Step As Close To The Edge As Possible To Love Your Life More


If you go close to the edge, you'll realize what's possible.

In my quest to make my life worse, to ultimately make life more enjoyable, I've continued to look for full-time work to test my resolve. 

Every time I step into an interview room, I change my mindset from a guy with financial freedom, to a guy who seriously needs to find work to pay his bills. It is sadistically exhilarating for me to get back into begging for money.

During the holidays, one potential employer locked me up in a conference room for six consecutive hours to interview and video conference call with eleven different people. Eleven! That's ridiculous, especially since I didn't have a break for lunch or a break to go to the rest room.

Talk about a test of endurance – simultaneously being hungry, having to piss, and trying to charm a stranger. Freaking awesome!

Close To The Edge And Subject Myself To Torture

Some might wonder what kind of idiot would go back to work when his passive income surpasses his living expenses by at least 50%.

First of all, it's hard to interview well without practice. I've been out of practice for almost four years now, so I figured at the very least, I could brush off the cobwebs. 

When opportunities arise, it's all about being prepared. It's kind of like saving a boat load of cash to deploy if the bottom falls out of the market. See: The Art Of The Interview

Second, I wanted to see if I could still return to the industry I left behind so long ago. It looks like I can, but at a lower tier firm. However, I also discovered there are several people at my old firm who stayed behind while I went off and did my own thing.

They observed how I was able to negotiate a severance package to be free, and now they aren't very complimentary about my return, even if it isn't with them. What they don't realize is that their disdain is exactly what I needed to help keep me free.

Finally, when you step up to the edge, you realize how jagged and disastrous things can be down below. I told myself worst case scenario, if I did go back to work, I'd gut it out for one year to see what their bonus structure was like, and then leave.

Appreciation Rises When You Get Close to The Edge

Whatever we love, we end up always taking it for granted. Relationships take work, marriages especially. Good health can often be forgotten until we catch a cold.

Financial independence is the same way until we actually go through the cathartic process of facing our worst fear of going back to work for someone else.

Although I was still in the running for this particular job, I sent my prospective boss a cordial e-mail that I would be pursuing different opportunities. I told him to keep in touch if things don't work out with whoever he does end up hiring.

And boy, did it feel amazing once I pressed send! I had escaped the allure of money because this job would have paid $350,000 – $500,000 a year.

Quitting More Money Temptation

It's funny, because we had touched base two years ago when he was looking for someone to fill this role, but we never got very far. I was still committed to putting in three years into my entrepreneurial endeavors before ever considering going back to work. He ended up going with someone else back then, and now here he was trying to refill the same vacancy for the past several months.

I've now got a renewed appreciation for financial independence after going through this latest job hunt process. Writing my 2015 year in review gave me the confidence to continue doing my own thing for a fourth consecutive year. I really appreciate being able to control my schedule.

The ability to hang out only with people I like cannot be overemphasized. This is one of the best benefits of early retirement. So much about getting ahead at work is playing nice with people you don't entirely respect.

If you find yourself taking something you hold dear for granted, please go to the very edge and see what awaits if you take another step. You might have to actually fall to really appreciate what you have. Thankfully, my imagination is still quite vibrant to understand how unhappy I'd be going back to an industry I tried very hard to escape.

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Learn how to negotiate a severance

Learn how to negate a severance with my book, How To Engineer Your Layoff. Walk away from a job you dislike with money in your pocket. A severance was my catalyst to get close to the edge and then take a leap of faith when I was 34 in 2012. I've never looked back.

Never quit. Get laid. Severance negotiation.

About The Author

39 thoughts on “Step As Close To The Edge As Possible To Love Your Life More”

  1. No offense, but if your attitude is to “gut it out for one year” and collect a fat bonus check, they were probably right not to hire you. They’re generally looking for lifers.

    1. No offense at all. Of course I didn’t give the impression that I would just hang out for one year. If you look at my track record, it is a long one w/ 11 years at my previous firm, and 7 years with FS. I just told myself worst case scenario I’d give it a go for one year and then bounce. To leave before then would be a waste of everybody else’s time.

      How long have you been with your employer?

  2. Exactly. I remember my very overweight high school track coach say the same thing. “Run until you puke! That’s the only way you’ll know how far you can go.”

    The first week I puked my brains out! So fun. It made me a better 200M runner, and tennis player. Gosh… 200M sprinting is brutal now that I think about it.

    Not me in the picture. But mentally me during the holidays :)

    1. Puke Power! This is how I know P90x is good for me! Every time I complete a workout, I’m on the verge of losing my lunch.

      Glad that’s not you in the picture! Falling off something like that would not be good for the future of the Financial Samurai blog.


    Sam, I have been reading your blog on and off. My last gig was Software Architect in an multi-national financial institution. I too engineered my severance package but nowhere your package :).

    While I understand there are valid reason to go back to work since it’s much cheaper, for example, to get hired at a Satellite company as an Software Architect than creating a Satellite company myself. But going back to trading time for money not because of cash flow, but just for money? I really don’t get it.

    1. Congrats! Negotiating a severance is ALWAYS better than walking away empty handed by quitting.

      It’s not about the money. It’s about the camaraderie. It’s fun doing something you like with people who also like what they are doing.

      Finally, you don’t really know HOW MUCH it isn’t about the money until you are offered XYZ amount of money. It’s like people who think they have a high risk tolerance and then freak out when their portfolios go down 20%. You don’t know until you face it.

  4. Good for you Sam. It’s so important to push yourself and keep growing. Coming from your background, you obviously need to push the envelope a little further to still feel like you’re making progress (i.e. jobs paying 1/2 million/year!). But, it’s so awesome that you have the freedom to choose, and that you can use the alternative to appreciate what you already have now. Have fun exploring! :)

  5. Back in the dot com boom, there was a lot of debate about going on interviews even if there was zero chance you’d take the job. For high performers, the interviews were good practice. It’s better to get used to the environment, the questions, etc. at lower stakes than wait until a higher staked meeting. Lower performers would get angry at the higher performers for “taking their spots.” Even if you didn’t take the job (or that you stopped the process), it’s still great practice.

    As for the folks who are upset at you and your severance, they can go pound sand. :)

    1. Hah! Yeah. The old office manager whom I butted heads with is now at this hedge fund. Weird guy. Could never look you right in the eye when speaking. His tennis club hosts a pro tennis tournament every year I go to in Marin County. Always a little awkward to see him, but fun too b/c he reminds me of the life I no longer need to lead.

  6. Sam, I cannot imagine going back to work a second after I don’t have too anymore. And if my company offered severance packages ever I would be trying to get one of those asap. Good for you though willing to even consider going back.

  7. Great job sticking to your guns and listening to your gut. I like yourself am easily lured by money too, but in the end, you knew what to do and that is super. You are in a position with options, you worked hard to get to that point so awesome that leveraged it as much as possible.

    I did a similar thing during my sabbatical, I had several very promising consultant opportunities that was a lot of money compared to my employee job – it was tempting but I decided to not even entertain it all..I knew if I looked at it, met the team, there was greater chance of being sucked into something that I wasn’t happy with and I really hate wasting peoples time in the process if I knew all along there was a slim chance I would take it.

    Since then, I listened to my gut more and recently took on a project that was a ‘yes’ for me which wasn’t comparable in income but much more challenging (completely different). I felt that was a personal win because I truly looked at the work/challenges over money (and the money ended up being similar after I took on the job and showed my value as a consultant).

    My insight for your readers is to look at what you want in life, in your career, your personal development, health, relationships and family life and match that with what you do day to day…check if they are aligned or getting you closer to your vision and leverage your superpower – money is no longer a very important consideration in doing the stuff you truly want to do:)

  8. Interviewing is definitely a skill, and like most skills, it fades quickly if you don’t exercise it.

    Whenever I think I’ll be looking for a new job, Google is the first place I call. I wouldn’t want to work there – ignoring their participation in Apple’s wage suppression antitrust activities, they’re too large, too engineering-focused for my taste – but they’re great practice interviews with very smart people who ask challenging questions.

    That said, I can’t imagine putting myself through a grueling interview process knowing I’m going to stay self-employed. It’s like an ex-con locking himself in a cage once a year to appreciate his freedom.

    Freedom is a feeling that lasts forever.

    1. That’s the thing. You never know 100% for sure about anything unless you walk up to the edge and find yourself facing a potential new reality.

      Once you have a lot of freedom, you don’t appreciate it as much. It’s been a great four years so far, but who knows the future.

  9. One of the principle tenets of stoicism is the process of enduring hardship in order to better appreciate what you have. Sometimes, it’s easy to get complacent living a comfortable life without much adversity. Challenging yourself, even with self-inflicted or “pretend” adversity, is an important part of growth.

  10. SavvyFinancialLatina

    Interviewing is an art. Practice is extremely important. I’m not surprised you chose not to go back.

  11. It was interesting to hear you comments on the attitude of former co-workers (at your old place of employment).

    This seems to jibe with my corporate job. Here, we often see people leave for greener pastures and eventually return after they realize that the grass isn’t necessarily greener. However, this is much less likely if the former employee played hardball, either with severance or with an attempt to ‘match’ a new employment offer. Hiring managers / HR know this and assume that the employee is not as likely to stick around.

    1. Yes, there was definitely a certain amount of envy when I left. I knew for a fact that two of my ex-colleagues went to HR and their managers asking for a “similar severance package like Sam.” They were shot down, and were pretty bitter. One finally left on his own accord with nothing, but at least found a good new job.

      I was exuberant and inexperienced back in 2012 wrt severance negotiations. So of course, when I couldn’t help keep my excitement in check. I never shared details of the severance b/c that isn’t kosher, but I assume people figured out a range.

      If I had to work 12 months and make LESS than someone who worked for 2 months and made more due to a severance, I wouldn’t be happy either.

      The lesson is to KEEP QUIET during departure!

  12. I’m wondering what kind of idiot would go back to work when his passive income surpasses his living expenses by at least 50%. :)

    Seriously, kudos to you for pushing the limits and forcing yourself not to take financial freedom for granted. It’s an extreme way to do it, but if it works for you then bravo.

    Just a comment on one thing you said in particular:

    “It’s hard to interview well without practice. I’ve been out of practice for almost four years now, so I figured at the very least, I could brush off the cobwebs. When opportunities arise, it’s all about being prepared. It’s kind of like saving a boat load of cash to deploy if the bottom falls out of the market.”

    This is SO TRUE!!! And most people do nothing about it…

    I have interviewed countless people who have put zero preparation into the interview. Do you know how I know that they didn’t prepare? IT SHOWS!!!

    I always say that an interview is a test you can prepare for. The fact that so many people don’t prepare is mind-boggling to me.

    1. Thanks man. Yeah, interviewing well is definitely a skill that needs practicing. The preparation, the knowledge required to insure yourself the ability to speak conversationally about a complicated topic, the skill to connect with someone different from you when you need to take a piss… it all takes work!

      Interviewing is like acting. The better the actor, the more natural things seem. You can always be 100% yourself.

      The more I interviewed these 11 folks, the more I caught myself bullshitting about things I didn’t care about. It was a good soul searching exercise.

      1. FS,

        Perhaps you could write a post about how to practice interviewing? Obviously interviewing would be the best practice, but in some cases it might not be practical.

        My own personal situation is that I’m in the military. I’ll be in for the next ~3.5 years and I’m sure that my interviewing skills will be rusty at that point. I’m sure I’ll think more about how to work on my interviewing skills over that time frame but maybe it would make a decent blog post?


  13. Did you know going into that grueling interview that you were going to say “no thanks” at the end? Or did you decide only after the fact? Just wondering.

    1. What I failed to mention in the post, which has now been added, is that this job would pay $300,000 – $500,000 a year. So when any employer who is willing to pay this type of money, it’s worth exploring to see whether there would be a good fit.

      I’ve always struggled with escaping the allure of money. So this was a personal win for to walk away and stand strong.

      1. Wow, that is certainly a tempting amount of money. Good for you for giving it a shot and ultimately going with your gut!

  14. It sounds like you made the right choice. Why subject yourself to that level of unhappiness again, Sam? And you’re doing really well as an entrepreneur. I suspect your expectations of yourself are much higher than most people :)

    1. Largely because of complacency. I get a little restless after a while and like to shake things up. Also, I’ve found I never know exactly how far I’m willing to go, or how committed I really am until I’m truly tested. You?

  15. Interested in an update on Uber income now that they’ve cut fees for drivers again. Is it still bringing in any income?

  16. I have to say you have a very interesting take on FREEDOM to test yourself to see if you would really go back to your old employment! I announced my early retirement a couple of weeks ago and can’t imagine EVER wanting to go back to an interview. Good that it made you stronger in your resolve to stay FREE!

  17. I clearly remember interviewing for a job while I was in the process of leaving my full time job about a year and a half ago. My gut told me it wasn’t the right job for me because its niche was exactly what I was trying to escape. But I liked that it was a small firm, they had an amazing office, and the people were great. It was a long interview process – not as crazy as yours – but I think I met with gosh at least 10 people over the course of six weeks. Each interview was between 45-60 minutes as well so it took a lot of time.

    Towards the end I found out I was one of two final candidates. It felt great to be sought after but I felt like I was overselling myself because deep down my gut told me I didn’t want the job. The voice inside my head was saying, “you’re leaving your job to go to this?!” But the money was alluring and it would have paid significantly more than the role I was leaving. I love earning money so the idea of suddenly making a lot more money was tempting.

    But the final straw on my side was new potential boss – she was a 150% type A, no nonsense, single woman entirely dedicated to work and no play, and incredibly intense. The EXACT OPPOSITE of the boss I’d had for 10 years, whom I really got along with. In my final interview, which was with her, I really tried to do my best, but I think my inner doubt crept through. I remember hesitating on one of the questions she asked me about how we’d work together or dedication or something and she probably could sense that. The other final candidate was also younger than me and probably much more eager to kiss up to her and such. Anyway, I didn’t end up getting the job and was so incredibly relieved when I got the call from her that I screamed with glee after I hung up the phone. LOL

    So I understand a lot of the feelings you wrote about in your experience. Deep down your gut knew it wasn’t the job for you, yet there were aspects of it that were tempting enough to pursue it. I think you are better off without that job and know you will continue to flourish on FS with the freedom to write about whatever you want. You’re incredibly skilled at what you do. Keep it up!

    1. “you’re leaving your job to go to this?!”


      When you start faking your interest more and more during the interview, you’ve got to listen to your gut and realize it’s just NOT what you want to do.

      Thanks for sharing! I’d be scared of your boss too. Doesn’t sound balanced AT ALL!

    2. Financial Slacker

      Over the years, I have learned that when my gut tells me “no” I listen. Whether it’s a job I’m interviewing for or I’m interviewing someone to work for me, the “no” voice has always been right.

      However, while my “no” voice is always right, my “yes” voice is not as accurate. I can sometimes convince myself that a certain job or candidate is the right one, when in reality it’s not. I usually go in wanting something to work out, so it’s not a surprise that I’m biased this way.

      So my recommendation, if your gut says “no” listen to it. If your gut says “yes” do more research before you move forward.


      1. Sam, great article
        and Financial Slacker, great post. I am going to keep this in mind while i judge what my gut says

    3. Adam @

      Sounds like the right decision. During interviews I always assume any bad gut feelings are worth listening to, particularly with whoever will be your new boss.

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