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Making the Break: Steps to Consider Before Quitting Your Day Job

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  • Post last modified:September 27, 2021
  • Post category:Business
  • Reading time:7 mins read

If you find yourself dreaming about what it would be like to start your own business. How would it feel to take the leap? What do you do to prepare? Is the risk simply too great for you and your family? These are some of the questions Jason, a former colleague and friend, recently helped me deconstruct. He has for years now been doing a familiar dance with his desire to launch a startup business but like many would-be entrepreneurs, he defaults to safety whenever he seriously considers breaking with a stable paycheck and secure future.

What will it take to persuade Jason that he’s ready to take the risk? His decision encompasses many elements, and in this conversation, we attempted to untangle some of them.


It’s been six years since Jason first got excited about his startup idea. Since then, he’s wrestled with the decision to go against his parents’ lifelong emphasis on job security in order to take the leap of faith required to chase his dream. He made at least one false start some years back, registering and preparing to tender his resignation at work but he pulled up short before quitting his coveted government job. Instead, Jason felt paralyzed and bargained with time – a strategy he doesn’t recommend. “When you do that, time just goes by.”

Less than 1% of federal employees opt to leave their jobs, and for very real reasons: benefits, pension, post-retirement health coverage. When Jason looks at the costs – both practical and psychological – the path to starting his own business is anything but clear. Despite the pull to stick with his employment status quo, however, Jason continues to nurture his startup vision and feel a strong pull towards pursuing the path not yet taken.


Were financial concerns off the table, Jason knows without a doubt in which direction he’d head. While travel and other niceties would be attractive, doing something meaningful with his life is his goal above all else. He’s seen in the progression of his life huge changes in his personality, overall thought processes and priorities. Today, he’s be looking for an altruistic calling, perhaps involving animals or people.

There’s something hard-wired in all of us that creates an impulse to leave the world a better place and without hesitation, Jason would dive into an entrepreneurial venture and never look back. But so long as he needs a paycheck, the fear is real – and holding him back.


Jason’s father is 86 and still very much believes that you don’t forsake the predictable paycheck. If he knew they were financially secure living solely on his wife’s income as a teacher (and tutoring side hustle), Jason would feel more inclined to take the gamble. Without that, Jason has a hard time flouting his father’s advice.

He wants more than anything to be a good husband and provider. But he might want to consider at this juncture that he could be doing his wife a disservice. It can be empowering as a spouse to take up the slack and support a venture that ultimately will make life more worthwhile. It’s possible to save money by living “below your means,” something many wives are very willing to do in the service of a bigger vision. Jason is fortunate to have that kind of emotional support and vote of confidence at home.


–  Registered his business with the state of Virginia.
–  Familiarized himself and taken advantage of the many online and local Small Business
–  Administration resources and courses.
–  Written both marketing and business plans.
–  Researched the competition.
–  Planned a website.
–  Conceived/designed a roll-out strategy.


At 50, caution keeps pulling Jason back from taking the plunge. But as long as he’s working 40+-hour weeks, he’ll never have that most valuable commodity: the time required. This leaves him stuck, debating with himself about the long odds against successfully starting a new business versus his deep desire to go for it anyway.

With all the preparatory steps under his belt, Jason feels ever closer to reaching the day when he gives himself the permission to jump. Does he feel prepared? Yes. He’s studied, researched and brainstormed the roadmap for his venture, while also honing his skills through his day job. If only he were 30 instead of 50! His anxiety would be in check, the decision would be foregone and he’d be on his way. That day may not be far off.

BOTTOM LINE – Three Takeaways

There are key components to the three-legged stool on which I think the startups that thrive absolutely depend and I shared them with Jason:

1. COMPETENCE: Don’t make the leap until you’ve grown and prepared yourself. Understand bookkeeping, customer base, what the market will support. Get the basics in place and develop the know-how to advocate for yourself.

2.  FINANCIAL: If you don’t have the money to bootstrap it, do you have enough saved to give you some runway? Ideally, save the money and gamble on yourself rather than with other people’s money.

3.  MENTAL SUPPORT: You won’t succeed as an entrepreneur if you don’t have stability and mental wellness. You can’t live in fear, anxiety and sleeplessness, you need people around you that will support, love and encourage you and your decision to take this journey.


–  How Jason started – and then stopped – his dream of starting his own business.
–  Initials steps and what pulled Jason’s planning up short.
–  Articulating the dream: Is this what you would do were you to win the lottery?
–  What building blocks does Jason have in place and what does he still need before being definitively ready to take the leap?
–  The three-legged stool that support successful entrepreneurial ventures. 


“(My upbringing) was always about security. It wasn’t about jumping off the cliff and making that leap to try starting a business. It would be a complete liberation.”

“The thinking phase is done. That’s in the past. I’m active now, just not actively doing it for income, but actively planning it.” 

“When you’re 50, you’re looking at life through an entirely different prism. The decision process is a lot slower and it’s taking a lot of time to make that jump.”

“If you want to make the leap, first and foremost you have to have the skills and competence. If you haven’t got those things, don’t make the leap today. Make the leap tomorrow.” (Mike)

“If you can save some money, invest in yourself, gamble on yourself. It sure gives you a little more motivation and drives you a little harder when you know it’s your piggybank.”

“You will not succeed as an entrepreneur if you don’t have stability and mental wellness just oozing from your brain.”

Resources Referenced:

Small Business Administration:


Mike’s Bio:

Mike Thakur is CEO of WorkLodge and Founder at the Gabriel Project. He is on a mission to change lives through entrepreneurship and sustainable social enterprise. With experience both as an executive roles both at established companies and multiple startups (commercial and non-profit), Mike is committed to giving back and creating environments that leave people better off than when they started.

Follow Mike: (Office & Studio Website) (Personal Website)