Should I quit my day job and go all-in on my passion, or work it on the side?
I’ve interviewed hundreds of people who have made major midlife career shifts from larger organizations into the wacky world of entrepreneurship. My personal approach has been much more leap, scramble and work like crazy to succeed (or not, lol) before my money runs out. But there’s also a strong lifecycle connection to the approach you might consider.
The further you get into life, the harder it is to execute the “leap and pray.” Click here to tweet this
You have more responsibilities, more to lose, and the perceived pain of failure becomes a bigger emotional and psychological barrier. Not to say that it cannot or should not be done, just that the trappings of inertia become harder to release with age.
The way most adults with responsibilities (and without big cushions/investors) do it is to:
- Keep the main gig strong and
- Work the passion job on the side
Question is how long do you do this? Answer – until one of three things happens:
- Until it’s swappable – The passion project reaches a point where it’s generating enough cash to essentially make an even swap with the day job.
- Until it’s projectable – The growth and revenue trajectory is becoming clear and consistent enough to make you believe that the passion project will go where it needs to go within a short enough window to be covered by a cash reserve. Then, you take a leap of faith once it’s most of the way there and work like crazy to make it happen.
- Until it’s untenable – You learn that your initial assumptions were wrong enough to make the project untenable. At that point you either need to walk away or explore whether this new information is giving you a new roadmap for success a different way. And even then, you need to ask whether that different way will still still excite and inspire you. It may make the venture financially viable, but will it still be soul viable?
When I was working on Career Renegade, I interviewed an orthopedic surgeon who took 20 years to build into his next career as the founder of Kona Joe coffee in Kona, Hawaii (that’s Joe in the photo above). It would have taken longer, but he had to go all-in to raise the money needed to take the passion project to the next level. He was still travelling back and forth from his home in Orange County, CA where he still practiced medicine, to Kona.
To keep growing Kona Joe, Joe and his wife, who is his partner in the business, needed to buy some big equipment that would have to be financed by selling their house in California. That would essentially mean the end of Joe’s practice. It was a tough decision, what I describe in Uncertainty as a creation “crux move.” The choice you make in that one moment defines a cascade of major outcomes moving forward. This was a make or break moment for Kona Joe. They sold. And never looked back.
One other really important point here – keep your lifestyle in check along the way.
Once the passion project starts making a bit of money, if at all possible, do not raise your living expenses to consume that extra income. Bank the money instead. Because if you ratchet up your lifestyle to consume all of the income generated by both your main gig and your passion project, when it comes time to make the leap, you’ll end up earning only half what you now need to live. Bad math. Bad move. And the anticipated pain may well be big enough to keep you from ever making the jump.
So, what do you think? And for those of you who are building something on the side right now, what’s your leap plan?
Share your answers in the comments…
P.S. – If you’d like me to answer YOUR question in an upcoming “Ask JF” column, go ahead and ask your question in the comments below and you could show up in a future post.
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