How Do You Know When It's Time to Quit Your Job and Start Your Own Business?

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In late 2021, I started my own coaching and consulting business. To some, it was a strange move. I’d been in corporate America for over 20 years and loved being a chief operating officer. My relationship with my boss was perfect, and the company’s values aligned with my own. Nonetheless, I couldn’t shake the urge to strike out on my own and try my hand at becoming a bestselling author and motivational speaker.

For years, I’d toyed with the idea of starting my own venture, but something stopped me. I was raised to be risk-averse and an achiever, so I’d spent my 20s feeling grateful for job security and a need to climb the corporate ladder — yet something was missing. Now I’ve started my own business, and I am so happy I did.

If you’re stuck in the same dilemma I was, here are a few questions you can ask yourself to ensure you’re making the right decision.

1. If you died next year, would you be satisfied?

It’s easy to trick ourselves into thinking we have limitless time. Most people don’t like to admit that we’re aging. Even fewer of us like to openly accept that any of our lives could unexpectedly end. But, these are the facts. In 2015, when my uncle died at age 60 of ALS, something that made acceptance easier (for both him and us) was knowing he had truly lived his life to the fullest. He had left jobs to start his own risky ventures, traveled extensively, built his own home and pursued numerous hobbies. He had no regrets.

In his final months, he challenged me to ensure I was living in accordance with my values and dreams. Later, I realized that if my life ended abruptly, I would always wonder if I could’ve made it as a coach and consultant. I realized I owed it to myself to try because I wouldn’t be satisfied with not doing so.

Don’t assume that tomorrow is promised. Don’t put off your dreams just because you plan to do them “later.” Assume there’s not a surplus of time and then consult with “future you.” If you feel that “future you” would be disappointed in your present-day choices, then it’s probably time to make different ones.

2. Have you uncovered your real purpose?

We all have reasons for what we do, and we all like to believe that those reasons are deliberate and intentional. But often, our brains work on auto-pilot, and it’s our subconscious minds running the show.

It’s likely that you have good reasons for staying in your current gig, but you also have reasons you’re considering leaving it. Make sure you’re crystal clear on what those truly are. Spend some time completely alone and get real with yourself. You might be telling yourself stories about your real motivations. It’s possible that you’re saying you need to stay committed to your stable job because you must support your family. But what if it’s really fear of change and the unknown that’s holding you back?

Perhaps, it’s not that you feel a responsibility to support your family financially, but it’s fear of what your family will think if you fail or struggle. Maybe you’re afraid to disappoint others. Sometimes, when we make time to consciously think about what’s really driving us — free of society’s expectations or questions — we come up with new insight. When making decisions like these, it’s essential you’re 100% clear on your motivations and what’s really driving you.

3. Have you talked with the right people about it?

When we’re conflicted over career choices like these, it’s not uncommon for us to loop others in. Inevitably, others have opinions on what we should do and aren’t afraid to share those. It’s sweet, but be careful whose advice you buy into. Ask yourself if you’ve talked to someone who’s made this kind of choice before or someone you look up to or view as a role model. What about someone who’s objective; someone who doesn’t have a vested interest in this decision? Or someone you expect to give you different points of view?

If all you’ve done is consult with subjective people who tend to view life choices exactly as you do, you’re doing yourself a major disservice. It’s hard to make the best life decisions if all you do is surround yourself with similarly-minded people. Get out of your echo chamber. Be willing to get some differing opinions. It’s also helpful to ask someone who doesn’t have a horse in the race or a dog in the fight for their opinion. If everyone you ask is directly affected by your decision, you might not be getting any input that’s unbiased, and you’re likely to miss something.

4. Is your heart happy?

We tend to think with our heads and feel with our hearts. Sometimes, there’s a tendency to decide personal matters with our heart leading, and professional matters with our head leading. I’d argue that you should consult with your heart on both. Giant career decisions should not be solely based on reason.

You might be able to produce Excel spreadsheets and PowerPoint presentations about why it makes sense to stay because of the sunk costs of your degree, how long it took to build your extensive network, how close you are to a promotion, how the money is good and you have five more years to max out a pension plan.

But, at the end of the day, if you’re not truly happy with your life, that should sound off alarm bells. We get one shot at this life. If you’re devoting 40-50 hours a week to professional pursuits that don’t ultimately bring you great joy, that should be a major consideration. Our jobs should make us happy. If it doesn’t, it’s more than likely it’s the wrong job.

Making the major decision to strike out on your own can be challenging; this much I know. It’s not for everyone, but before you decide it’s not for you, consider these four things.

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