How to Return to the Entrepreneur Path?

by Jason -- September 25, 2013


My ultimate goal is to start a company and work for myself. I’ve tried it once. It was awesome. It wasn’t necessarily successful, but I definitely know that’s the path for me.

The question I’ve been grappling a lot with lately is how do I get there again?

I’m married and we have a daughter. Quitting my job, living off of savings, downgrading our apartment and eating ramen for a few months no longer seems like a viable option.

Here are two seemingly valid excuses…

1. I prefer to spend my “side-project free time” with my wife & daughter.

In the past, my nights & weekends have been focused on side-projects. For the most part that side-project has been Unanchor. Now that we have an Editor that project requires much less work. It’s been great to spend more time with my family.

2. More responsibility than ever in my day job.

I was promoted to CEO a few months ago. It’s exciting, but it also makes it difficult to find time (or should I say prioritize my time) to do things other than the job.

The extra time I spend working at night or during the weekends, I like to catch-up or get ahead for the “day job”, rather than trying to start a new side-project.

This all raises some additional questions:

1. Am I really cut out to be an entrepreneur?

Perhaps I should accept that most people don’t work for themselves and it’s not a bad thing.

2. If I am serious about starting a new company, how do I get there?

Starting Unanchor, we lived off of savings and then Sharon, my wife, worked to support us. In our current situation, I don’t have the luxury of either.

3. Am I really just afraid to fail?


Unfortunately this post doesn’t really have many answers at this point. Hopefully those will come at a later date.

Thanks for reading. It’s therapeutic to write-out my thoughts. If you have challenges, what are they? Writing them out may help :-).

On a related note, I read this post the other day: If you’ve ever wanted to do a startup there is simply no better time than right now.

Be awesome and help us share:

4 Responses to “How to Return to the Entrepreneur Path?”

  1. Hey Jason,

    Congrats on the new daughter (that is a startup in itself)! I empathize with what you are going through.

    Being promoted to CEO is also a big deal - isn’t that pretty entrepreneurial in itself since you are the big boss? Maybe you should ask for more stock so you feel like it is your own company.

  2. Thanks Rishi! I definitely agree that being promoted to CEO feels entrepreneurial. Perhaps it just needs to take some time to sink in. Thanks for the advice!

  3. Hey Jason! Delayed response to this, but I hope you are settling into whatever balance is best for you.

    There’s a difference between starting a company and being entrepreneurial in the way you approach your whole life, I think. In college I started the Santa Clara Entrepreneur Organization, and I always wanted to “be an entrepreneur” and had visions of this perfectly balanced life with passive income streams that allowed me to work and travel anywhere in the world, etc.

    Ok, so I still want that! But I have stopped defining myself as an “entrepreneur” or not, and instead just try to live my life in an entrepreneurial fashion - i.e. not always just doing what everyone else does, and looking for more effective ways to solve my own challenges.

    Though sometimes doing what everyone else does is perfect!

    A friend reminded me recently that it’s critical to “know what you’re playing for.” If you have specific goals for your family that the job provides for, then great! Just make sure that it is sustainable for you (i.e. you won’t burnout and end up hating the job, etc.).

    Good luck, brother! I hope you find whatever path you are looking for =)

  4. And now a delayed response to yours :).

    Thanks Joe — that’s an excellent point. And well timed also, as I’m currently trying to figure out what the next year brings me. Hope all is well dude!

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