How do I know if I should quit my job and work for myself?

And if I try it and don’t like it, will it be difficult to go back into the corporate world?

Dec 13, 2023

Ask a Career Coach

I’m a marketing director for a tech company, and I’m ready to leave for my current job for several reasons—I no longer feel excited by our mission, my budget has been cut, and we’ve already had several rounds of layoffs.

I also know I’m a bit burnt out because I’ve been interviewing at other companies, and I keep having the same feeling: The job looks great on paper, but when I start talking about the actual day to day, I feel exhausted.

Many friends have left the corporate world to start their own businesses or consultancies, and I’m beginning to wonder if this might be a path to consider, especially if I can’t find a full-time job I’m excited about. I have some savings (and my health insurance is covered by my partner’s employer), so financially, it doesn’t feel too risky.

But my biggest concerns are: How do I know if I want to work for myself or others? How do I understand if there’s alignment between what I offer and what companies need (i.e., if they have the budget to hire me)? And, perhaps most importantly, if I try it and don’t like it, will it be difficult to go back into the corporate world?

In the midst of a career turning point or crisis? Crux wants to help. Send us your question to be answered (anonymously) by a career coach in an upcoming newsletter.

A Career Coach Says

You’re in good company. As of June 2023, new business applications are on track for the second-largest annual total on record. And you’re asking the right questions.

Here are a few more:

What is your tolerance for risk and uncertainty?
How self-directed are you? Do you need a team to thrive?
How comfortable are you with discomfort?
How comfortable are you asking for help?
Beyond not finding a job you’re excited about, what is your “why” for creating a business?

As with most things in life, there are no guarantees.

In terms of finances, it’s great that your health insurance is covered, as this can be overlooked when leaving the corporate world. It’s also great that you have some savings.

My recommendation is to trim your expenses to a degree that you’re comfortable with and have savings in the amount of six months of living expenses, plus six months of estimated business expenses. This approach removes the pressure to produce revenue from Day 1.

It gives you the runway to test your business development efforts, service offerings, pricing, and target market. And because you’re not operating from a place of scarcity and fear, you can bring a bit of lightness to what you do.

When it comes to alignment between your offer and what your target market needs, start by researching before you leave your job. Gain an understanding of your potential clients—their pain points and desires—and how you can address those with your services.

Then go out with your best set of assumptions based on your research and start having conversations with potential clients. This is the only way to know for sure if there is a match (or not) and get valuable information in the process in terms of your offering and your pricing.

As for returning to the corporate world, I suggest giving yourself a year in your business to see if: 1) you like it; and 2) you can make it work.

If you decide it’s not for you, returning to the corporate world is possible. How difficult it will be depends on two factors. The first is the mindset shift necessary to go back to the role of employee and the second is the current state of the industry you left at the time you hope to return. The first is within your control. The second is not.

And there’s one question from a potential employer you should be prepared to answer … “Do you see yourself leaving to run your own business again?” They’ll want some assurance that an investment in you won’t be lost anytime soon.

Five (not-so-random) tips:

Learn how to pitch, sell, and close business (the resources below are a great place to start).
Think about how you want to do business and what you want the client experience to be.
Have a support network to ask questions and have a sense of community (it can be lonely otherwise).
Focus on your mindset—it matters.
Set boundaries for your work and personal life.

Wishing you much success no matter the choice you make.

– Katherine Danesi

Meet the Coach of the Week: Katherine Danesi

In her own words:

I began my career in sales, marketing, and management. For 12 years, I worked at a Fortune 500 company, followed by a series of startups. I managed teams in sales, customer support, operations, and marketing. I hired, fired, and project managed. I launched new initiatives within large organizations and new organizations outright.
It sounds great on paper, but I was frustrated and lost, climbing the corporate ladder and then claiming my territory in a competitive startup culture. While I was pouring my energy into growing others’ businesses, I longed to pursue my own vision of success, if only I could figure out what that was.
I received a gift when the last startup I was working for lost its funding. I didn’t necessarily feel ready for entrepreneurship (really, who does?), but I found my footing as a Business Coach + Strategist. From creative solopreneurs to non-profits, I've spent the last 10 years helping high achievers launch, grow, and pivot businesses that align with their values so they can live a life of purpose and impact.

Crux Subscribers: Set up a free Discovery Call to explore and get feedback on your business idea (and sign up for Katherine’s weekly email full of business and life advice while you're there).

Katherine’s Go-to Resources

Instagram Reel: 3 Things I Wish I Had Known Sooner (by me)
The New York Times Best Seller: Two Weeks Notice: Find the Courage to Quit Your Job, Make More Money, Work Where You Want, and Change the World by Amy Porterfield
The Mel Robbins Podcast: Start with “Boost Your Success in 2024: My Best Advice on Business, Time Management, and Reinvention,” but there are so many good ones
The Rich Roll Podcast: Long-form conversations digging deep into topics that inspire, empower, and enlighten.
Allison Davis’ Blog and Sales Roundtable: When it comes to sales, Allison knows her stuff

What We’re Thinking About This Week

(Besides finishing our holiday shopping)

More on the “should I work for myself or others?” question.
For anyone on the fence, this new office surveillance trend may help answer your question.
Out of practice for your office holiday party? Here are a few good tips.
Despite the “lazy girl job” trend, women’s ambition is higher than ever.
… but those ambitions also include sleeping 14 hours a night.
… and taking more self care and mental health days in 2024.