Think quitting your day job is hard? Wait for what comes next

Struggling with the decision to quit your day job and start your own small business? Try seeing the choice not as a panacea, a fairy-tale ending, or an escape from your problems, but for what it really is: a big step on the long, twisting, arduous, challenging, beautiful, fulfilling path of small business ownership.

For entrepreneurs and small business owners, perhaps no moment is more fetishized than the one where you finally quit your day job.

Google “quit your day job” and hundreds of articles will pop up:

5 Reasons to Quit Your Day Job

10 Things to Do Before You Quit Your Day Job.

Why You Should Wait Before Quitting Your Day Job

How to Know When You’re Ready to Quit Your Day Job

I wrestled with the question of whether and when to quit my day job for more than two years. The decision became so enormous and significant in my mind, it seemed like the most challenging choice I would ever make. I felt certain that if I could just work up the courage to quit, and turn my filmmaking side hustle into my full-time occupation, then the rest would come easily.

I’d be an artist and business owner, brave and bold in all my decisions, steadfast and sure of my direction now that I was the one steering the ship.


I don’t have advice about whether to quit, or how to know when you’re ready (after two years of agonizing, I eventually flipped a coin), but I do have a few insights from my own experience to put some perspective around what it really means to quit your day job, and what it doesn’t.

Quitting isn’t the hardest decision you’ll have to make
For me, the decisions got much harder almost right away. Within the first month of going full-time with my business, I had to decide whether to spend $10,000 of savings to fix a massive data loss or risk losing our company’s very first clients.

I’ve missed countless nights of sleep wrestling with whether to let an employee go. I’ve had to choose between taking on a client who I know will be a bad fit, or not being able to make payroll. I struggled with whether to make a massive pivot from what my business was known and lauded for (filming weddings) to what I really wanted to be doing (creating documentary content about important issues).

I spent years pondering whether to follow my heart to move across the country, leaving behind the safety net of the place where my business had been established to start over in the more challenging and competitive city of Los Angeles.

The decisions have not become easier. If anything, as my business has grown, each choice gets a little bit bigger, a little bit harder, there’s a little bit more at stake.

Quitting does not lead to “happily ever after”
I equate the way most people feel about quitting their day job to the way most people feel about marriage. There’s this wildly naïve and utterly false sense that you’ll say “I do” to your small business and live happily ever after.

Much like when you get married, you’ll feel a rush of excitement. Your friends and family, even if they expressed some doubts about the choice, will shower you with congratulations and well wishes. You’ll feel hopeful, optimistic, full of plans and promise for the future. 
But like in a marriage, no one sails off into the sunset. Oh no, the commitment is the beginning of years of hard work. You won’t know what you’re doing at first. You’ll make mistakes. There will be misunderstandings, fights, tears. You will daydream about the good times with your old day job, with its reliable paycheck and cushy benefits plan. You will ask yourself, regularly, if you made a huge mistake.

Many people will break up with their small businesses, polish their resumes and return to a life of full-time employment. And the rest of us? Well, we keep working, keep believing and keep marching on. But the day it becomes happily ever after? While there are many joyful moments along the way, small business ownership isn’t a fairy tale.

Quitting does not magically transform your life
I thought that quitting my day job meant that everything I did from that point on would be much different, and much better. I left my job in advertising because I was tired of the stresses and strains of client account management and wanted to do more creative work. And, in fact, I get to do a lot more creative work, it’s just that I get to do it on top of client account management and whole host of other dull but essential administrative tasks which are only marginally less boring to do for your own business than for someone else’s.

Worst of all, and this was the really big letdown, my weaknesses didn’t miraculously go away when I quit my job. I’m still a people pleaser who takes on too much work and gets distracted by other people’s missions. I struggle with a “nothing is ever good enough” perfectionism that makes it hard to release work into the world. I focus too much on worst case scenarios, and sometimes let it cripple my ability to see opportunities.

I did all of these things throughout my career, and I brought them all into my business where, unfettered, they grew to disproportionate levels until I decided to work through them with a bevy of self-help books and twice-monthly coaching sessions. I’m a much better person for doing this work, and over time I have really changed and — dare I say it — improved, but it was a long process and not some miraculous transformation.

So am I telling you not to quit your day job? Not at all. What I’m saying is to see the decision to quit your day job not as a panacea, a fairy-tale ending, or an escape from your problems, but for what it really is: a big step on the long, twisting, arduous, challenging, beautiful, fulfilling path of small business ownership.

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