6 Questions to Ask Before You Quit Your Job to Start a Company

By Annabel Acton, October 01, 2014

We’ve all had that moment when you wonder about life on the other side.

Starting a business. Freelancing. Entrepreneurship.

I’d been wondering for a good year, and I only very recently took the plunge.

Just to be clear, I wasn’t miserable in my day job. Far from it. I just felt compelled to try other things—namely, to freelance and carve out enough time to really get one of my startups, Never Liked it Anyway, off the ground.

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. My 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).

A list like this will tune you up to what you need from your working environment and give you some clues as to what to prioritize when you are flying solo.

On that note, with the decision to leave made, I then asked: How will it work?

4. What Do I Want Each Day to Look Like?

Sure, freedom sounds good, but what does that mean exactly? It’s too easy to classify self-employment as sleeping in, working from cafes, and cherry-picking awesome gigs, but the real question to consider is: What really gets me fired up? I boiled it down to three things: dynamic people, meaty challenges, and making a mark. Knowing this, I’ve committed to only taking on project work if I find it interesting, with interesting people, and when I know I can make a difference. This is now the filter for any freelance work that comes my way.

5. How Would I Introduce Myself?

My work as an innovation consultant, and my title of inventor (yes, really) put me in the camp of people that you actually want to be seated next to at a dinner party. By default, people assumed I would be interesting and bring provocative perspectives to the conversation. It was an easy crutch. I didn’t actually have to be interesting; I just got a very fortuitous ricochet effect that my work brought.

Resigning meant giving up the title, the story, and all the exciting things people generously associate with you. I had to figure out what my new story would be. It had to be something that I felt good about saying out loud—mainly to myself, but also to others when asked. It turns out that being an entrepreneur that takes on projects that make me buzz is a perfect next chapter; and one I’m thrilled to write.

6. How Will I Keep Growing?

Going boss-less is a strange thing. Suddenly you’re in charge of it all. You’re your own lifeboss. This has some obvious perks, but what about the good side of bosses? The side that pushes you to dream bigger? To hold yourself accountable to exceptional standards? And to teach you new skills and perspectives?

Luckily, there’s one easy solve: mentors. I often feel like the luckiest person in the world when I think about the mentors I have around me. Each teaches me something different, each I respect more than anything, and each betters and emboldens my thinking. So, If you’re off to pursue your own thing, get some mentors.

With more and more of the population expected to freelance or start their own business in the coming years, we’re likely to have these sorts of conversations about taking the plunge more regularly. Asking the right questions can help turn your ponderings into a strong gut conviction that it’s the right choice, at the right time. And when that happens, it feels like an inevitability, not a choice.