The Antidote to Every Entrepreneur's Feelings of Self Doubt

Last Updated Oct 13, 2011 4:58 PM EDT

If you are not scared that everything you are doing is stupid then you are not doing a startup.

But once you get to that point -- of self-doubt and panic and obsessive worry that everything you are doing will be useless -- you also need a way to cope with those feelings.

The way I cope with those feelings is I redirect. I tell myself to think of something else. I remind myself that I grow mentally bored when I do not have a company that I'm working on.

If that doesn't work, I tell myself, what else am I going to do? Get a job?

Most of the time, that's enough. I go through, in my head, how terrible I have been at working for other people. I have heard people say that you can tell you're an entrepreneur if you have been fired from a million jobs. This is because it's so much nicer to work for someone else than it is to work for yourself, so anyone who could do it would do it. Every entrepreneur has thought of this -- the luxury of having a boss who internalizes the problems you leave at the office when you go home at night. And the luxury of having a paycheck every week even if you accomplished nothing for the last month.

Most days, when I am trying to figure out how to cope with obsessive startup worry, I move quickly past the idea of getting a job. I'll tell myself I'll send out resumes, but then the idea of spending time interviewing instead of doing my company is too disturbing, so the idea of working for someone else passes.

I'm on my fourth startup right now, though. And for the most part, being an entrepreneur has been the process of assessing risk -- in my life and in markets. So of course there have been times, over the course of founding all those companies, when I have said to myself that I need a little break and I took that break in corporate America.

It's not a terrible idea. Taking a corporate job for a few months, or maybe a year, can give you more financial ramp-up time to get the company off the ground without you starving along the way. The times my company has run out of money have been some of the hardest in my life. It's so common for startups and it's so terrible when it happens.

Working for someone else can also be a nice break mentally and emotionally because when you have a job, you go there every day, hang out with co-workers, do what you're told, and get a feeling of accomplishment from doing what you're told. It's such a nice equation and one that can bolster you and give you emotional energy to make it on your own.

The problem is that it's difficult to get a job in this circumstance, and you don't want to have to spend a lot of time doing it.

Here are tricks to making yourself look more employable.

1. Focus your resume on times you've worked for other people.
You can give yourself a lower title for when you worked at your own companies, and the hiring manager will infer that you worked for someone else. And you might consider leaving off some of your weakest startups if it allows the times you worked for other people to shine through more.

2. Get rid of your ego. You are already a huge risk because people who work for themselves are generally impossible to manage. The more you can show that you are humble and open to other peoples' ideas, the more likely they will think you're manageable.

3. Tell the interviewer you are sick of working for yourself. It's fine to say you need a break from the pressure. But say it like, "I miss being part of a team" and "Sometimes it's nice to work on someone else's vision for a while" -- these are lines that make people think you genuinely want to work at someone else's company.

4. Make the interviewer identify with you. Most people wish they could work for themselves. If you tell the interviewer you thought you could do it, but right now it's just too much tumult in your life, or something like that, then you are appealing to the very feelings that the interviewer has about working for himself. So he will not only understand, but also feel like you are like him.

5. Make sure you are good to the company. If you get the job, don't leave four weeks later. It's not nice. Try to stick it out long enough for you to get what you want -- rest, money or both -- but also long enough for the company to benefit. They took a risk on you. Do something significant for them on the project you were hired for before you decide to go back full time to your company.

The side benefit to taking a day job is that it's a great way to know if you really should be doing a startup. If you continue working on your company while you have this day job, then you know the startup is right for you.

Flickr photo courtesy of B Rosen, CC 2.0

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