The Job Experience, StartupVille: Year #8

Another Job Search


So I find myself writing, yet again, a page about the job search itself.

This is because I want to share some of the changes in approach.  I have no doubt that these adjustments helped me to land a better fitting position this time around.

  • I took my time and did phone interviews for over thirty places.  (It helped that I was a) out of work and b) the employment market in my area was fairly good — I had plenty of time to devote to the search, and lots of opportunities to sort through.)
  • Once I’d narrowed things down a bit, I went on-site to five different companies to talk things over in person.
  • I had a specific position in mind this time:  I wanted to leverage the skills I’d built up so that I didn’t have to do nearly as much learning to get up to speed on the job.  And I liked technical work so my focus was on contributor-level positions.
  • I didn’t place an emphasis on salary or benefits and instead focused on how I seemed to feel about the prospective company’s culture, employees, and management team.

Privately I felt like:  OK.  I have a net worth of 250K.  This is a pretty good pile of seed money for FI.  I don’t need to work as hard just to make a bit more income at this point.  Instead I’ll concentrate on creating a decent, balanced life.

After all, the first couple hundred thousand are the hardest to make.  I thought: From here, the power of compounded growth should take hold of my stash and do much of the remaining work on my behalf.  If it takes me a couple of extra years to reach FI, so be it.  I don’t want to be a careerist workaholic anymore. 

Put another way, it was time for me to trade a bit of potential money, in the form of salary and benefits, for more time away from the office.  I just had to make sure I found a job that would allow me that flexibility.

There’s More to FU Money Than FU

The standard definition of FU Money is that it allows you to walk away from a job that has become intolerable.  You don’t have to stay any longer than you want; it turns the employment-at-will equation into a two player game instead of a rigged one where your company holds all of the cards.

But there’s more to it than that.  Having a stash built up doesn’t just let you say goodbye to your old, crappy employer.  It also helps you to take your time picking the new one, so you can do it right and get a better fit for yourself.

This was important to me at the time because, as you can imagine, I was concerned about winding up at another FinancialCompany.

To prevent this, I asked a lot of questions about work-life balance during my face to face interviews.

I’m perfectly aware that many other bloggers and more corporate-y job-hunting sites recommend that you do not broach this subject with any prospective employer under any circumstances.  I’ll list just a few examples, from the FinancialPost, BusinessNewsDaily, and Forbes.

The argument goes:  If you really need the job, then revealing that you don’t want to work more than 40 hours a week places you in a position of weakness, relative to your competition.  They’d much prefer to hire the guy or gal that doesn’t seem to mind unpaid overtime and working at odd hours.  The simple act of asking the question makes you sound lazy, like you’re already scheming your way to doing as little as possible — before even landing the gig.

The thing is, if you have enough money to live for several years without working , then you don’t really need the job — you merely want one.  This fact completely invalidates all of that advice about not asking too many questions on this subject.  You, with the pile of gold coins in your vault, can afford to take some chances by probing a little deeper into the culture of any particular company if you so choose, and you can do all of this risk-free.  In fact, I would argue the greater risk is selecting another bad-fit job; you don’t want to invoke the power of your FU money again — it’s not to be used lightly.

That being said, some questions are more tactful than others when you’re trying to dig up the truth about your prospective employer’s culture.

A few I found effective:

  • Tell me about how projects are planned and deadline estimates are generated. What is the process?  (If there’s no process in place, chances are good that it’s unfettered chaos.)
    • Follow up questions:  How often does this system work, i.e. is it common for projects to exceed deadlines?  What happens when dates or budgets are missed? 
  • Do priorities for contributors frequently change?  
    • If the answer is yes, it can be a sign of dysfunction, which usually leads to overwork and stress.
  • In the job posting, it mentions flex schedules.  Can you elaborate on what this means?  
    • Here, you’re asking about work-life balance without asking about work-life balance.
  • Please describe a typical work week for the person who fills this position.
    • This will often lead your interviewer to mention times of day in their response.
  • What are your favorite and least favorite things about the company culture? 
    • Another open-ended question that will often result in some elaboration about working conditions.

If you want to be even more careful, you might want to restrict these questions to non-managers.  They’re typically more candid when it comes to discussing work-life balance.

Personally, I was fairly aggressive and blunt on this topic.  Of course, I’d bring up other subjects first (questions about technical responsibilities and other job-related functions) to illustrate genuine interest in the role and the company.  But I made it a point to not leave an interview without doing a fair bit of investigation in this area.  I even asked questions like “What percentage of my week, on average, do you anticipate I’ll be in meetings?”  One place said “About half,” which prompted an accidental laugh during the interview. Pass.

The absolute truth is that when I received warning signs that employees were overworked, those signals meant that I didn’t want the job anyway, and therefore I didn’t care all that much if the interviewer was put off by my question or discerned that I had a “lazy attitude.”  Instead, I figured,  If you’re bothered by the fact that I don’t want to work a lot of mandatory unpaid overtime, that’s fine — I’m glad we’ve identified up front that this isn’t going to be a good fit.  Good luck with your search.

And two of the five places were put off.  But the ones that weren’t — well, I was able to more confidently pursue those opportunities as viable options.

As I mentioned, I went in for interviews with five different software companies.  One of them in particular felt exactly like FinancialCompany.  (I couldn’t get out of their building fast enough — I could almost tangibly smell the sense of overwork, panic and desperation seeping out of the pores on their skin.  Blarg!)

But I won’t get too bogged down in details on this subject.  For the most part, they were just interviews.  I went in to learn about the company, and in turn, they learned something about me.

At the end of this process, I ended up at a software startup in the Boston area in the United States.   The exact location was about 40 miles away from my apartment, so I moved to a new place about 3 miles away from the office building and started in on Year 8.

I selected this place, which I’ll call StartupVille, mostly because I liked the manager of engineering, whom I’d be reporting to. We spoke for close to three hours and I felt like we had an understanding.  He answered my questions about work life balance and company culture in stride, and he seemed to be genuinely fond of “his guys.”



Salary 105K
Employer 401(k) Contribution None
Sick/Vac 20 day pool
 Total 105K

Note:  One of the companies offered me 130K plus 25% discretionary bonus and 6% 401(k) match, for a potential total of 160K+   I passed on it anyway — answers to interview questions about balance were alarming and the signals I was getting from employees were all wrong — it was clearly a sweatshop, and I’d be doing a lot of management work again.  I realize that extra money would have shortened my journey to FIRE but I couldn’t fathom jumping right back to 60 hour workweeks — at the time, it seemed like nothing could be worth that extra money.

Instead I simply took this as a datapoint, that I probably could make 150+ at another job if I ever wanted to speed things up again.

But I haven’t – and I think I’ve been much happier for it.

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7 Responses to The Job Experience, StartupVille: Year #8

  1. Tom says:

    I’m almost embarrassed to admit that I’ve had jobs where my whole life revolved around work with little time for anything else – for extended periods of time. Years… I use to envy people with 9-5 jobs who never had to take work home with them. As you noted, work is so much more tolerable, and dare I say, even enjoyable, when you can assign it sufficient energy but with remaining stores in the battery packs for other things. Money is nice but when you don’t need much you have to question your motivation. You figured that out much earlier than I did.

    Over two years ago I turned down a contract gig that would have required a horrendous hour plus commute in both directions. Having FU money, I turned it down and two weeks later was offered a better position for more money and an apartment with less than a five minute walk to work. I know two other guys who were not as financially secure and to this day are still making that two-hour commute. Though they didn’t complain all that much, to me, at least, I could see them aging in front of me. The world will be a better place when we greatly reduce the need to sit in traffic for hours each week to earn a paycheck.

    • livingafi says:

      I really love the stories like this. Not the part where you were overworked, of course, but rather the fact that your stash allowed you to carefully consider your employment options and ultimately gave you a huge boost in life-quality in the form of not having to commute. Aside from the fact that long daily drives simply cost a lot, they’re draining and often feel like half of the work you do, on any given day. Lots of co-workers throughout the years have said their commute is the #1 thing preventing them from exercising on a more regular basis, for example, and it makes sense — that hour and a half on the road would be the perfect time to dump into a trip to the gym or even a long walk around their neighborhood. Thanks for sharing.

  2. Frankie's Girl says:

    I haven’t been a good commentator, but I just wanted to say that this series has been FASCINATING to me. I actually check in every day or so just to see if you’ve written more about your working life, so the length of the posts have been a bonus as far as I’m concerned. Awesome reading!

    • livingafi says:

      No worries, I’m still working on the next one. For what it’s worth, they take me a while to put together, mostly because of the length and image work. Not complaining at all — actually I find the process very enjoyable — but trying to offer an explanation on the number of days between posts. It’ll definitely be out in another day, two tops. There goes my regular job, getting in the way of my hobbies yet again… BTW, thanks for the comment and I’m glad you’re not bothered by the word count.

  3. Sounds like some good opportunities out east! Is the demand for engineers as hot as it is here in SF you think? The job market here seems to make people want to move every 2-3 years.


    • livingafi says:

      Thanks for stopping by, Sam. So I’m not familiar exactly with how hot things are in SF, but definitely it’s cooking along the NE corridor right now, and has been at least since 2012. For many people, it’s a good time to move and finally get that job-change-payraise that your current employer has been denying you for the past X years.

  4. Frank says:

    This is an excellent story, hell of a read

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