When should I quit on trying to build my own business?
February 5, 2016 6:49 AM   Subscribe

At what point do you give up on trying to do your own thing? After two failures? When the adrenaline kicks in as soon as you get up?

I'm 35 years old, a doctorate computer scientist by trade. I started working at about 30, where I took a job in an academic department earning about 50% of my industrial rate on the basis that it provides me with the freedom and platform to do entrepreneurial things.

Over the last 5 years, in addition to doing my daytime job, I have done a lot of contract work in the evenings to build up a base of money for investments in two companies, one of which failed and one of which is shakily running along with no indication of whether it will fail or succeed longer term (right now it's tending towards failure). I am non-operational in the company as my role is now redundant, though I maintain my shareholding.

The cost of this has been immense to me personally. I feel like I've had 2 full-time jobs at any given point. In addition, I've saved nothing apart from a small emergency buffer, trying my best to put my money where my mouth is by investing in the companies I've founded; no house, no marriage, no new things etc. I've had little in the way of holidays, free time or a life, being driven completely by a laser-focus on trying to achieve my goal of building a self-sustaining

Recently (in the last month or so), however, I've been gripped by this feeling of panic and fear. Panic and fear that I will end up with nothing and that I will be unemployable soon (I don't do much technical work outside of the contract work and technical work is beginning to frustrate me because I find it tedious and boring).

While rationally I know this is due to a choice I've made and is not true, I have a whole 30 years ahead of me, I have training from the best school in the UK, I have a reputation that is respected, etc irrationally I feel all is lost.

I've searched in myself about whether I want to go work for an existing company or whether I should try one last time to do something of my own, and, I am conflicted about this. On one hand, I want the pain of uncertainty and stress and worry that I'll ever make it financially to be over, on the other hand when I think of giving up my dream to build a self-sustaining company to work for someone else I feel frustrated and like it would be a failure of a lifelong dream. I feel tired and broken and unable to get back up. This is compounded by people around
me in similar situations who have managed to achieve the same goals as me.

I would really appreciate any advice anyone has, having been in a similar situation, on how they proceeded in similar circumstances as right now I feel I don't have the ability to think about this
logically or straight.

In particular, I'm interested in people from the tech industry telling me how more unemployable I'd be if I went another two years without actually writing code on a daily basis, even though I'd be doing technical and "business" processes (architecture, team leading etc).
posted by gadha to Work & Money (11 answers total) 6 users marked this as a favorite
I can't speak to the specifics of your industry, but I would say that if the quest for success makes you miserable, then maybe you need to rethink what that success would mean. I gave up a life of ambition for a life of comfort, routine and security. While I am very, very happy I did that, it doesn't mean I don't look back at what I used to think I could accomplish and feel a bit sad at what I'm doing now. But rather than let that depress me, I use those feelings to motivate me to do more with my life, rather than stew about what my life could have been. 30 years is a long time to work on other interests, but it's hard to accomplish much when you're miserable.
posted by Mrs. Rattery at 7:10 AM on February 5, 2016 [2 favorites]

Regarding one specific point, when you worry you might be unemployable because you (will) have spent a long time in doing non-programming work, do you worry because you love coding and want to do it for a living? Because project management, program management, and other management/business/consulting jobs are also options to consider. And "learning from failure" is supposed to be a highly spinnable experience.
posted by trig at 7:31 AM on February 5, 2016 [2 favorites]

Response by poster: @trig I worry that my academic/startup experience will not be taken seriously from a project management perspective but I won't be up-to-scratch from a coding perspective. As an individual I enjoy the role of architect/team-lead (inclusive of code contribution with my team) but this doesn't seem to necessarily translate into equivalent positions in industry.
posted by gadha at 7:38 AM on February 5, 2016

*Why* do you want to build your own business? It doesn't seem to have made you happy. Starting a successful software company can involve a lot of luck and things can go poorly due to no direct fault of your own. It's decidedly not for everyone. It also requires skills that not everyone possesses - one can be a brilliant computer scientist and a poor marketer. There's no shame in that. If you do keep trying, perhaps you should look at starting a company with a group of co-founders with complimentary skills?

As to what you could be doing in private industry, I don't know the UK market, but there's plenty of call for skilled software architects, project managers, etc. in my area.

With a PhD, a background in academia, and an interest in new ideas, you might also see if you can find a research position in industry. They're getting harder to get as budgets for R&D get slashed, but I know some very bright people that get paid quite a bit to think up interesting things all day.
posted by Candleman at 8:55 AM on February 5, 2016

I don't know your industry well enough to comment on that front, but I work with lots of small start-ups and have formed three companies myself. The management of emotions is a completely under-appreciated contributor to entrepreneurial success. Put another way, you sound to me like you have a mismatch between your risk appetite (evidence: you have been willing to build your entire life around your entrepreneurial aspirations) and your risk tolerance (evidence: you have discovered that the variation between hopes and outcomes is making you miserable). Without working on that balance, you may never find happiness (let alone success) as an entrepreneur. Fear is the mindkiller.

The "fight or flight" tension you describe is your body telling you that whatever emotional and/or risk management strategies you have in place aren't enough. Vis-a-vis risk management (and setting aside whatever shortcomings there are in your business model), obvious tactics include taking on a partner/outside investor so you're not going it alone, getting a coach so you have some outside perspective and a place to vent, examining whether you have the right people in place, and taking legal steps to shelter your personal assets from your business life.

You may also have based the companies on a business model that doesn't scale efficiently, which is a sign that you're under-capitalized. In any case, your circumstances put you in the worst possible head space right now: you don't have a daily role in the company, but you have substantial resources invested in its success. Moreover, even if you had more control, it's questionable whether you could serve as a leader there given your day job: Not enough time, e.g., another kind of under-capitalization. Plus, your skills may not be what the company needs right now.

Look for counter-intutive things that might help your head space. For me, the first time, it was critical that I rent an office space, even though that raised my monthly costs, because I needed my home to be a place of refuge. Another thing that takes guts but may help is firing/outplacing clients that sap your energy (but nicely). Trust me, they're not worth it, and you can take advantage of the luxury of your steady teaching gig to free yourself from them. The same is true for employees.

Do you really understand why your company is flailing? If so, you didn't say in your question (which is fine), but if you're going to solve this problem you obviously need to know what's not working vis-a-vis product, process, pricing, execution, market, personnel, etc.) If you really want to double down on your company and devote yourself to its success, it may be necessary for you to take a sabbatical from your day job. High risk, high reward. But look deeply inside yourself first. What do you really want, apart from the lifelong dream of building a company? And by the way, you can do it again... maybe the third time is the charm.
posted by carmicha at 8:59 AM on February 5, 2016 [5 favorites]

I wonder if there's an intermediate option. Might taking a "day job" in a startup-y place (but not so new that you're not getting a salary) have a similar upside potential and/or help you learn skills or make contacts that support your next independent venture? Best of both worlds: short term income and security, long term independence?

I'm not in tech, but I suggest this for three reasons. 1. In my field, people who go straight from academia to consulting sometimes lack crucial info on the field. (Not always though.) 2. I believe in heeding the panic you describe, for a lot of reasons. 3. It's not an irreversible decision (I assume?).
posted by salvia at 10:24 AM on February 5, 2016 [1 favorite]

Maybe it's time to sell your company, while it's still operating. A buyer might see potential that you don't see, or your business might be complementary to the buyer's present business. You'd get some cash out and some breathing space for you to consider your next move.
posted by JimN2TAW at 11:07 AM on February 5, 2016

I've searched in myself about whether I want to go work for an existing company or whether I should try one last time to do something of my own, and, I am conflicted about this.
You are only 30. Putting aside your entrepeneurial vision for now does not mean abandoning your life-long dream. Plenty of people start companies in their 40s and 50s - it can be harder in terms of your other life obligations but it happens all the time - especially if you have an idea that is good enough that it can get capitalized.

I'm not sure exactly what your involvement in the start =up companies look like. It sounds like you have day job, that is academic, that pays the rent, evening contract works that creates investment cash and then you also invest money (and in the past time) into start-up ideas. I'm wondering if you are leaping into start-up ideas because you are in love with idea of starting a company not because you have found the idea that will really go places. Also, if you pick your job right, it will give you valuable experience that can help you bring more skills and experience to the table the next time you try doing a start-up.

My advice, plan to take five years off and then wait for the really, really good, too good to pass up idea that makes you excited again.
posted by metahawk at 11:45 AM on February 5, 2016

Another thought:
WHY do you want to do your own thing? To make a fortune? Once you had the money, what would you do with your life? Think seriously about this because you can probably get from here to there far more directly if you know where you really want to go. There are a bunch of retire early blogs (Mr.MoneyMustache is my favorite) that are about how to afford to live the life you love. (Hint: focus on what you really love and not on empty status)

There may other reasons than money, but whatever the end goal is about, know what you really want to get out of it can help you think about better ways to get what you REALLY want.

Plus start-ups are notorious prone to fail. Fortune says 90% of startups fail, although I doubt that is a scientifically sound number, it suggests that if you spend just two years on each failed startup idea, it would take more than a decade (six trials) to have even a 50/50 chance of having a success (where success is defined as not going out of business.) If success requires a return on your investment that equals the stock market, it becomes even less likely. All the more reason to think if there are other options that would get you to your long term goals faster, less harrowing and a higher probablity of success.
posted by metahawk at 12:02 PM on February 5, 2016

As others have said, you really need to very clearly articulate exactly why you want your own company. If you dig down into that, you might find that there are other paths to your actual goal that will work better.

If you answer that and still feel the correct answer is building your own company, consider pivoting. Consider the possibility that you are just missing the mark and an adjustment to your approach may be needed.

It might help to spend some time reading biographies of entrepreneurs. IIRC, Hershey had multiple failed businesses roughly in the sweets industry before Hershey chocolate was born. He kept trying, but each time, it was something different from the last.
posted by Michele in California at 12:50 PM on February 5, 2016

This might be too personal or completely off the mark, in which case I apologize and please feel free to ignore the rest. I recognized your username, though, and it seems like the issues in your question have sort of been running themes for you for years, even before you graduated.

The feeling I get from your questions is that you have the idea that you need to accomplish something impressive to others in order to feel worthwhile, and that you also have an enormous amount of insecurity about yourself compared to others. (I hope your username wasn't chosen in self-deprecation.) (Also, I'm not judging you -- I'm still dealing with the same thing, though it's getting better.)

If all that is true, then I think the most important thing you need to do is to find a way to feel good about and proud of your life even if it turns out you never accomplish a single "impressive" thing.

Partly because things happen that you can't control; partly because you've already done so many impressive things (academics, Google (?) internship, two businesses, long-term relationships, etc.) and yet you don't seem to rate those accomplishments much because there are other people who've done even more, and the truth is that there always will be; and partly (in my opinion) because what a person adds to the world has little to do with the blinginess of their resume or obit.

Anyway, feeling more comfortable with your own self can make the other choices seem less deeply important. A worthwhile person who goes to work at a company for a few years and then reevaluates whether he wants to keep being an employee or try setting up a business again is still a worthwhile person. Same for a person who sets up a third business that ends up failing, or who gets rejected for 50 jobs before he finds a good one, or who decides to get an MBA and find work as a consultant, or who decides to just focus on research or teaching or sysadmin or working with kindergarteners, or who decides not to let himself reject himself for job opportunities before he even applies, or who decides to work to live and not the reverse.

You've done a lot more than most people your age and I think you're underestimating yourself and your value as an employee and as just a plain old person considerably. I hope you find a way for these things to feel less fraught for you.
posted by trig at 4:48 AM on February 6, 2016 [3 favorites]

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