Off the curb

Feeding the Meter



Check out our Off the Curb profile stories and you’ll see examples of people who have jumped career lanes or started a business to get off the curb! Justin Lind, jumped from mechanical engineering to become a remote fitness expert and Lynn Von Schneidau left a business position to become a naturopath and creator of unique wellness retreats. Although career success stories and entrepreneurship lore is full of mavericks who “gave-up-everything-living-off-Ramen” to pursue their dreams, quitting your day job cold turkey may not always be the best option! The old adage “it’s better to look for a new job when you already have one” often holds true because you don’t have the added stressor of figuring out how to pay the rent. In fact, according to research done by University of Wisconsin professors Joseph Raffiee and Jie Feng who followed over 5000 entrepreneurs over a 15 year time period, you are 33% more likely to be successful if you keep your current position while simultaneously starting your new venture. Raffiee and Feng call this “hybrid entrepreneurship.” So although it’s tempting to tell your irritating boss to take a hike while you pursue your dream of importing Peruvian coffee, unless you have a cushy nest egg, don’t mind living on your best friend’s futon, or have a significant other willing to pay the rent, if you can hold onto your current spot while you get your business going, statistically the odds will be in your favor!

See our profile story on Michelle Aronson who is a great example of doing this well. Michelle worked full time at a university until she could build a substantial following for her farm-to-table cooking school called Farmbelly. New York Times best selling author Sebastian Junger is another example. Junger grew up down the street from me in a Boston suburb and went off to Wesleyan to study cultural anthropology. He had an interest in writing early on but worked as a tree arborist while trying to improve his craft. He routinely scaled 20 foot trees with a chainsaw glued to his hip before an injury sidelined him and he narrowed in on his writing; eventually hitting it big with his novel-turned film The Perfect Storm. His writing also parlayed into authoring more books (including A Death in BelmontWar and Tribe) and becoming an award-winning war correspondent, ABC news contributor, and documentary filmmaker.

David E. Kelley, writer and producer of hits such as Ally McBeal, The Practice and the HBO mega-hit Big Little Lies also had a dual career for a while. Kelley (also from my hometown) graduated with his J.D. from Boston University and practiced real estate and criminal law for a few years while he worked on a screenplay on the side. He found an agent who sent his screenplay to T.V. producer Steven Bochco who was so impressed with the young lawyer’s work, he hired him as a story editor for his then-new-show called L.A. Law but Kelley kept a dual career going and took a leave of absence from his law firm to move to L.A. to test the waters before quitting his job. Eventually he left law and concentrated on writing and producing full time. Paloma Contreras, an international design influencer with over 100 thousand Instagram followers is also a hybrid entrepreneur. She kept her job as a high school Spanish teacher while working on her passion project, a design blog called La Dolce Vita, before she had enough of a following and interest in her interior design services to leave teaching.

Photo by

Photo by

Neil Blumenthal, Andrew Hunt, David Gilboa, and Jeffrey Raider better known as the founders of the billion dollar eyewear company Warby Parker, also made a strategic choice not to quit their jobs or schoolwork to “go all in” with their entrepreneurial venture when they were just starting out. Despite getting business advice to the contrary, and working nights and weekends took a toll, by building their business in parallel with their current commitments, they were able to test their idea and build confidence in pursuing it. (For a little more insight into the Warby Parker founders decision-making, check out best selling author and Wharton Business school professor, Adam Grant’s Ted TalkThe Surprising Habits of Original Thinkers. Bucking the idea that all career changers and entrepreneurs need to be ambitious, full-time risk-takers, Junger, Kelley, Contreras and the Warby Parker founders combined their risk taking with risk-mitigating by balancing their ambition to fuel creative and business pursuits with a level of financial security and freedom they were comfortable with.

According to the Small Business Association roughly 30% of new businesses fail in their first year, and while that’s not a reason not to pursue your passion, it’s something to consider. Additionally if you make more than $60K a year, experts suggest it will take you 6 months to find a new position. So before you put it all on the line in your hopes of being the next Richard Branson, take a pause and think about the following:

1. Do you have enough in the coffers to sustain you (and your family) for 6-9 months?

According to most financial planning experts, you should have enough saved or enough coming in to cover your expenses for 6-9 months before quitting your job. In my coaching practice I’ve had several clients who quit on the spot only to regret it later, adding a great deal of stress to their personal lives, as they underestimated how long and how many additional resources would be needed to get their side hustles into a profitable position. While excited and anxious to follow their pursuits, both career changers and new entrepreneurs routinely underestimate the cash equation which can bury dreams pretty quickly. “One of the main reasons most small businesses fail is that they simply run out of cash,” says Cynthia McMahon, Founder and CEO of business plan software company Enloop. “Writing a business plan without basing your forecasts on reality often leads to an unfortunate, and often unnecessary, business failure. Without the benefit of experience or actual historical financials, it’s easy to overestimate a new company’s revenue and underestimate costs.”

Photo by Impact Hub

Photo by Impact Hub

2. Have you run your idea by a non-biased group of people to get a feel for the marketplace?

Where would you be without your encouraging friends, family members or mentors who encourage you to follow your heart’s desires. These relationships are invaluable in building a nurturing and supportive community and giving you a safe place to talk about your dreams. But I’ve also seen career changers and would-be-business owners jump into things without additional feedback. Equally valuable is the tough but honest feedback of people who might potentially hire you or use your products or services. If you’re changing careers, do you need to gain additional skills or experience? If you’re starting a business remember its not only about people liking your idea, it’s about people paying for it. So while you might have a website worthy of a design award, your girlfriend thinks you’re the next Bill Gates and 10K people are following you and your travels to Machu Picchu on Insta, if you don’t have a product or service people will pay you for, you don’t yet have a business. If you aren’t sure how to find people who will give you objective feedback, think about joining an incubator or shared working space like an Impact Hub which offers a range of services for its members, from free mentorship to business planning workshops; lending the right dose of equal parts optimism and reality to support budding bootstrappers. Most likely you’ll find someone who can look at your plans with an objective and knowledgeable eye. (Impact Hub offices are located in most US cities and many other cities around the world.)

3. Have you evaluated the “big boulders” in the way of pursuing your dream?

At Off the Curb we’re big on the “vision” thing. If you’re skipping off into the sunset it’s good to know where you’re skipping to. Your clear vision about how you want your career or business and life to be is the foundational piece in keeping you motivated, inspired, and looking ahead. Most career changers and aspiring entrepreneurs have strength in “visioning” but that’s not the only skill or attribute needed. I like C.D. Jackson’s quote, “great ideas need landing gear as well as wings.” It’s great when things take off but you also have to have the right details in place (such as process and infrastructure) to keep things grounded and make them happen. This is the less than glamorous part of changing careers or heading into entrepreneurship and can derail even the most optimistic people. I always encourage potential entrepreneurs to look at the 3 biggest “boulders” in their way. Whether it’s time away from kids, a weakness in digital marketing, fear of raising capital, or a product or service that’s not exactly flushed out yet, it’s important to look at what could potentially slow you down and come up with the best plan of action to proactively plan for, and get out in front of potential problems.

Pursuing a dual career or hybrid entrepreneurship is not easy. Maintaining a positive performance in your current position is important and most professional positions require more than the standard forty hour work week, but mitigating your risk with measured steps rather than a “big dive in” might be a way forward.

A recent LinkedIn” Purpose at Work Report” revealed that 74% of respondents wanted more meaningful work. As my late, dear friend Dana said when she knew she would be leaving us“ it’s a short spin on a little blue ball;” a reminder of how valuable our time here is. Whether our work is full time parenting or pioneering, most of us aspire to do work that’s fulfilling, and makes a difference. Perhaps a dual career or hybrid entrepreneurship is the right way forward for a career and life that’s meaningful for you.

Lynne Cage