6 Tips from Entrepreneurs Who Quit Their Jobs to Pursue Their Dreams


Escaping the cubicle life seems to be all the rage these days. Everyone wants to “live the dream” or follow their passion without the bother of working full-time. In fact, a survey conducted by EY in 2016 reveals that 62% of millennials have considered starting a business.[1] Another survey, LinkedIn’s 2016 Purpose at Work report, revealed that 74% of respondents want meaningful work.

There’s no doubt about it, so many people have entrepreneurial ambitions and many more desire to do something in their career that matters. This boils down to a group of folks who will inevitably quit their job to pursue their dreams.

Of course, working for yourself can be incredibly fulfilling. However, if you make the move prematurely or without much planning, you could jeopardize your dream’s success.


Whether you want to travel full-time, give back for a living, or start a business, you should hear from others who’ve made the leap. Hopefully, these collective stories and advice will not only inspire you, but also help you prepare to pursue your dream with confidence.

Have a Vision

Before you go skipping off into the beautiful sunset, you want to be very clear on where you’re skipping off to. You might have passions and interests in many areas, but you’ll need to nail down exactly what you expect from your dreams.

For example, you might be passionate about owning a business, but a life that involves entrepreneurship can take shape in so many ways. You could start your own business, become a consultant to other small business owners, or even work with kids in youth-focused tech incubators.

There are many directions your dreams can take you. The other complication is that these directions can change. You could start a successful business, sell it, and still have the rest of your life to pursue other dreams.


The point is that you should create a vision of what your dream-filled life will look like. How will you build your empire? What are the ways you can capitalize on your dream and start your business?

Eraina Ferguson, founder of My Good Life Now, an online resource for parents of special needs kids, has seen her business model morph in many ways many times. At the end of the day, it’s always been about helping and connecting for her.

She says, “It’s okay to change direction, but if you have a vision in place, you’ll always end up at the same place—even though the path you thought you’d take to get there becomes different.”

Research Your Field

Don’t let your dream career turn into a nightmare due to lack of research. You might have a vision of what life would look like as a seaside surf-shop owner, but the reality of running that business can be starkly different than what you envision.

Though you shouldn’t chuck your dreams and go back to the drawing board right away, you should research what it takes to pursue your dream business or lifestyle. If profitability is elusive, find out why and see if you have the resources to deal with that risk.

Jhonn Thomassen is the owner of Marine Park Coffee in Brooklyn. He quit his job as an advertising account manager to pursue his dream of starting a coffee shop. Thomassen suggests that research and resourcefulness is a must. He says, “Interview as many people as possible in the field you are going into and to take full advantage of any small business services your town or city provides.”

Create a Financial Plan

Having a financial plan is crucial to supporting your dream. Otherwise, you could be hindered by lack of resources and financial pressure.

Shai Littlejohn worked as a lawyer for 15 years before becoming a musician and a songwriter. Five years ago, she decided to pursue a career in music. First, she started a part-time law practice, then auditioned for Berklee College of Music in Boston, and then moved to Nashville. Littlejohn says the move has made her much happier with her life.

In terms of tips, she advises would-be dream chasers to “put a 12-24 month financial plan in place and execute it before you leap.” She explains, “Your dream will require finances, so make a budget and include that in your 12-24 month plan.”

Don’t Quit Your Day Job (Well, Not at First)

Of course, your goal is to quit your job so that you can pursue your dream, but understand that timing is crucial. If you’ve been diligent enough to craft and refine your 12-24 month plan, you should now be on the road to quitting your job. However, make sure you have some, if not all, your ducks in a row before making the leap.

Meredith Jaeger was a customer service representative at a tech company in San Francisco when she sold her first novel, The Dressmaker’s Dowry, to publisher HarperCollins in 2015. Just a year later, she was able to quit her job and now continues to write full-time.


Jaeger warns, “Keep your day job while working tirelessly towards your dream job.” She was working hard outside of her job to make her writing dream a reality: “I wrote on weekends for years while working 9-5. I wrote four novels before I finally sold one.”

It might be tempting to just make your move quickly, but it’s okay to build while you have a safety net in the form of a job. In fact, it’s probably the best way to give your dream the best chances for survival and success.

Have an Emergency Fund

There’s nothing more stressful than launching out on your long-awaited dream only to have little to no resources to support it. Famous poet Langston Hughes wrote about deferred dreams—they can become a burden to the person who can’t bring them to fruition.

One way to avoid restricted cash flow while building your dream is to have an emergency fund.[2] Ideally, you’d have one for both your personal and business expenses. Scott Churchson is a financial planner turned actor and stunt performer. He’s been in both popular TV shows along with commercials and works, full-time, in the entertainment industry.

He admits that much of his success is because of his background in financial planning. He describes his “emergency fund that had been built up over the years” as particularly helpful during slower periods in his acting career.

Don’t Burn Bridges

Leaving your job can be one of the most freeing, exhilarating things you can do for yourself. If you’ve planned well, hopefully, you won’t jump ship right away. It can be tempting to get “senioritis” because you know you’re leaving. Fight the urge to do less than stellar work or slight your co-workers in any way.

When it’s time to go, do it with class. Jessica Tappana is a licensed clinical social worker who recently started her own, independent practice. She says that it was important to leave her employer on the best terms possible. “I did everything I could to help my former job prepare for my replacement,” she says.

She’s aware that she’s still connected  to that community even as a small business owner: “I know that the mental health community is small and my former employers may be able to refer potential clients to me.”

Breaking the mold and going for your dreams isn’t the easiest thing in the world. There’s a ton of risk involved, and it can be incredibly scary to make the leap. Once you quit your job to pursue your dream, you’ll likely find that it was all very worth it—the planning, researching, saving, etc.

Hopefully, these tips will help you make calculated risks that will pay off in the long run. Happy dream-chasing!

Article Sources:

  1. NPR.org. “Millennials Want To Be Entrepreneurs, But a Tough Economy Stands in Their Way
  2. MeetFabric.com. “Emergency Fund: What Families Need to Know

Aja McClanahan

Aja McClanahan is a financial writer who blogs regularly at www.principlesofincrease.com and also writes for other online publications covering personal finance, entrepreneurship, travel and general lifestyle topics.

Read Full Author Bio