6 Questions to Ask Before You Quit Your Job to Start a Company
We’ve all had that moment when you wonder about life on the other side. Starting a business. Freelancing. Entrepreneurship.
It’s a funny thing quitting a job you love to do something you know you’ll love even more. In many ways, it’s a very luxurious position to be in. Yet, you still have to wrestle some big questions to the ground. These questions fell into two camps. First, should I do it? Then, if I do, how will it work?
Let’s start with the first set of questions: Should I do this?
1. What’s the Worst That Could Happen?
This little question can and should be asked the moment any indecision strikes. Should I move cities? Should I go for that job? Should I order another martini?
We often put false expectations, pressure and weight on our decisions and assign impact to their outcomes in ways that stretch far beyond their actual capacity. I had to remind myself, repeatedly, that the worst-case scenario wasn’t that bad at all. If my startup failed, and if I couldn’t get enough clients to pay the bills, I’d just get another job.
2. What Happens if I Stay Put?
This was my favorite question, because the answer was clear and immediate. I simply couldn’t. Often, we analyze the cost of opportunity (a jagged line with high highs and low lows) against a flat, steady baseline that represents staying put. But that’s not a fair assessment. If you stay still, especially when you have a burning desire to do something different, that baseline will actually become a downward trajectory. Often, it helps to think of the cost of inaction as a descending force, not a leveler. This reframe can help a clear answer to emerge.
3. What Will I Miss?
I’m not that big into lists, but I wrote a big one of all the things I thought I was going to miss. Most of what was on that list was about the people and friendships I’d made through work. None of which, I realized, I’d really be giving up. The other things on that list were relatively inconsequential (like a well-stocked and curated drinks selection) or things that I could choose to replicate going out on my own (like weekly trend-hunter meetings).
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