Put Your Wildest Dreams on Hold and Keep Your Job
Why you shouldn’t burn your ships until you’re ready
“I could never take such a risk.”
Whenever I explain that I’m self-employed to someone for the first time, they usually have this reaction. It’s hard to fathom ditching a stable paycheck and organizational structure for a world of uncertainty.
But switching from corporate to freelance writing wasn’t a risk — it was a calculated risk. I started freelancing in October 2017. I became a full-time writer in July 2019.
Far from a rash, spur-of-the-moment decision.
If you’re here, there’s a good chance you’re enticed by the idea of quitting your job or doing something radically different. That’s awesome, and I commend you for dreaming bigger.
But don’t quit your job. At least, not yet.
Keep Your Ships Afloat
You’ll see some entrepreneurs advocate for burning your ships — taking an untethered leap into entrepreneurship with no option of turning back.
Inspirational speaker Tony Robbins has even been quoted saying, “If you want to take the f**cking island, burn your f**cking boats…”
The “burn your ships” expression is a modern representation of Hernando Cortes’s order to sink his ships during his conquest of the Aztecs, thus preventing retreat. Essentially, it’s used as inspiration to overcome psychological hurdles, insecurities, and second thoughts.
Although I’m no Tony Robbins, there are two problems with this all-in strategy.
First, it’s historically inaccurate and misleading. Cortes destroyed his ships to prevent dissidents within his expedition from retreating to Cuba. So, yes, he wanted to eliminate retreat — but it wasn’t intended to be a grand gesture or inspirational metaphor to help his forces conquer the Aztecs.
Second, Cortes didn’t burn his ships — he scuttled them, meaning he deliberately flooded their hulls to ground them. I know it’s a trivial correction, and I know “Scuttle your ships” doesn’t have the same ring to it, but still.
Regardless, don’t destroy your ships. It’s one thing to quit your job, it’s another to quit with a detailed plan. That’s what separates a risk from a calculated risk. Rephrasing our inspirational metaphor, don’t burn your ships without plenty of resources and a battle strategy.
To use another cliche, slow and steady wins the race, and that’s certainly the case regarding massive career changes. You’ll increase your chances of success if you ease the transition to entrepreneurship by growing your business from a side hustle first.
Start With a Side Hustle
In an ideal world — one where money didn’t matter — you could pursue your wildest dreams without considering the financial consequences.
Unfortunately, we don’t live in that world. Money matters.
While it’s not as immediately liberating, starting a side hustle and growing it into a legitimate business is much more feasible because you don’t sacrifice the stability of a biweekly paycheck. If your business doesn’t take off as quickly as expected — or you realize there are a lot more steps between you and profitability, you’ll still have a job that can support you.
That said, there is an obvious trade-off: you have to sacrifice free time to prioritize your business. And if you don’t have free time, you have to find time somewhere. That means working instead of watching TV or leisurely reading a book. Or even waking up earlier to carve out time for your business before your day job.
For two years, I doubled as a corporate banking analyst and a freelance writer. The vast majority of my time went to my day job, but I dedicated the rest of my time and energy to writing when I could spare it. Was it hard? Yes. Was it frustrating to grow so slowly? Absolutely.
But it eased the transition. It allowed me to test the waters without taking a significant, irreversible risk.
Looking back, I probably could’ve stayed in corporate banking even longer. But I reached a point where I didn’t need to anymore. I wasn’t just itching to quit — I was prepared to quit.
How to Know When You’re Ready to Quit Your Job
It starts with answering a question: Why are you leaving your job?
“The hours are grueling.”
“I’m not paid enough.”
“My work isn’t valued.”
“I don’t feel like I’m making a difference.”
These are valid reasons for job dissatisfaction — but they don’t support quitting.
“I landed another job.”
“I saved up enough money to cover my expenses for a year.”
“I already secured a client and recurring work.”
“I assembled a team and investors.”
These statements indicate you’re prepared to quit. When you’re prepared, you can point at logical reasons for why you’re leaving your job.
After two years of preparation, I could quantitate my readiness to quit my job. I created a checklist of conditions that I had to meet before I’d allow myself to exit the corporate world. Here was my list:
- A year of runway for financial stability and peace of mind
- A portfolio of ten posts, including samples on my website and guest posts on others
- A website to house my portfolio and promote my services
- A semi-decent writing process (i.e. idea generation, outlining, etc.)
- A steady client
Trust me, when you can quantitate your readiness, going through the quitting process is much easier. It’s still a nerve-wracking experience — my heart raced like a pinball stuck in an infinite loop between two bumpers. But if you complete your list of conditions, it’ll serve as logical ammunition to support your decision.
Then you can finally sink your ships.