Ask HN: Late twenties, last four years spent fiddling w/projects. Employability? | Hacker News Reader

Ask HN: Late twenties, last four years spent fiddling w/projects. Employability?

19 pointstastyface15 comments

Hi HN! I'm a 29-year-old programmer who left my SV job four-odd years ago to pursue a life of travel and indie development (at least until my savings ran out). Travel-wise, things have just been peachy. Career-wise, I've accomplished a whole lot compared to what I was doing before, including developing a bunch of small/medium-sized native iOS and OSX apps (one of which grossed $10k+), publishing a (simple == sub 1k line) open source project that has close to a thousand stars, blogging about technical topics (nothing too fancy), and implementing/blogging a very interesting CS research paper. If I play my cards right, I have maybe 1-2 years of independent living left, assuming I don't get another "hit".

Still, I am filled with dread. By my own evaluation, my progress has slow, and I feel like I could have accomplished 2-3x as much during my "sabbatical" if only I spent a bit less time procrastinating and forced myself into unfamiliar programming territory. (I perceive this as having wasted about 2-2.5 whole years out of this period.) I have a recurring, deep-seated fear that if my cash runs out and I have to re-enter the job market, I'll simply find myself unemployable. Although I'm almost 30, I don't really view myself as a senior engineer material; I can implement stuff just fine if given a blueprint, but my experience with high-level architectures and complicated, stateful systems is lacking. (Working on getting better at this, though. Lots of projects in the pipeline.) I also have zero managerial experience since I've been entirely working by myself. On the plus side, I have a CS degree from an excellent university, though I imagine the importance of this wanes as you get older.

HN, are my fears justified? Am I just falling into a bottomless pit, career-wise? Or is this stuff correctable?

No, should you ever want a job again, on your CV put that time down as a company of your own creation and list it like you would any other job. What you made, what you achieved, etc. I did this about 4/5 years back, didn't have any problems getting interviews.

When you start getting interviewed they'll ask why you're leaving self-employment and all you have to say is you tried running your own business, it didn't work out, and you want the stability of a full-time job again. That'll be about the extent of it.

References are a little trickier, I had some consulting clients that I'd done part-time work with, so had people to ask. To be honest, references are at the "we want you" stage so they're a bit more flexible.

The ultimate problem I found was being an employee is frustrating so I left full time again and switched to consulting instead.

The only thing that you mentioned that would make me a little bit nervous is that you have been working entirely by yourself.

I would think a github repo with 1000 stars would give you the opportunity to work with others. Maybe start accepting some pull requests, or join another open source project.

Otherwise, everything else that you mentioned seems like pretty run of the mill imposters syndrome. You built some products, and real users ended up using these products. That seems like some pretty solid experience right there.

I would also think about how you present yourself. Some things to consider:

1. Would you want a contract gig or a salary position. If later, be sure to make sure you don’t sound like a drifter. Employers don’t want to invest time in someone that doesn’t plan to stay around at least a little while. 2. Can you do some contract gigs now to keep up skills and resume? 3. As for developing your own “hit”, I think the idea is more important than the tech stack

Keep doing it - just take on some contracting work to extend your runway. ios contracting work should be really easy to find.

Don’t give up now. The risk is good for you. Use it to “light a fire under your ass,” as the saying goes.

Be selective about opportunities and don’t underestimate the advantage of your position. Many people spend years employed dreaming about the sort of independence you’ve achieved.

What was your programming level when you left the job and started working on these projects?

I view myself as probably a 4/10 at this point, really never having built a super complex application from start to finish. And that's the fear holding me back. However I feel it would light a big fire under me to improve in a lot of ways, be super efficient with my time, study hard and put it into practice. Any advice about this "imposter syndrome" feeling would be appreciated.

Your employability is also going to be dependent on if you're willing to relocate and what you are willing to accept for a salary. I think you should land fine as long as you've got decent "emotional intelligence"/teamwork/sociability skills and you are willing to accept starting off at place that isn't necessarily perfect for you, but good enough.

Experience is what it all boils down to, and it sounds like you've got nice set of experiences to draw from which might set you apart from other candidates.

Maybe obvious, but so much seems to be a confluence of factors beyond your control and ones within your control. Luck plus making the right connection at the right time would help. Also doing well in an interview is a no brainer. Could you make another indie app & gross more money and live cheaply? Bosses kinda suck imo (but maybe might be cool sometimes for a while) so running my own show is always an appealing possibility.

Firstly your experience is very good, and it must be very enriching. Do not undersell yourself, you can give a very positive spin on your indie experience. You can cite this as your entrepreneurial foray.

Secondly, why not try for few interviews at good companies, and see how you like the feel - You might like it - If it does not work out well, you can always go back.

It seems to me that your fears are unjustified. Being unemployable as a senior, architect level developer is very different from being unemployable as a developer, period. It seems to me that you have the skills and resume to find a senior role that is not that senior as architect or CTO. Or at least a more junior one with real fast growth.

Off-topic, but I've been thinking about doing my own sabbatical in order to focus on my own projects and hopefully start a business. Can you share anything about what you did to get started? How much money you had saved? How did you adjust your life?

Not OP, but I did this and it really depends on what you want.

I had some success, then got obsessed with AI. After 1-2 years studying nonstop figuring out what to build I ran out of money and had to consult.

I would have made more money working full time... but perhaps not if my next project goes well.

That said, even with what I know now, I'm about to do it all again. The freedom is priceless.

Risk is scary. But going 9-5 to a job hoping for raises, good bosses, and stock liquidation events is even scarier IMO.

My main adjustment was to (mentally) let go of all my inessential belongings. Pretty much all my important things now fit in a small, maximum-legal-carryon-sized suitcase, along with a small backpack and the stuff that I wear on my body. This lets me live and travel loosely, whether hopping between Airbnbs in Europe or lucking into enticing month-long sublets back home in SF. If I get tired of my surroundings, I can pick up my life and move somewhere else in the course of a day. It's extremely liberating, both physically and mentally. (Of course, this presupposes that you don't have an SO or dependents.)

It took me a while to figure out my optimal "toolkit". Productivity-wise, my essentials are a Roost dock, Logitech wireless keyboard, and Logitech wireless gaming mouse. Working from cafés is really great now. (And my shoulder pain is gone!)

Productive travel advice: don't do hostels. Airbnbs are awesome, but only pick ones with private rooms that have a nice desk and chair. It's way more convenient than spending extra money on a coworking space (unless that's your thing). If you're planning to actually get work done, stay in a given city for at least two weeks, and preferably more than a month. Traveling to a new city always takes some adjustment.

I started with $100,000, but that's way more than you need. (I just didn't have very many expenses over the course of my SV career.) When I was Airbnb-traveling in Europe, I think I spent about $30,000-$35,000 a year when all was said and done. This was very comfortable living in Western Europe though, and I probably spent about half to two-thirds of my time eating out. You can definitely do $20,000 or less a year, especially if you visit cheaper countries, sublet places for at least a month, and cook for yourself more.

If you have more than, say, $10k in savings, put some of it in FDIC-insured accounts with ~1% returns (e.g. Ally), and invest some of it index funds (Vanguard). It's basically free money unless you happen to invest right before a major recession.

You're not unemployable and don't underestimate the value of your experiences over the last four years.

I feel you bro...

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