Filling The Void In Early Retirement With Part-Time Work

There is a void in early retirement you might experience. This void in early retirement needs to be filled if you want to feel happy and productive.

Over the past one and a half years since leaving Corporate America I've done some deep thinking about early retirement through posts such as:

When you're used to working 12 hour days every day for 13 years it's very hard to suddenly downshift from sixth to first. You'll blow up your engine if you do. There needs to be a gradual progression whenever large life changes are made.

Filling The Void In Early Retirement

Hawaiian Sunset With Sailboat In Retirement - Sign up for my free Financial Samurai newsletter here. Also, check out my top financial products page to find the best products for your finances.

The first six months of retirement I was second guessing myself on whether I made the right move. I had just turned 35 years old and short-circuited my career in finance. I wanted to travel and do my own thing. I worked my ass off to finish writing my book on “How To Engineer Your Layoff.” Therefore, I could at least say that I produced something meaningful if all went to hell.

My doubts began to calm down during my second six months of retirement. I was able to take a 2.5 week long business trip to Europe to research the happiest people in the worldTraveling while writing and maintainigg my online business helped crystallize why I decided to leave Corporate America in the first place – more freedom!

The final six months have been an absolute blast. With six weeks this summer in NYC, Mallorca, and Switzerland (links to FOMO, finding perfect summers, and eradicating apathy) and four weeks this winter in Hawaii all the while working of course. There's absolutely no law against having fun while traveling to understand different cultures. The key is moderation.

One Thing Missing From The Accomplishment Belt

We always want what we don't have, and what I don't have on my resume is working for a startup.

I've lived in San Francisco for 12 years now. During this time I've seen a number of fantastic Bay Area startups go public. I remember seeing Sergei Brin from Google speak about his company's growth during an investor roadshow luncheon back in 2004. My firm was one of the many joint book runners. Google has gone on to be a 10 bagger and created thousands of multi-millionaires and several multi-billionaires in the process.

In the meantime, financial stocks basically went nowhere since 2000 thanks to all the financial meltdowns. Financial services professionals got paid OK during this time. However, it sure would have been nice if we got paid OK and saw our company's stock rocket higher like our tech/internet brothers. By 2008, it was clear that not only would financial stocks continue to perform poorly with increased regulation, but compensation was also going to decline. It wasn't as fun to be in investment banking anymore so I left.

Startup Life In San Francisco

To live during San Francisco's internet golden age and never experience first hand what startup culture is like would be a shame. That would be like living in New York City and never trying your hand in finance, food, acting, or law. I've always imagined startups hum with a casual dress atmosphere dominated by enthusiastic individuals working nonstop towards making their product come to life. I want to contribute to such a culture.

Some of you may be wondering what's wrong with me since I'm in the thick of my very own startup, my portfolio of sites on the web and, a finance advertising network. I'm the CEO of the business and make all the decisions.

The business could sell for millions of dollars if I generate enough revenue. But selling isn't on my mind. I treat my business like a companion for 2-4 hours a day during retirement. I've come to realize that despite a 10 handicap, I dislike golf. I always feel the need to be productive for just a little bit every day.

The Solution To Filling The Void In Early Retirement 

Companies have become much more careful in hiring full-time employees because of the difficulty of letting employees go if things don't work out. The proliferation of freelance workers has also made it harder for folks to find full-time work. When you don't have to pay for health insurance and unemployment insurance, provide a 401(k) match, or give vacation benefits, it makes the decision to hire and fire someone much easier.

There are too many disaster stories when a company realizes they've hired the wrong person after several months. They can't do anything immediately to get rid of them without a potential lawsuit due to the need for enough documentation for misconduct. You'd think “at will employment” would make firing easy. But the reality is much trickier when friendships, feelings, and politics get in the way.

If you're not looking to work primarily for the money and benefits, the solution is for employees to work part-time. I used to daydream during my last couple years of full-time work how nice it would be to always get Fridays off every week plus my six weeks off a year. If that were the case, I'd probably never leave! Perhaps the next best thing is to simply work part-time for several days a week for part-time money.

The Benefits Of Working Part-Time In Retirement

* Flexibility. The three or four day weekends, every weekend can suddenly become a reality. Perhaps you can negotiate half days, or the ability to telecommute from home. For mothers and fathers, I imagine part-time work could be ideal, especially if the spouse works full-time. Flexibility is very important for employers who would like to keep costs down and have the option of terminating if the fit isn't good.

* Participation. Although you are a part-time worker, you still get to participate in luncheons, company parties, business meetings, and interact with people. One of the hardest things about running my online business is that it gets lonely doing everything on your own sometimes. Employers should try and hear perspectives from part-time employees more often as they might be less afraid of speaking their mind. Part-time work is filling the void in early retirement.

* Income. Usually people associate part-time work with low pay, but that's not necessarily the case. Often times freelancers can charge a premium because the employer does not have to pay for all the benefits and taxes associated with hiring a full-time employee. Whatever the going rate is, generating some income is always welcome for your time spent. Employers will feel better knowing that their costs are associated entirely with the production of their hire.

* Visibility. It depends on how you negotiate the contract, but you should always come to an agreement about how long your part-time work will last. Let's say you know you have a lot of free time during the summer, you can potentially fill your summer void with a three month part-time contract. If employers are not absolutely sure about hiring you, but still see value in your work, three months is a perfect agreement because it gives both the employer and employee an out. Everything is bearable and negotiable if there's an end date.

The Downsides Of Working Part-Time In Retirement

* No benefits. I have a feeling the majority of employees take for granted their company benefits such as short-term disability, life insurance, health care benefits, 401(k) match, and paid vacation days. It's easy to not appreciate such benefits because they don't have specific dollar signs ascribed to them. As an employer, I see what all these benefits cost, and it isn't cheap at all. (See: Subsidy Amounts By Income For Obamacare)

* No stock options. If your company hits the big time and you work for a long time as a part-time employee, you're probably going to feel pretty bad when you see all your colleagues make big bucks and you get nothing. But the nature of part-time work is that it generally only lasts for under a year. If you are great at your part-time job, more than likely the company will offer to hire you full-time with all the benefits and some stock options. If not, you didn't want to work long term for them anyway.

* Less respect. Your colleagues may treat you with less respect because they think you're not working as hard or will be gone before anything you do really matters. It's up to you to demonstrate your seriousness and abilities to command respect for your work. Lacking acknowledgement or respect was one of my biggest peeves about working in a big corporation. I'd often prefer acknowledgement over a pay raise.

* No promotion. You'll always be exactly the way you are at the company, a part-time employee with no title, and probably not even a business card. When I was working full time, every promotion I received felt the same way as when I got an acceptance letter into college: absolute euphoria! Although the euphoria didn't last for longer than three months, it still felt wonderful. As a part-time worker, the biggest promotion opportunity you'll have is being offered a full-time position if you really love the company.

The Decision To Work Part-Time Or Not

Thesis: Work would be so much more fun if you didn't have to work. I'm curious to know whether or not this is a reality.

Now that we've discussed the pros and cons of part-time work, I'd like to ask you whether you think I should work part-time at a financial tech startup. The idea would be to combine my background in finance with my current interest in technology during my free time.

Even when I'm traveling, my day is always done by 11am if not 10am since I get up by 6am every morning and have a self-imposed four hour work limit. I fill the rest of my day with lunch with friends and tennis since I don't have a family yet. Of course I check my phone to respond to comments, business inquiries, and interact with the community throughout the day, but that's about it for my online activities.

Time Is Valuable

I don't need the extra income, but my time is valuable. For example, I charge several hundred dollars an hour for my personal finance consulting practice. Consulting with two to three clients a month is an excellent use of time because I get to help others directly improve their financial well-being. Earning income is always a positive because it boosts savings, which studies have shown leads to a direct increase in happiness.

The company that ends up hiring me will get a hard working, collaborative, out of the box thinker who is results driven. I will never fail due to a lack of effort. And because I've already achieved financial independence, I no longer have an ego that may generate interoffice conflicts. I'd happily work for someone my junior and promote my colleague's work so they can succeed.

Who knows. I may love working at the startup so much that it may lead to a full-time offer and a whole new joy in life. Even if the part-time job doesn't result in a great match, I'll have met new contacts in the community which could lead to other opportunities.

Related: The Negatives Of Early Retirement Nobody Likes Talking About

Resources For Filling The Void

* Negotiate A Severance Package. Never quit your job, get laid off instead if you want to move on. Negotiating a severance package provided me with six years worth of living expenses to help me focus on my online media business. Check out my book, How To Engineer Your Layoff: Make A Small Fortune By Saying Good-bye. It's the only book that teaches you how to negotiate a severance. In addition, it was recently updated and expanded thanks to tremendous reader feedback and successful case studies.

* Start your own business. One of the best ways to keep yourself busy in retirement is to start your own website like mine. It used to cost a fortune and a lot of employees to start your site. Now you can start it for next to nothing with Bluehost. Brand yourself online, connect with like-minded people, find new consulting gigs, and potentially make a good amount of income online one day by selling your product or recommending other great products. Not a day goes by where I'm not thankful for starting Financial Samurai in 2009.

Pro Blogging Income Statement
You can start your site for next to nothing and potentially make a lot of extra income. This is a real example.

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56 thoughts on “Filling The Void In Early Retirement With Part-Time Work”

  1. Pingback: Top Financial Resolutions For The New Year | Financial Samurai

  2. You’ll regret it.

    Wanting to work for a startuo because you haven’t is like wanting chickenpox because you haven’t had it yet. There may be long term benefits but it’s incredibly painful getting there.

    Most startiups:

    – fail. No winning the IPO lottery.
    – are incredibly chaotic
    – work very long hours – part timing is not part of startup culture – 24x7x365 is
    – pay very low
    – have bad benefits

    If you want part time work at a startup, become a consultant. You’ll still have the interaction with the people, and exposure to the chaos and energy, but will be paid much better, and still be able to retain your freedom.

  3. I think you should go for the part time work. It seems you absolutely loathed your former job on Wall Street which has probably given you a really negative impression about work. A job that is a better fit for you should enhance your life, not drain it. This is a chance for you to try something new and meet some new people. For me, I really enjoy the social aspect of work. We just had our holiday party and I got to watch my boss trying to dance. It definitely brightened my day.

    1. I actually didn’t loathe my former job at all. I was just getting bored after 13 consecutive years of doing the same thing. I admire anybody who can stick with one thing for so long. How long have you been doing your current duty?

      I just felt so much more excited to write online so I naturally went to what made me happiest.

      1. Oops. Sorry, I shouldn’t have assumed you hated your previous job. I might have been projecting. I used to hate my job and day dreamed of early retirement. It’s actually what got me into PF blogs. I switched some of my responsibilities up about 2 years ago and have been enjoying it much more recently.

        1. No worries. How long have you been doing your job for?

          I’ve been fortunate to have always found excitement in what I’ve done, and I attribute that to opportunity. Then again, I did hate working at McDonald’s at 6am for $4/hr!

  4. Sam, whatever choice you make will be the right one (for you). You are in a position that most people will never be in. In general, people either have time and no money, or money and no time. You are in the enviable position of having both time and money. Remember the saying “Nothing ventured, nothing gained”.

    Another cliché states that when one door closes another opens. Don’t be afraid to open this door – you might find something pleasantly unexpected on the other side. Heck, you might even meet the future Mrs. Dogen in your new endeavor. Good luck with whatever direction you take!

  5. Not exactly part-time, but two years ago, I reduced my work schedule by 10% by taking every other Friday off w/o pay. After income tax and FICA, it’s only something like a loss of 2.5 hours net pay per week. Every other weekend is a 3-day weekend! That give me 26 unpaid days off per year + 15 paid days off per year, and I keep full benefits! I’m thinking that I’ll soon reduce my work schedule by another 10% and take every Friday off (unpaid). This is an actual policy at my employer and is open to all employees. My schedule has, however, induced some coworker jealousy.

  6. Sam, somehow I completely missed the fact that you were so young. Pretty amazing stuff. Have you ever thought about taking a class or something — like the one class you wish you would have taken just for funsies? If I had a lot more financial independence I think I would go to school for fun but I’m too busy paying back loans from all the school that was not fun. Also, I think a start up would be lucky to have you but then you’d have to actually go to work when they said and ugh, that’s no fun. ;)

    1. Hi Cat,

      I thought about doing a journalism fellowship this summer but couldn’t get in due to my lack of journalism background. I would think they’d welcome a blogger who built a brand and some decent traffic online to help the dying old media industry, but guess not. It’s very hard to change corporate inertia and I realize partly why traditional media is dying.

  7. In your shoes, I would teach part-time as an adjunct. And run my own money. That would probably be enough to fill my time. Oh that and my 3 year old kid. Good luck with your decision! I think part-time work is indeed the answer.

  8. You’re in the perfect position to pursue just about anything you like. If you think working with a start-up sounds fun, I’d go for it! Just know that most start-up’s fail and not to take it personally.

  9. Also as someone pursuing an MBA myself, my guess is that people want to do something with their degree and try to change the world (so to speak). Probably not going to have a fortune 500, at least not as a business person. Maybe in product development…

  10. Everything depends on your purpose! The money is probably incidental, but the experience can be worth it. You can use it to network or change careers. Most companies will hire people who volunteer or work part time. It is similar to the college students who get internships.

  11. I’ve worked at startups and large corporations and I didn’t like either. I like the smaller sized companies that are not quite start ups anymore.

    My startup experience was working out of an apartment in San Francisco. The expectations and hours were terrible. At first I felt I was being compensated for my time (averaging 60+ hours a week, which isn’t normal but could be worse). After 7 months or so the company wasn’t doing so well so everyone in the company had to take a 50% pay cut. Instantly the desire for me to work my ass off disappeared. It didn’t help that since it was such a small company one of the office people discovered that the owner of the company was still making around $300K per year after the pay cut and to try to sympathize with employees he used the tactic of “I may need to take in roommates to help cover my own expenses” in his 1.3mil house…. Yes I guess I’m a little bitter over this one still, but only cause he was a jerk.

    I did work at another startup like company and while I liked the people and the atmosphere, the benefits weren’t the best and money was always tight. Raises were almost non-existent or delayed by 7 months after you were supposed to get it.

    Basically I don’t see startups not working you way more hours than you expect. I find that most try to squeeze blood out of rocks. You only have so many resources, you can’t expect 1 person to do 2 peoples jobs for extended amounts of time.

    Right now I’m in a smaller company that is more established. The atmosphere is similar to a startup because they want to draw good people so there’s a lot of little perks that help keep people happy, and one of them is trying to balance workloads cause no one is useful once they have burned out. I’m never going to hit it rich with stock options, but since there’s under 100 employees I still get input that doesn’t fall on deaf ears. They are also small enough to want new and fresh ideas that might help them.

    You didn’t ask for it but as for input on Large companies…. I worked for Sun Microsystems, every week we had meetings about what we were putting off until next week. I felt like nothing got accomplished and time at work went by so slowly because there was nothing to do. It was a place where ambition went to die.

    I think you have to find your “Goldilocks company” of what you want and how it fits you. Personally I don’t think it’s a start up because my experience with start ups is that the hours are not going to fit with what you are looking for. Maybe you get lucky but all the stories I’ve heard seem to match my experiences as far as hours are concerned.

    1. Zee,

      I really appreciate your feedback! I had many software engineers in my B-school class who were just dying to get out of engineering and into sales or management. The Saturday campus was at Sun micro in the South Bay funny enough!

      I’m trying to figure out whether there is selection bias here eg only people with really bad startup experiences leave comments? If startup culture is so bad, why does every top MBA and tech employee want to join a startup?

      I do feel that by going into work instead of telecommuting I’ll be able to better manage my 20-25 hours a week part-time. If they wanted full-time, they seek a full timer.


      1. That’s why statistician have it so tough!

        My uneducated guess though would be that top MBAs are seeking riches that are unlikely to come to fruition. After the company receives a couple of series of funding you can actually make good money at a start up, if you have a specific skill set that they need. Typically that’s on a consulting basis, my personal experience.

      2. It’s highly possible that there are more people with bad start up experience reading your blog. I don’t think there are many people who were at facebook when it was a startup that are reading personal finance blogs which are geared towards financial independence because they have already reached financial independence.

        I joined a start up because I was young(er), and I the employer sold me on the potential of the company being possibly paying out huge. I was also naive and didn’t see the flaws of the company. I learned a lot there with trial by fire, but more importantly I learned what was actually important to me by working there. I appreciate my own time and I learned that sometimes it’s not worth putting up with a bad boss, and that: happiness > money

        (though I’m sure there is a tipping point where I would choose money over happiness, but the bar was raised higher)

        Also the stress of a start up would weigh on my decision to ever go back to one.

    2. @Zee: “I worked for Sun Microsystems, every week we had meetings about what we were putting off until next week. I felt like nothing got accomplished and time at work went by so slowly because there was nothing to do. It was a place where ambition went to die.”

      I’m in the same situation at my 900-employee workplace. A departmental restructuring recently increased my meeting time to more than 10% of my work schedule, plus the random committees I’ve been assigned to. I can’t believe these senior managers, all MBAs, waste so much time w/ unnecessary and unproductive meetings. I believe that they think that they’re being good managers by giving some of their time to the underlings via meetingsl only thing is the sr. managers are in love w/ their own voices. In the last year, my ambition has greatly declined. Today, I took a two-hour lunch and spent six hours surfing the Internet. I did not accomplish one bit work for my employer, and it does not matter one bit to my employment status or compensation.

  12. Yeah, I can’t imagine a start-up allowing part-time…either full-time or no time.

    How about learning another skill? I taught myself how to do plumbing and completed a plumbing install on a new house. Passed all inspections. Comments I received were, “awesome.” Next up, A/C installation and learning MIG welding.

    Good skills to have Sam as a family man…women find it sexy! :)

    1. Haha, nice. I have the great skill of knowing how to find an expert plumber and AC technician and getting him/her to come over in a short amount of time to fix things.

      So perhaps you point to something special. If I CAN find a start-up allowing part-time aka freelancing/contract work, then that’s a treasure to embrace!

  13. I take it this means you are being recruited. How about instead of part-time, which will never happen given your personality, why don’t you set a full time contract for two or three months and then you can revisit whether you want to continue after that? The happiest people that I know I are the ones that work part of the year, not part of the week (or day).

    1. Might be tough to hire someone full-time for 2-3 months vs. hiring someone in a consulting/freelance capacity for 2-3 months. Depends on HR. The company itself wants to also start off slow too, and I’m not 100% sure I want to get back full on into the thick of FT work. We’ll see.

      1. I meant as an outside consultant with 3-mths contract (for example)… and a specific project with a specific goal. That way you can comfortably depart, knowing you’ve seen the project through. Just a thought.

  14. I have workaholic tendencies so I can understand your curiosity and interest in taking on a part time job. I think I will always need or want to have some time of work to do as long as I’m not raising kids. But I would be very picky with the type of work I’d chose after I retire from my day job. I think it’d be cool if you try out a part time gig at a start up if you can maintain flexibility and won’t get stressed out. Increased stress wouldn’t be worth it.

    1. My stressometer is registering like a 1 out of 10 right now. I think I can comfortable handle a consistent 6-7 out of 10 before I start pulling back. But once you go through the stress of working on Wall St., seriously EVERYTHING seems pretty easy afterward.

      Like warming up with two or three bats before you get up to the plate.

  15. I think it’s a good idea for you to try working part time. It seems like you have extra time so why not try it out. Maybe you’ll like it. Yeah, I don’t think a start up will let you work 4 hours/day either.
    I will probably work more once our kid starts school full time. I don’t think I’ll work for other people though. I am way too happy being self employed.

  16. Hi Sam

    As a former startup member, I felt I had to chime in. I’m not familiar with the finance industry, but at least in tech in the Bay Area, startups are completely toxic, IMHO.

    The sales pitch is great, but you’ll just be ridden dawn to dusk, the pay will be low, and 99% of them fail. Oh, and don’t think that being part-time will save you either. That 20 hours per week will rapidly expand to fill your available time.

    I understand that there may be a void to be filled after early retirement (even someone as gung-ho on FIRE as I am can see that), but joining a startup is just never the right move. Especially since there are so many other options that would be more productive.

    One thing I’m looking at, post-FIRE, is “Teach For America”. Well, that and “Pina Coladas on the Beach 101”, but I’ve heard that you already took that course. :)

    1. Jason,

      Just the negative answer I’ve been looking for to keep my eyes wide open! Did something really bad happen to your startup? B/c labeling all the startups as “completely toxic” sounds extreme b/c the startup euphoria is high and mighty here in San Francisco. It is part of our culture just like eating fine cuisine is part of Manhattanite’s culture!

      I believe the 20-25 hour day could expand beyond that allotted time, which is why I plan to actually go to the office, focus, work, and leave work at work as best as I can. Telecommuting might actually be much worse for setting boundaries.

      I was having some mimosas on the beach in Oahu during our off-site last week. It was wonderful. Let me know how Teach For America goes. I feel that by consistently writing about financial topics here, I’m in a way doing my part to help.

      Please tell me more about your negative startup experience! Perhaps a guest post is in order if a comment cannot suffice!


  17. There’s nothing wrong with working just for “fun” and to make another lovely dollar or two.

    Many early retired people turn to volunteering in order to feel productive. I think the right paid employment would be better than volunteering. When your employer is paying you top dollar, you’ll likely be more challenged than in a volunteer position where they don’t monetarily value your time very highly.

    I wouldn’t mind a 20 hr/wk limited term contract of 3 months every now and then. It’s just hard to find something that is really 20 hours (and doesn’t slide into 30-40 hours for 20 hours/wk pay). The only things I have found tend to pay about half what I used to make (which was nowhere near the Wall St. salary I assume you were pulling in during your finance days).

    In the meantime, I have blogging (writing, advertising, tech side) to keep my mind engaged. It’s not bad because I can not touch the blog for a day or two and it doesn’t matter. Or if I want to sit down and crank out a 2000 word article and spend 4 hours doing it, that is also an option.

  18. Startup Jumper

    @Startup Jumper

    The last report from suggests I’m discounted between 10-25%. They tout stock options to make up the difference, but that’s a hard sell since we aren’t traded yet.

    Opportunity cherished :)

    1. 10% is too bad. A 25% discount starts getting painful since after 4 years of work it’s like losing 1 full year worth of salary.

      But given you enjoy it so much, with a call option, it’s not too bad at all.

  19. I’d do it if I were you. The main metric for me in a similar decision would be flexibility. I would want maximum flexibility. And therein lies the problem for me in my early retirement. I retired from a life on Wall Street in NYC. (51 years old). Moved the family down to NW Arkansas. Wife is in the middle of her career. 5 year old boy in pre school kindergarten next year. I don’t want a full time job, nor do I want a part time job that’ll I’ll have to be tied to. Nothing I can think of makes me excited.

    So I’m now in the process of buying an existing car wash. Never done anything like it before. Should be pretty flexible. Great return on my money IF I can keep revenues were the are/have been. Heading to closing in a week. Very nervous about the decision. Small risk of a failure I suppose, but it ought to be decent part time job. Maybe a lot of time there in the beginning, but it’s runs itself with 2 part time guys. I want to be able to spend a week or 10 days away from any work I do from time to time.

    You are in a fortunate situation and have many skills. Do it. If you don’t like it, move on.

    1. A fellow ex-Wallstreeter! Nice. If you worked on Wall St until 51, do you really need to work another day in your life, especially living in Arkansas? Depending in how many years you worked, if think you’d be making it rain!

      1. I worked for myself in derivatives trading. Some blockbuster years, some decent years, and plenty of break-even years with high expense/NY living. Did well enough–certainly enough for my simple Arkansas needs, but my wife has a worrying personality. Happy wife = happy life. And she hates idleness (I love it!) Not a bad idea to have a cash flow from a side business with low labor input I suppose. Buy myself a ‘job’.

  20. Roger is right. I have been living in the valley since the heady days of dot com and have worked for 6 different start ups. 4 of those were abject failures. One went public and one was bought by one of the valley giants. I made a grand total of 200k from both. I had to take pay cuts (2008/2009), job loss (2001/2002) etc along with crazy hours and intense workload. Many of those start ups did offer 401k/good benefits. Of all my friends who graduated from grad school with comp Sci the financially better off are the ones who stayed with the Microsofts and the Oracles. They got steady promotions and built a sizeable nest egg. Since 2011 I have been working for one of the valley giants with good work life balance… My point is that not every start up is a google or a facebook! The chances of you working for a future failure is lot higher!

  21. I have always thought that when I retire early, I will donate my time. I will be in a situation where I don’t need more income and I would love to donate time to something I think is worthwhile. The great thing about volunteering, is that you can switch up what you are doing. One year, you might be doing strategy for a non-profit organization and the next you might actually be getting your hands dirty and getting out into the community.

  22. I have never been in the corporte world. I have always been self employed or had my own business. I think the optimal life situation for me is when I can create companies to run by themselves and keep creating new companies in my free time. I have a few businesses now, but they aren’t running by themselves yet!

  23. The stock options aren’t really worth it these days. Most startups don’t really hit
    grand slams. For every Google, there are many out there that fail, get bought out,
    or go public to not much fan fare. Better off to just contract and get bigger $$$

  24. Startup Jumper

    Hi Sam,
    I decided to relocate to the Bay area about a year ago to explore my desire to experience a start up after working for a large company for the first 7 years out of school. The workload is immense, but the personal satisfaction and professional growth I’ve experienced in the last year have been greater than anything I imagined. Getting to interact with the key decision makers and being sought out to share my perspective on business decisions and seeing the impact of this on the company is something I never thought possible working as an engineer in manufacturing. I have aspirations to eventually start my own business and I felt like being a part of foundational business crafting team as I am now would be the best way for me to understand more specifically the challenges that come along.

    It is tiring and demanding though. If you can find a way to do this part time, I would certainly encourage you to go for it. What’s the risk if you negotiate the end date anyway? My one warning might be that it’s an infectious environment and you may want more!

    1. Sounds like you’ve got the best of both worlds! Any lucrative exit strategy for you in the near future? If so, where would you go?

      I’m counting on an infectiously positive environment to keep me going beyond a 3 month part time window.

      Work is great when the environment is great and progress is being made.

      1. Startup Jumper

        I’ve been considering my exit strategy recently, since we are now in the thick of launching our first product. How that goes will greatly influence when and how I exit. Right now I am focusing on wringing every last opportunity for development to better round out what I can offer to future positions. Cultivating relationships with coworkers and soaking up as much as I can from my mentors are paramount due to the very close-knit community of Bay area medical device manufacturers.

        When I do exit, it will most likely be for another start up, as I currently lack the confidence to follow in your footsteps. Regardless, the work I am doing is so fulfilling, even with the long hours and mediocre pay, it’s hard for me to imagine not doing this for a few more years. If I were to look for alternatives for where to spend my valuable time and energy in the future, it might be with an NGO or international aid organization, as providing people with life-saving medical care/devices and helping to fill essential needs are the passions that motivate me.

        Compensation may not be as competitive as with a larger company, but it’s enough to let me meet my aggressive savings goals and still feel like I’ve made a meaningful contribution at the end of the day.

        1. What is your “mediocre pay” discount to market if you were to work for a more established firm?

          Cherish the enthusiasm of work for as long as possible bc it eventually fades. But with the increase in your financial nut, things get better.

  25. Sam, I dream of being in your position, as do a ton of others I’m sure. My desire is to be able to spend more time at home, teaching my kids, instead of spending 10-11 hours a day outside the home. I have two kids, with another on the way, and would love the ability to have a greater impact on their development, perhaps even allowing my wife to pursue her writing and editing career. We plan to home school ours, since my wife and I were both home schooled ourselves and loved it. But I’m convinced that children need more male influence in their schooling, as opposed to mom being the teacher and dad just the principal.

    This is a great post, and I think the question you ask has a lot to do with what people value in life, because that’s what comes to the surface when the money is de-prioritized.

    1. If I had kids I’m pretty sure I wouldn’t want to spend the 20-25 hours working. I feel I need to maximize my freedom as much as possible before settling down.

      One insight I can provide is that everybody gets used to their financial and life situation no matter how good or bad things are. A lot of it is about feeling productive and not wasting time since we only have one go around. I also have a constant need for a challenge and excitement.

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