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The Fear of Long Term Failure
Headshot 128 Ben, September 22, 2014

One of the great and initially counter-intuitive features of the tech/startup community is the welcome embrace of failure. Spend 6 months on a product that failed? Pivot. Move on to the next thing. Work on a company for while that fails? Move on to the next one. This is an amazing characteristic of the community because it prevents us from making mistakes brought on by fear of failure. If you're trying to pitch a no-hitter, you can't play tight and aim the ball. You just have to let her rip and hope you've got your good stuff that day. As soon as you're afraid of your next pitch, the ball is going over the fence.


"Freedom is just another word for nothing left to lose"
- Janis Joplin 

But what happens when these year long failures turn into 5-10 years? Piece by piece, year by year, it gets a little harder to embrace failure. What if I have 10 failures that take me a year each? Am I going to completely waste a decade of my life on these successive failures? If I had gone to Google or Facebook or worked toward partnership at a big professional services firm, where would I be after 10 years of effort? What kind of salary would I be making?

These questions usually get left out of the "failure is a good thing" conversation, but they sure feel capable of striking the panic-inducing fear into people that can be tough to handle.

I've felt this fear acutely at times over the past several years, but I've also found a couple of remedies for it.


1. Do things that are cumulative

I'm doing this right now. New and valuable skills, blog content, and open source code are all examples of things that, even in the face of a singular failure, can still be really valuable for you and your career. A new website or app might be a massive failure, but maybe you learned some new coding skills or a new piece of technology that can be a valuable asset in other jobs or future product efforts. A certain gig might not work out, but the following you built up with your blog content or open source efforts could turn into a huge asset the next time you're looking for work.

On their own, none of these things is going to make you a millionaire or turn you into some business mogul. However, building a couple of these over time, little by little, can result in some valuable assets that you could parlay into customers or work down the road. It also provides you with a mental hedge: no, I didn't just waste 5 years -- I built some hugely valuable skills and assets.


2. Meet more people

The longer I exist in a professional setting, the more I buy into the value of personal relationships. When I look back at my short list of formative career events, none of them are centered around some amazing piece of code I wrote or some Herculean effort on a project. They're pretty much all driven by some personal relationship I have and something that grew out of it. I think we'd all agree that the more people you know, the more people there are going to be to help you out along the way.

The other side of this coin is helping other people. I think offering to help someone first is an easy way to initiate a relationship and it gives a positive first impression. If any number of those favors never get reciprocated, that's perfectly fine. But some will. And we're playing the long game here, not the "milk my relationships for all they're worth in a day" game.


3. Embrace the feelings that led you here in the first place

This idea is the least tactical and practical of the bunch, but it's the most helpful in a moment of panic. In the past couple years, I've thought the words "what the hell am I doing with my life?" more times than I can count (and probably said them out loud plenty of times as well). Every time I do, I try to consider the alternatives to what I've been doing. What if I stayed in a big corporation 9-5 for 50 years? I'd get up, go to work, go home, go to bed, and I'd do it for FIFTY years (I'm being dramatic -- indulge me). The thought of doing that for 50 years is 1000 times more terrifying to me than not having a real answer to what I'm doing with my life.

After I run through this scenario in my head, it's a lot easier to get excited about what I am doing. Whether or not I want to accept it at the moment, there were some very calculated choices that led me here. I love having freedom and control over my time, the nature of my work, and where I do it. I love getting to work in a fun environment where we don't really have to deal with the maddening red tape of a big company. And I love the fact that our company (shameless plug: FlyoverWorks, check us out) lives and dies on our success or failure in the market -- not whether some random manager likes me and says I did a good job.


If you enjoyed this post or have any thoughts, I'd love to hear from you on Twitter: @bcroesch


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