Don’t quit your day job. The cliché advice offered to anyone doing something bold and ambitious, such as starting a new business. It's a common frustration when people offer this unsolicited advice because you feel your ability's being doubted. As it turns out, they're half right, and that you should do both: keeping your job helps you start your business, and grow it steadily and successfully.
The Time I Went All In
It was Sep 2014. After a successful stint as a digital marketing manager for an enterprise that was the #2 retailer on the web at the time, and with several years of brainstorming and business planning, I felt ready to start a new business. I had saved and betted $25,000 on my idea to build a platform that aimed to make basketball training affordable and accessible to everyone around the world.
Taking such a risk as a one-person operation, I couldn’t help but think “go all in or go home.” Common sense suggests that in order to achieve high-risk accomplishments, you need to put in major work, hours, and creative energy. To do one thing, and to do it well. I succumbed to that mindset, and decided that I couldn’t juggle both a 40-hour week day-job and a 20-hour week side business productively.
After all, they say that the American Entrepreneur has to drop everything, work day and night, and live on a shoestring budget just to survive in the early years. It makes so much sense to invest 100% of your focus on one thing to maximize chances of success.
I took that leap, and it turned out to be one of the most ill-advised decisions of my life.
What I Wish I Knew
Although I never regret the decision to go all in, I do wish I had read Adam Grant’s book, Originals: How Non-Conformists Move the World, in which he offers practical evidence why successful people keep their day jobs until their side hustle takes off.
In the book, Grant offers an anecdote about Warby Parker, a company founded by four entrepreneurs who made a strategic choice not to quit school or their jobs, and not to go all in on growing the company. And yet in 2015, Warby Parker topped $100MM in revenue, was valued at $1 billion, and was named the most innovative company by Fast Company, an honor that in the three years prior went to Google, Nike, and Apple. The Warby Parker founders went against our cultural norms that put entrepreneurs on a pedestal as bold, ambitious risk-takers who drop everything to pursue their passions.
They’ve proven you can start and build a successful business without risking it all, and by keeping their day jobs. Why?
Warby Parker and many other entrepreneurs who build successful companies aren’t just risk-takers, they’re risk-mitigators. That is, they offset the financial risks of starting a business with the financial security of working a full-time job. The steadiness of the day job, in turn, allows them to make extremely bold decisions in the business.
“No person could possibly be original in one area unless he were possessed of the emotional and social stability that comes from fixed attitudes in all areas other than the one in which he is being original.”
-Edwin Land, Founder of Polaroid
Working a stable job and running a volatile startup produces a yin and yang harmony in our minds, a balance struck by the most successful people in almost every domain.
Having a sense of security in one realm gives us the freedom to be original in another. By covering our bases financially, we escape the pressure to publish half-baked books, sell shoddy art, or launch untested businesses.
3 Successful People Who Kept Their Day Jobs
1. Bill Gates only left Harvard a year after he began successfully selling software, and even then, he didn’t fully drop out, he applied for a leave of absence to mitigate risk.
2. Ava DuVernay directed her first three films while keeping her day job as a publicist, only pursuing filmmaking full time after working at it for four years and winning multiple awards.
3. Even after T.S. Eliot published The Waste Land in 1922, he kept his day job for another three years as a bank clerk to reduce risk. He then spent the next 40 years working for a publishing house for stability while writing poetry on the side.
The Upside of Working in Corporate America
For all the complaints about working for corporate America, think about this: your desk job makes you think and use your brain differently than if you didn’t have one. If you're the type of person who wants to do something creative, but you find yourself doing 40 hours of mundane, repetitive tasks, you're actually in a better predicament than you think. The stability of that static work could lead to creative outbursts in your side hustle.
Other corporate jobs offer complementary skills, such as people skills, sales, and marketing ability, and they can be transferred and applied to drive growth in your side hustle.
Synergize your Day Job with your Side Hustle
In retrospect, that’s what doomed my startup. I put in all my creative energy, hours, and hustle in just the one thing, and I got tunnel vision. Not having a job that offered me stability prevented me from taking actual risks in the day to day of the business, which prevented me from earning stable revenue or hitting major non-financial business goals.
Within nine months, I decided to go back to work full-time for Oriental Trading and now at TakeLessons, where I continue to learn invaluable lessons, sharpen my skills, and gain greater wisdom about what it takes to start and grow a business.
As far as the building that basketball platform, failure's okay, because if it's something you truly want to do, you don't just get one shot, you have the opportunity to retool, reassess, and try again.
