Ask The Hustle: Is Entrepreneurship Right for Me?

Download Now: Free Sales Plan Template
Sara Friedman
Sara Friedman



A while back we invited you to slide into our DMs, and almost 300 of you wrote in with questions. We got some good ones, and we’re getting back to you here. This one’s from Ben in Chicago, Illinois: 

“I’m currently marinating in the thought of becoming an entrepreneur. What should I consider to help me decide if the jump is right for me?” 

Ever had a particularly brutal week at your corporate job and wondered if you should strike out on your own instead? You’re not alone — entrepreneurship can seem like an appealing avenue for many. 

But the reality isn’t always rosy: Starting your own business means taking risks, working tirelessly, and many times walking away with nothing. 

Raleigh Williams, a serial entrepreneur who took the leap from his stable job as a lawyer to start an escape-room business, knows this firsthand. We asked Williams how he knew it was time to make the switch, and what others should consider if they want to do the same:

Ask The Hustle
  • Get a reality check: Entrepreneurship seems glamorous from the outside. But we tend to hear about companies that beat the odds, not the ones that grinded for years just to break even.

    It’s important to get a grasp on what starting a business will actually look like. A major point to keep in mind: If your goal is to work less, entrepreneurship is not the answer.

    “I work a lot more hours as an entrepreneur than I ever did at a law firm,” says Williams. “As an entrepreneur, you never get that relief of leaving at six o’clock and saying ‘not my problem.’”

    Also be prepared to take a pay cut. Founders are rarely able to pay themselves in the early days of their business, and often have to take out loans and make personal investments to get the company off the ground.

    Williams cautions not to follow the widely given advice of “chase your passions.” Instead, zero in on real issues to solve and opportunities that will set you up for success and profit. 

  • Dip your toe in: Luckily, it doesn’t have to be all or nothing — you can test the entrepreneurial waters while you still have your full-time job. Many things are harder once you’re unemployed, including taking out loans to fund your new venture.

    Williams began by networking with other entrepreneurs while he was at the law firm, and quit once he’d found business partners and an idea that would require his full time and attention.

    He suggests reaching out to startups and entrepreneurs you want to emulate, and offering to work for them for free or provide a service, depending on your skill set and the needs of the company. This will teach you what goes on behind the scenes while you maintain a full-time job.

    Skip the contemplation when it comes to becoming an entrepreneur, and channel that energy into experimenting with doing so.

    “Spend $100 toward your idea this weekend,” he says. “It’s probably going to be lit on fire, but it’s better than spending it at Starbucks or the movie theater. Have a propensity toward action.”

  • Follow an opportunity, not a title: Williams cautions that “entrepreneur” is not a job title one should chase. Those interested in starting their own business need to be focusing on a specific problem they want to solve, or an opportunity that presents itself.

    Williams says he never wanted to be in the escape-room business, but he took the opportunity because he believed he could realistically make money doing so.

    Stay realistic, and break off smaller, more doable projects and problems when you’re just starting out.

    “Find something that changes your world, not the world,” he advises. 

  • Bottom line: There’s no easy answer when it comes to taking the jump into entrepreneurship. All you can do is build a network and support system, minimize risk where possible, and use your existing skills to your advantage.

    When a viable opportunity presents itself, it could be the time to take the jump. And the more your network with successful entrepreneurs, the more likely that is to happen.

Subscribe to The Hustle Newsletter

What did you think of this article? 

Give Feedback




Related Articles

Outline your company's sales strategy in one simple, coherent plan.

    Powerful and easy-to-use sales software that drives productivity, enables customer connection, and supports growing sales orgs