Follow Your Heart, Respect Your Situation

I got calls from two separate aspiring entrepreneurs this week.

Their stories are strikingly similar:

  • One is 28. The other is 29.

  • Each has an awesome idea for a startup that he is actively pursuing.

  • Neither are currently working at a company, but both are in late stage interviews at companies.

  • Both are trying to decide as to whether they should take a 9-5 job or exclusively pursue their startup.

And yet, my advice to each of these entrepreneurs was very different.

So, what gives? Why did I point them in two different directions?


There stories were similar. But not the same.

It turns out that one of the new entrepreneurs has six months of runway (amount of time before his savings run out). He’s also got an idea for which he can have a prototype (first version) ready in a few weeks.

Finally, because of his background and industry he’ll easily be able to jump back into a job at the same pay-grade in six months as today.

The second entrepreneur has one month of runway and his prototype will take more like six to eight weeks to have ready.

As well, he’s in a hyper-competitve industry and his last position has set him up well for a nice salary increase that might not be there in six months time.

You can guess which one I encouraged to pursue his startup full time, and which one that I recommend take a job while pursuing his startup on the side.

For the first entrepreneur, taking a job now would really just be the result of fear and over-dependence on comfort.

For the second entrepreneur, not taking a job now would be borderline reckless.

Great entrepreneurs are not afraid of risk, but they are masters of managing it.

Different Recommendations, The Same Destination.

Interestingly, while my recommendation to each was very different, my aim for each is the same:

To get them to take the next step toward launching a successful business.

For the first entrepreneur that means pursuing his startup with abandon.

For the second entrepreneur that means putting himself in a financial situation where he can pursue his startup with abandon.

If you’ve got leverage in terms of money, status, and time, use it. Exploit those resources to launch the business and life of your dreams.

If you don’t have leverage, work to get yourself in a position where you do.

The second entrepreneur does not cease being an entrepreneur simply by taking a 9 to 5 job. He’ll only cease being an entrepreneur if he quits pursuing his dream in the process.

How about you?

Does the idea of creating leverage, so that you can pursue your dreams and passions resonate with you? Or do you ever use the fact that you could have more leverage to keep you from taking action? Leave a comment.

Please note: I reserve the right to delete comments that are offensive or off-topic.

Leave a Reply

11 thoughts on “Follow Your Heart, Respect Your Situation

  1. Ryan, I’m so impressed with you! I’m loving reading your blog and am so happy for you – you are rocking this coaching thing!

  2. Hi Ryan–your a real inspiration with your blog! The amazing thing is that if dorky guy like you can succeed, anyone can. Thanks for your work and I look forward to reading more. You’re a great guy! Brian (NYC)

  3. PS–economies of scale, Mark Zuckerberg is much dorkier and nerdy than you, so don’t take this in the wrong way.

  4. This is great advice! Nothing is cookie cutter, great point to remember when turning to others for input =)

  5. Ryan,

    Another good post. More good advice. Years ago as I made the leap from career to passionate pursuit I was always analyzing the change in terms of risk / benefit ratio and finding the line between faith and foolishness. Ultimately, I decided that it would be better to fail personally while trying to enrich the lives of others than to succeed at being safe and mediocre. While my bank account is empty and my body aches with the memory of adventures, my heart and life are full of the love of those I have been privileged to pour into. Many times the line between faith and foolishness is only visible in the rear view mirror.

    • Wow, Tom. That sounds like quite an adventure. I love the bookends of faith and foolishness. Like you said, it takes some experimenting to know which is which.