contradictory possibilities, it is up to us to think creatively and find a solution that allows both situations to coexist to our advantage. Maybe for you there is a choose both solution.

    Dr. Tin

    1. Congrats on making it out of residency! I remember being very excited my first 10 years of work after college, and I have to imagine the excitement for you is even more after starting to make real money at 30+.

      I say cherish is for as long as possible, while doing something you also love on the side. I hope your interest in being a doctor never fades, and the government stops squeezing the field.

      Unfortunately, I’ve noticed everything gets a little boring after a while.

      If you can do a 50/50 balance, I think that would be awesome doc!

  28. Sounds like you’re a strong extrovert since a lot of the things you miss about the corporate world involves other people. Specifically, I have you pegged as an ENTJ, only 2% of the population, the ‘executive/CEO/visionary’ type. If you don’t already know your Myers-Briggs type, here’s the free link:

    Most of the Fortune 500 companies use this test to determine what positions people are most suited for. I find it highly accurate, scarily so, since I’ve found out more about myself in the past 3 yrs (when I discovered it) than the rest of my life combined. If I knew my personality type when I was 18, I’m pretty sure I would not be in the career field I am in, nor would I be married to my spouse.

    Anyway, I think a full-time corporate job suits you since you derive so much energy from other people. And being an ENTJ, you are wired to achieve new goals and plan for the future. So to answer your question, yes, if I were you, I would go back full-time. However, if I were me, a strong introvert, I would never go back, since I dislike most people and become drained by too much social interaction. I am happy to go a week without talking to anyone. :)

    I’m a total Myers Briggs junkie and can never find anyone else who is interested (and knowledgable) enough to have deep, meaningful conversations. If you find this topic interesting, I would love to hear your thoughts (at least let me know if I’m right about you being an ENTJ) and perhaps a blog post dedicated to it!

        1. Mysticaltyger

          That comment was hilarious!!! I’m an INTJ so I can relate to what you’ve been saying, Sara.

          1. Thanks Mysticaltyger! I think you probably figured out that I am also an INTJ. We INTJs are so misunderstood. And considering the fact that I don’t know any fellow INTJs in real life (I would have to talk to 100 people to maybe find 1, and what INTJ is going to talk to 100 new people?!), I find that most of my wit and humour is wasted on the general population. Thank goodness my closest friend is an INFJ who gets my humour enough that I can overlook most of her irrational tendencies. :p Anyway, most Ns find that I spew out funny comments often, whereas S’ tend to have blank looks on their faces while my insights fly over their heads. Therefore, if I meet a person at a party who thinks I’m ‘no fun’, then I know they are boring and dim-witted and probably an S. But I have enough acquired social skills to never be rude or offensive (think Dexter), so I will smile and nod politely while planning my escape.

            Since most of my family members are S’, including my husband, I love him dearly, but I have to resort to my INFJ friend or cyberspace to get my fix of wit.

            I really can’t understand why people don’t actively use their MB type to improve themselves and their relationships with others. My relationship with my ESTJ husband has improved so much ever since I found out about our respective strengths and weaknesses.

            Do you have a blog? Would love to read it. If not, would love to read more comments from you!

            I really can’t understand why people don’t actively use their MB type to improve themselves and their relationships with others.

            1. I’m clearly not qualified or informed enough about this topic to make any claims, but I’m going to anyway.

              Answering those questions as honestly as I could during the test, I can’t help but feel that many of our tendencies or likes could easily be developed and changed with a bit of work and time.

              I think our minds are way more malleable than we give ourselves credit for. I remember being pretty extroverted as a child, but as I matured I ended up doing way more introverted type activities which changed me quite a bit, but that’s not to say I couldn’t go back to being a social butterfly if I worked on it and pushed myself.

              The test and topic is fascinating, but I’m not sure I’d put too much stock in it or set any strict limitations on career choices because of it.

              For whatever it is worth I’m an INTP, but I can’t help but feel that I could easily evolve to be another ‘type’…

    1. Nope, looks like you are wrong. The test says I am ENFJ. What do you think about that? This is their description, which sounds like a horoscope position to make people who are XYZ feel OK about their description!

      Extraverted iNtuitive Feeling Judging
      by Joe Butt
      ENFJs are the benevolent ‘pedagogues’ of humanity. They have tremendous charisma by which many are drawn into their nurturant tutelage and/or grand schemes. Many ENFJs have tremendous power to manipulate others with their phenomenal interpersonal skills and unique salesmanship. But it’s usually not meant as manipulation — ENFJs generally believe in their dreams, and see themselves as helpers and enablers, which they usually are.

      ENFJs are global learners. They see the big picture. The ENFJs focus is expansive. Some can juggle an amazing number of responsibilities or projects simultaneously. Many ENFJs have tremendous entrepreneurial ability.

      ENFJs are, by definition, Js, with whom we associate organization and decisiveness. But they don’t resemble the SJs or even the NTJs in organization of the environment nor occasional recalcitrance. ENFJs are organized in the arena of interpersonal affairs. Their offices may or may not be cluttered, but their conclusions (reached through feelings) about people and motives are drawn much more quickly and are more resilient than those of their NFP counterparts.

      ENFJs know and appreciate people. Like most NFs, (and Feelers in general), they are apt to neglect themselves and their own needs for the needs of others. They have thinner psychological boundaries than most, and are at risk for being hurt or even abused by less sensitive people. ENFJs often take on more of the burdens of others than they can bear.

      TRADEMARK: “The first shall be last”
      This refers to the open-door policy of ENFJs.One ENFJ colleague always welcomes me into his office regardless of his own circumstances. If another person comes to the door, he allows them to interrupt our conversation with their need. While discussing that need, the phone rings and he stops to answer it. Others drop in with a ‘quick question.’ I finally get up, go to my office and use the call waiting feature on the telephone. When he hangs up, I have his undivided attention!

      (ENFJ stands for Extravert, iNtuitive, Feeling, Judging and represents individual’s preferences in four dimensions characterising personality type, according to Jung’s and Briggs Myers’ theories of personality type.)

      1. Doh! ENFJ was my second guess! I rationalized that you make decisions based more on logic (T) than feelings (F), however, in hind sight, I can see that you care a great deal about people and their feelings, which is an F trait. The letters fall on a spectrum, rarely is anyone 100%T or 100%F. I actually think you are close to the middle of the T/F spectrum but tested a tad more on the F side. Did you get %s for your letters?

        In response to WinWin: it is true that our answers can change over time as we grow and many people cannot decide nor tie themselves down to a particular answer, so that when they take the test multiple times they end up with multiple types. ENFPs get the most varied results of all types, which is a clue in and of itself to their type. One piece of advice for taking the test is to answer as if you are your 12 year old self, before society changes how we would answer the questions based on what’s ‘good/bad’. Even the most spontaneous, go-with-flow kid has to learn to be punctual for school and work, so of course they become less P and more J over time. However, I believe that we only move along the spectrum within a 15% range, so nature is still the dominant force. But someone who starts off near the middle can easily test as one or the other depending on their mood that day. I agree that you don’t want to put strict limitations on career choices based on this (it’s good to explore first hand), but in my opinion it is a guideline helpful in achieving happiness and fulfillment. I spent most of my life trying to achieve my parent’s goals, but now I am achieving my own because I finally know myself enough to know what my goals are!

        Sam, based on this summary, do you feel you have traits of both ENFJ/ENTJ?

        Maybe what you read seemed a bit horoscope-y, perhaps this hits the mark more accurately? https://www.personalitypage.com/html/ENFJ_rel.html and
        I assure you, they are not all the same nor one size fits all, just read your opposite (ISTP) and you’ll see.

        Finally, here’s a fun chart on your Harry Potter and Star Wars character.
        So are you more Dumbledore or James Potter? I am always the ‘bad guy’ and I’ve come to like it. If you’re not a fan of either of those, then surely you must watch Game of Thrones! https://personalityclub.com/blog/game-of-thrones-personality-chart/

        1. I definitely think I have all those traits of ENTJ. Maybe I was ENTJ when I was still working. But now I like to follow my feelings more than logic. I believe everything is rational/logical by default.. and then go with how I feel about the situation.

          If it feels right based on logic, I’ll do it.

          I didn’t record the percentages. I just remember 44% for E, and maybe 12% for J.

          1. Ok, then you’re an ENXJ. A hybrid of ENTJ/ENFJ depending on the situation. Those are 2 of the types that I admire most, no wonder I enjoy reading your blog! They are also 2 of the most successful types. By the way, Oprah is an ENFJ, who wouldn’t want to be her friend.

        2. One more thing WinWin, I think the ideal type is to be almost 50/50 on each letter. That way you get the strengths of all traits. I would never have chosen to be born an INTJ. It is much easier to be say an ESFP (my opposite) in our society. I can definitely work at being more extroverted. At one point I forced myself to take a customer service job to improve my communication skills. I think I went from an 80% Introvert to a 65% Introvert. Ha. But being highly extroverted is not natural to me at all. I can do it for 3 hours maybe, but working a customer service job every day for 10 years would annihilate me. So now I focus on being the best version of an INTJ that I can be, I try to improve my weaknesses and focus on my strengths, namely innovating, analyzing and strategizing.

          Many people match 2-3 types. So maybe you can read a brief summary of all 16 and narrow down the ones you may be. As a possible INTP, you tend to like logic and theoretical possibilities, and you are very intellectually curious, so this should be right up your alley!

  29. I missed two things about working. The first was the social aspect, there’s something fun about working together on a common mission. It can be hard work, it can be stressful, but that all adds to the feeling of joy after a job well done.

    The second was the work itself. The work I do now isn’t as hard in terms of complexity, which I miss, but it’s still hard because now I’m dealing more with people and less with solving problems on a day to day basis.

    And sometimes it really is easier when someone else tells you what to do. :)

    1. Me too. I’m not sure people realize how tiring it can be always being your own CEO. There are so many decisions to make at once for survival and growth. It would be a great balance to have a more focused role at a firm, while still being able to do your own creative thing outside of work.

      I’ve resisted for years to make my online endeavors more of a business, b/c I don’t want this site to ever feel like a chore.

  30. Hi Sam, I had to weigh in. You’re lucky to have the choice. Although, I certainly wouldn’t be the one to advise you. I think you should do whatever you want. Most decisions can be changed and if you want to work full time again, why not? Just ask yourself what you would be giving up if you jumped back into the 9 to 5?
    Good luck!

  31. I have been reading your site for many months now. I have to say that your latest article left me beyond disappointed in everything you have been writing about. I get it, people need to work and provide for their families. They also need to contribute to the well being of the entire country (although it seems like more and more is being “taken” from the productive people an given to the non-workers)

    But this constant pull to always want to work more and make money just seems to be a no win situation. Is there no way to find happiness and be satisfied with your life without having your nose to the grindstone all the time? The upside to jobs you are talking about rarely exist.

    Have you ever sat with a loved one who is elderly and they pass on to the next life in front of you? It is so final and most would say that they would have wished to have the opportunity to enjoy more life and experience things rather than working themselves to death most of their life. Most end up only living a few years after retirement.

    We do all this silly retirement planning thinking we are living to 85-90 or beyond but let me tell you, most years past 70 or 75 are filled with aches and pains and not much quality of life for the majority of people.

    ENJOY what you have, be satisfied with your $175k or whatever you have coming in and live life to the fullest if you are able, think about all the people who don’t have the option.

    1. I realize I am a disappointment to many people. But that doesn’t stop me from trying to be better and work through the feelings and problems I have. Life has a fun way of always challenging me to find meaning.

      Yes, I have had two living beings I cared about basically die in my arms. It’s a very sad situation which had made me want to retire early in order to spend more time with family.

      I had a really fun time spending three months putting together The Best Of Financial Samurai, a 180 page ebook where 100% of proceeds go to an organization that helps keep inner city kids off the streets. I’d love your support if you’d like to purchase. Here it is: https://www.financialsamurai.com/how-to-make-money-quitting-your-job-2/the-best-of-financial-samurai-book/

      I’d love to know your story. How long have you been retired from work and do you wish you retired earlier? How old were you when you left the work force? Was there some deep regret you faced?

      What are some of the things I can do to help you more?


      1. I have not fully retired yet. I’m 53 and I’m probably in a bad place since I have lost both my parents in the last two years. I struggle like anyone else, I don’t have children but you always want to sit there and ask yourself, do I have enough? I have close to $3M put away including a piece of real estate.

        I crunch numbers all day long trying to determine if I have enough and reading your site gives me inspiration to think of selling out of my company I own. (of course now that I’m ready no one can afford to buy me out and my business partner lives paycheck to paycheck…lol)

        I guess if you get the dream position you are hoping for (which in my opinion doesn’t exist on all fronts) go for it, but remember, your an entrepreneur now and the first time someone above you with less capability or sense tells you to do something, it will bother you. I could never work for anyone again.

        My father was asking about his small investments 3 days before he died, think about that, worried about money 72hrs before you leave this life. So sad. I think you have more than most people right now, your young, travel the world, live in a beautiful city and own every minute of your life.

        Just remember one thing, there are many ways to contribute to the world and it doesn’t have to be about working and making more money. They say life should be lived backwards starting old and getting younger each day because of all the experience you have gained, do you really want to be working during those years?

  32. I had a very cool job for 10 years (doing radio shows) and it meant spending 3-4 hours/day in the studio and that’s it. I would NEVER get back to a ‘normal’ job, since it would mean I have to give up my own time. What I love the most, when it comes to running my very small home based business, is that I can spend the time as I want. not gonna give it up :)

  33. Go for it! You like working and the office environment might be a nice change of pace. I hope you find the perfect opportunity, though. I wouldn’t want to work for Google. It sounds like work is all consuming there. Maybe you can get an executive position in one of those financial tech start-ups. You are an expert in this field.
    Best of luck!

    1. Thanks Joe. Yes, on the flip side, I know a lot of people who have quit Google or couldn’t stand the bureaucracy and all consuming culture there. With 40,000+ people, there are bound to be unhappy campers.

  34. Wanderingfoodie_95

    I recently found your site, and am digging your post especially this one. I work in accounting/finance, and previously worked as a consultant for a mid-tier cpa firm and then got recruited by a p/e firm to help take a company public.
    I wish, however, I had found you and your book sooner! The IPO plans fizzled out, and got laid off (although with a generous severance). When looking for another job, I decided that instead of holding out for the highest bidder. That I would try to find something fun and not work for another a-hole. I eventually won the job lottery and am now working for very popular and well respected brewery in northern California. The point of all this rambling is that I totally agree with you points on working. While I could retire (if I moved to a cheaper part of the country), I am having too much of a good time and I feel like my contributions are making a difference. I working in a growing company and industry, with great people – did I mention the free beer!
    Too clarify, I landed this job while winding down my previous work. I have never been without work since I was about eleven.

    1. So long as you got a generous severance, and were happy with the package, don’t sweat missing out on my book! But, I guess you might have been able to get a larger severance.

      Does the waistline grow with all the free beer? :)

  35. Dominic @ Gen Y Finance Guy

    Looking forward to see what you end up doing. Would you go back into Finance?

    What are the requirements you are looking for?

  36. At Google there’s a very good possibility of being able to work 80% time. You get 80% of the pay, but 100% of many benefits such as health insurance. It’s even possible to work 60%, but I don’t personally know anyone that does that. We will definitely consider working 80% after we start having children.

    1. I probably would have taken the 80% time work/pay at my old finance shop if they offered.

      Having one weekday off a week to do your own thing would probably be pretty awesome for many people!

      1. Yes! Great for parents, and there are also long-time Googlers who don’t need to work for money anymore that do 80% as well. In my ideal world both my husband and I will each go 80% and take a different weekday off each week. We’ll see if he goes for it. I’m pretty sure we’ll at least take 90 days of unpaid leave in addition to maternity/paternity leave.

  37. Once you’ve truly hit FI, which I think you are very close to your 200k passive income target, work is less about the money than it is about just getting out of the house and feeling a sense of purpose.

    Some of us just aren’t wired to kick back for long periods of time. Some are. Both are okay, but it seems you’ve resigned to feel that you are not one of those people who can just relax.

    Might be a fun experience to work at one of the big tech companies, or even a smaller different company one if the position is right for you. No shame in enjoying work!

    1. Ravi,

      I honestly think I reached FI about three years ago. I’ve just created targets in order to keep motivation alive. Progress is happiness. If you’re coasting, you’re going downhill.

      Remind me what you’re up to nowadays?


  38. Love the blog and this post in particular.

    It’s interesting. I think most hard working people would dream to scratch the itch of building something of their own while chasing the unicorn of entrepreneurial wealth. You’ve done it better than most will even come close to, it sounds.

    I’ve somewhat run the gamut from startup to currently working at a tech giant. Both have very appealing attributes. Right now, I’m loving the security, social aspects, strong pay days, and a ton of other benefits you’ve mentioned in the post.

    That said, I often wrestle with the option of going to the right start up to get back to the “build your own success” environment. While not a perfect comparison, its what I am relating to right now. I’m on the young side and will probably build my financial nut to empower me to leave in a couple years if I build or find the right opportunity.

    Grass is always greener, but it sounds like you’ve checked all the right boxes and obviously you’ll do your homework to find a perfect fit. The important part will be to find something that allows you to continue to pursue everything you love about entrepreneurship while adding the benefits of a full time gig. I’d say go for it! The beauty of it is that you have plenty of options to revert back to what is best for you.

    Sidenote- Would you turn FT at Personal Capital? Love the service and company wish they had more east coast offices!

    1. Howdy James,

      That’s great you’ve been able to experience the startup and the tech giant. It definitely does feel different, and I think more rewarding to be in the “build your own success” environment don’t you think? Although the Googleplex was amazing, I wonder how often people who work there feel that their talents aren’t being 100% utilized. They can pick from the best and brightest.

      I’m glad you like Personal Capital! What’s not to like about using a financial tool that’s free and can help you better your finances right? Because I’ve had experience consulting with them for two years, and am currently an affiliate partner, I think it would be wiser to look into a different area of the fintech space. The consumer loan space seems to be where there is the most demand as evidenced by the $1 billion raise by SoFi.

      The goal is to find a company that is going places that has a need for my skillset.


  39. Ali @ Anything You Want

    I spent 2 months this summer not working, and going back to work after that hiatus definitely reminded me why I like working a traditional job. For me, the security of knowing that I’ll get a paycheck every week is the most important thing. I also really enjoy the sense of purpose of going into an office every day, working with others and feeling like I’m contributing to something larger than myself.

  40. Wow! Reading this from the viewpoint of still “working for the man”, I’d much rather be on the other side and happily be doing something on my own.

    Still though, I know some of the feelings of looking back on a company and reminiscing. I couldn’t wait to get away from my last company and move on, but then looking back there were moments that I missed like the camaraderie and having something exciting to be part of (especially when the CEO was charismatic to follow).

    You always have the option of going back, but I’m guessing once you get there, you might change your mind. Ha!

      1. True! But then I get to decide what holds meaning for me instead of only having the option of 1 amazing day a week. I think that’d be a great dilemma to have. :-D I’ll cross that bridge when I get there.

  41. I can relate to a lot of the things you bring up, esp. what you said about camaraderie and stability of a regular paycheck. I met up with a bunch of my old colleagues recently, some I hadn’t seen in over seven years, and it brought back a lot of fun memories of teamwork and working towards similar goals. If I was still working for that firm, I don’t think I would have felt the same level of camaraderie seeing past colleagues though. I think some jealously would be thrown in there as well because they were able to get out and do something more fulfilling.

    I think it’s natural to seek new challenges whether you find them in your business or in a new job. You’re fortunate to have the options to be selective in whatever offers come across your plate. Listen to your gut and if you have enough uncertainty about a particular role, you shouldn’t feel bad to wait for something better. Finding the ideal fit of colleagues, an admirable boss, meaningful work, reasonable hours, compensation and commuting can take time but it can also be quite exciting. Whatever you end up deciding to do, I think you’ll make the most of it and will excel!

    1. Thanks Sydney. It’s hard to be the boss all the time. It would be nice to be the boss outside of work, and an employee who doesn’t have to make all the decisions all the time at work.

  42. I suspect most jobs are like childbirth Sam, you remember the baby and not the necessarily the pain it took to bring it into the world. It’s hard not to think one’s freedom is more important with lots of interesting solo or joint ventures sprinkled in than going back to someone owning your time. Of course I’m looking at it from the POV of working 16+ years without a break. I’m envious you have the choice!


    1. 16 years straight is impressive Chris! Especially if it’s in the same industry. I wanted to last 18 years straight to age 40 and hang up my boots, but I couldn’t take it any more. I also didn’t anticipate discovering the online media world.

      Hopefully this article helps give FT working folks a renewed appreciation for work!

  43. IMO, having read your blog now for a couple of years, I think you have more left in the tank should go back to work for another stint. You’ve never really “quit” you just shifted to a much more flexible schedule that is 100% on your terms which is awesome. Your first retirement coincided with total crap times in your industry…which it was in my industry as well, but I stuck through it mostly because retiring early wasn’t on the immediate radar even though I had the means. Having lived through a huge rebound it was time to cash out and relax a bit, in my first 8 months it has not occurred to me to go back to work…but I realize that at some point it probably will be on my radar as well, but I’ll choose something really fun! I’d say your experiences over the last few years building your business will be invaluable and allow you to provide insight to your next gig few will have. Choose wisely but go into it with an exit strategy as well then go onto retirement #2!

    1. It’s nice that you’ve been reading and commenting for a couple years now!

      I would say that my first departure came two to three years after the worst time (2009-2010) since I left in 1H2012. I could have hung on for another one or two more years, but the correlation with performance and reward in finance completely went off tracks.

      It really feels like momentum in the economy, real estate, and stock market has all slowed down. I thought the momentum in the tech private market slowed down until SoFi announced their $1 billion fund raise from Softbank. Perhaps that’s it….. maybe because I feel we’ve only got 2-3 more years of crazy private company momentum, that I know there’s a backstop. When you know there’s a backstop, you can do anything!

      1. Time flies doesn’t it! I honestly wouldn’t worry about the momentum in private tech…yes there will be dips here and there but the trend is always upwards. There will always be a need for the high level performers and a new idea or product to focus on…actually the bad/slow times is when you can really make hay imo. I’m a few years older than you and I’m personally was not ready as early as you, working was still fun. Only question I have is are you doing it for more dollars & swinging for the fences or just for the experience? Having been a successful small business owner, it is clear to me that going back to work and reporting to some $400k/yr executive who’s never created anything or risked his own capital would be extremely challenging. I do like the idea of you leveraging your entrepreneurial spirit and diving into the start up world. You’ve been broaching the subject for a while…just do it!

        1. The money and relative stability is definitely one of the benefits of going back FT as month to month revenue swings can be very volatile, and therefore very demoralizing to entrepreneurs who do nothing but give 110% every single day.

          That said, I feel like two years of consulting for various fintech companies and going to a dozen meetups and events has given me as good of an idea as possible on what I’m willing to do.

          I won’t have a problem working for a $400K/year executive who’s never risked capital or created something of their own b/c working in a startup is all about that, and the most entrepreneurs pay themselves here is $200K/year or so! :)

  44. It’s hard for us to really say because we’re not coming from the same place you are. We can read your story and read your feelings on the subject, but we (you and your readers, not you and me) are going to have such different feelings on the subject because we have such different wants and experiences.

    Honestly, if I had achieved early retirement via passive income, I would never want to go back. Perhaps it comes from working at busy branches with spoiled and nasty customers walking through the door all the time, but I’d rather be bored than stress over sales goals, saying the right thing to your boss’s boss, dealing with push-back from customers who think the rules shouldn’t apply to them, being up daily between 5:30 and 6:30 AM, all for a pretty low pay.

    And just because you don’t have a full time job doesn’t mean your life HAS to be boring, right? People who are bored during retirement make life boring for themselves.

    Also, I have a different opinion from you because I have different experiences than you. Not better or worse, but just different. Many of us pretty much come from a low-on-the-totem-pole position. I’ve never gotten the corporate card to wine and dine clients (and save money on my own lunch expenses). Instead we’ve gotten in trouble for laughing too loud during our lunch breaks and using our cellphones in the breakroom when we’re off the clock. Obviously every job has rules and things we can’t do that we wish we could and I understand that, but I don’t think I would subject myself to a company’s arbitrary rules for 40+ hours a week if I had achieved sustainable early retirement.

    I wouldn’t even go back to the revenue-sharing sites I used to write for now that I have my own blog.

    I’m not saying that you definitely shouldn’t, but that when you ask our opinions on the subject, it’s likely not going to be applicable to you because we’re coming from such a different place.

    Plus, unless there’s a contract involved, I don’t think “the paycheck” is that secure at all. Your employer can fire you at any time for any reason, right? I’ve seen transfers and layoffs and we have things that can–and have–get people terminated on the spot for honest mistakes. During the recession, people relying on their paychecks for money were suddenly left with nothing while people who owned shares of ExxonMobil saw their income safely increase. I’m not sure how much “security” that paycheck provides when you really break it down.

    Besides, aren’t you doing Uber right now?

    ARB–Angry Retail Banker

    1. To me, it seems like Sam is feeling bored and needing a new challenge. I understand that sentiment completely as I get stir crazy with most endeavors after 18 months-3 years and crave new surroundings and new obstacles to overcome. ARB, your posts seem to frequently convey a lack of job satisfaction and disenchantment with the salary you are making. So much so that your handle/avatar embody this and your discontent has taken on an online life of its own. Perhaps you could benefit from some of the career ‘wanderlust’ Sam is currently experiencing. New field? New company? Who knows. I wish you well on your transition from Angry Retail Banker to Content Retail Banker. Or Happy Something Else. HSE>ARB.

      Sam, ARB is right in that you’re likely to receive a shotgun blast variety of responses based on your readership’s diverse backgrounds. Most who say no likely haven’t experienced the freedom you have over the past 4 years so they are naturally inclined to vote for the option that they desire, but can’t have. I would be one of those people myself, however, I completely understand the need for change of pace and new experience. The corporate ladder is definitely a grind, but getting your foot firmly on the next rung is a massive self-worth booster. I can see how it would be difficult to replicate that in your current environment.

      I say do it and write about your success/failure of a decision! That way, we can all learn at your expense!

    2. ARB,

      I LOVE reader’s opinions for the exact reason you state, because they are unique. I re-read your feedback three times, that’s how much I appreciate it.

      I’m here responding to comments at 6:45am because interacting with all of you about a subject I really care about is very fun and rewarding. If I went back to work FT, I would still do this because work doesn’t start until 9am+ at most startups!

      The key really is finding the right fit. What if the number of your whiny, entitled customers declined by 80%? What if you got a raise and a promotion? What if most of your colleagues were all really cool and inspiring to work with? What if you guys built a great product and got acquired for 5X the company value when you joined and participated in the windfall?

      We can always dream, right?

      Regarding Uber, it can be fun at times if you meet some cool people. But overall, it is very solitary work, just like managing websites. 5 – 10 hours a week is nice to make some extra income, meet some new people, and pick up some new stories to write about. Any more and it feels like a chore after the initial couple months of discovery.

      1. Bryan @ Just One More Year

        @ARB – As usual, you get to heart of the matter. I agree with your sentiments. :) 

        It is hard for many of us trying to leave employers behind to hear you considering jumping back in as an employee. This is very counter intuitive to the PF community. Yet I can understand your reasons why it might be ok for you to do that now. I have been following you for years and have seen this progression in your blog, consulting, and side gigs like Uber. (New book idea: “How to go back to work for the man doing what you want, when you want, for what you want to get paid”)

        For me, I have worked off and on from home for nearly 15 years. As cool as it might sound with many of your readers, you do lose the human interaction and feeling of being part of a team. I too have often thought about working part time here locally just to get the interaction that is missing in my virtual world!

        1. You will LOVE working part-time among people 1 – 2X a week. I found a really great balance consulting 2X a week in an office. Unfortunately, they hired someone FT over me, and then fired the person three months later. By this time, I decided to move on b/c I don’t like waiting too long for anybody.

  45. I agree with everything you’ve said, Sam. I love working with a team of smart, hard-working people every day. I love goofing off on Slack. And having interesting people to have lunch with. Working in tech rocks! I think you should definitely consider the right financial tech opportunity.

  46. I heard an interview with the guy who created Dilbert. He stayed at his job for something like 8 years after Dilbert went huge. His reason was that work became fun when it was no longer essential. He just did what he really wanted, and what he thought was best, without fear of losing his paycheck. If you find a company that values your style and will give you the freedom that you need I’d say go for it.

    1. Thanks for sharing! 8 years is a long time, and clearly, Scott Adams is making millions from his creation.

      Work is definitely more fun if you didn’t have to work. Imagine working on things because you enjoy the work and know you can add value. Meanwhile, you had your side hustle that’s in syndication make you a healthy paycheck while you also earn a healthy paycheck at work. Amazing!

  47. You may want to reconsider expanding FinancialSamurai, having others to collaborate with may fill the void. From reading your thoughts it appears you are really looking to be part of a team again. I haven’t been able to cross to the other side of FI yet, but when I do I plan to continue to work on a part time basis. I think being part of a team will be critical for being held accountable and filling a sense of purpose.

    1. Agreed.

      But no matter how much collaboration I create to build new features or produce more content, it’s still mostly virtual.

      I really think part of the reason why I get this itch to go out for a two hour drive with Uber is due to the potential new conversations I’ll have with people.

  48. InsiderAccountant

    Are you sure you didn’t drink too much of the employee Kool-aid?

    I never thought I’d see a post like this from you and worry that you are looking back on the past with rose-coloured lenses!

    Be careful what you wish for – I’d rather be retired with your net worth than be an employee!

    1. I only drank freshly squeezed orange juice at Google. If they had fresh watermelon juice and Hawaiian mango juice, maybe it would match closer to Kool-Aid.

      I’ve seen both sides of the fence. I liked working 75% of the time while in finance, and it was a massive pressure cooker. After spending two years consulting in the fintech space, I think I can up that percentage to 85% partly because I’ve completed the challenge of building a lifestyle business. Unless something disastrous happens, my little online business will survive for years to come.

      Being a part of a team is something I really enjoy.

      How long have you been working, and what do you do for a living?

      1. I’ve also been on both sides of the fence and while being self employed provides lots of freedom of time you also miss out on being part of an organization as you say. There are certainly pros and cons for both. I think self employed beats working for someone but you also need to find your community to feel part of something, whether it’s in your work or during your free time. When I was an employee and got home from work I mostly wanted to unwind and be away from people but as a self employed I find myself craving organized companionship.

          1. Sam – I am 19 years plus now with the same firm and have had a decent career. However, I am the opposite of you. Complete burnout for reasons that I don’t to bore people with. I did that in a post a while back.

            I totally support you going back but find the right fit. The good news (great actually) is that you have the flexibility to only accept something that will clearly work for you.

            I wish some of your entreprenurial spirit would run off on me!

            1. You don’t have to explain feeling burnt out after 19+ years with the SAME firm. Trust me, I know exactly what you are thinking.

              The good thing for you is that hopefully your retirement accounts are robust, and if you ever leave, you will / should have a fantastic severance package if you do it right!

              Maybe the entrepreneurial spirit is innate. But I think the desire to choose, to be free, and test the limits is innate in us all!

  49. I don’t think it’s a bad idea. It’s a better idea than ever given the flexibility you have created if you ever decide it’s not for you or if you wanted to go part time. You seem like you’re in a position that most people yearn for-the ability to work not because they have to but because they want to.

    1. It is a joy to work on something because you want to vs. because you have to. If I was hiring someone, those are the people I would always look to hire.

      If I do go back, I want to make at least a 3 year commitment. Which is why finding the right fit is so important. I used to laugh at folks who moved around every 3 years in the tech space after 11 years at my previous shop. But after seeing first hand how much change there is in the tech industry, 3 years is pretty decent!

      1. I think it’s a great idea your posts lately seem to ooze that you feel a lack purpose. There’s nothing wrong with a painter going back to painting. Just make sure its what you love doing.

      2. architectdave

        Hi Samurai Sam, I’d strongly encourage you to reconsider going back to fulltime employment unless you see that soon you will *have* to. After 35 years of high-tech life in many roles and companies, “living the dream” with my $M house in Silicon Valley, I have become numb to any sense of what the peace and freedom of setting my own daily course might feel like. Certainly I am sure it can’t be worse that the crazy/fiercely competitive hustle that i do (and apparently you did) for 70+ hrs/week. I read your blog with very great interest and am thankful that you do it.

        I also noted your good post about not getting slow – for sure, I feel the heat every day, and see the hunger of the younger’uns brashly chasing up the ladder of importance and power. Even though I’m still top of my game and can still outpace most others in my area, i am gradually feeling increasingly burnt out and now, frankly, I’m kinda getting done with it.

        Maybe for both of us, grass looks greener but when one gets to the other side, its same grass only separated by a fence.

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