By Joel Ombry for GROW

Working for oneself is an idea sown deep into the fabric of American life. The United States is one of the most entrepreneurial cultures in the world. However, for most it’s far easier to talk about taking the leap from working for others to working for yourself than actually doing it. In a 2018 study sponsored by Vistaprint, while 62% of Americans wanted to own their own business, only 14% considered it a realistic goal in that year. 

It’s a scary proposition to leave the security of a steady paycheck and a narrow set of decisions to dive into a world where not only is the income uncertain and totally dependent on you, but you are the decider-in-chief for literally everything. 

This issue is very personal to me, as I’m in the process of retiring from a company where I’ve spent more than 25 years to pursue writing, consulting, and non-profit work. While I usually interview others for these articles, this time around I’m “interviewing” myself. The first question that came to mind is how do you deal with the uncertainty and fear? 

The first step: Know your why 

There are few things in life as compelling as a person on a mission. Knowing the reason you are doing something, with crystal clarity, provides motivation and determination when times get tough. According to Guidant Financial, the top three reasons people decide to launch their own businesses are as follows:

• 26% wanted to be their own boss

• 23% wanted to pursue a passion

• 12% wanted to get away from the corporate environment

I’ve spent a long career in the corporate world with a great employer and have no regrets. The people I met and the opportunities it afforded me create a rich tapestry of memories that I’m grateful for. However, age and changing circumstances sometimes reorder our priorities. 

This can happen gradually as kids grow up and begin to make their way in the world, or suddenly such as when a major illness strikes and you realize that the road ahead is not endless. I’ve experienced both in the past two years as my youngest son finished college and I survived cancer surgery in 2018. My “why” to strike out on my own was shaped by these circumstances. 

The second step: Do your due diligence 

Once you know your why, it’s time to get to work. Thorough preparation will not only guide your effort but help you move forward with confidence. Some important steps in this journey are as follows:

• Make sure your business plan and financial picture are thought through. What will your monthly expenses be? How much of your former income do you expect to earn, from what client base? Over what timeframe? Get professional help if you need it and estimate conservatively. Ideally, you’ve been pursuing your side hustle for some time and you’ve got a sense of the work required to ramp up to full time if that is your goal.

• Ensure you plan for health coverage and other protections formerly provided by your employer. Healthcare options include moving onto a spouse’s plan or shopping on the healthcare exchanges. Include these in your financial plan.

• Develop a support system. While entrepreneurs wear many hats, they can’t be an expert in everything. Identifying advisors on certain topics will help you navigate challenges requiring more specialized expertise (such as legal, financial or technical) These advisors can include organizations such as GROW that have resources specifically targeted to small businesses.

In addition to the major financial and workday changes you’ll encounter, there is an emotional side to a change of this magnitude that you shouldn’t underestimate. To some, a job is part of their identity and their co-workers are an important social tribe. I’ve worked in large organizations my entire career. The potential for feeling isolated and unsupported is very real. Just as you should develop a support network of experts as part of your due diligence, an emotional support network is just as important. 

Remember you’re not alone

West Michigan is known for its entrepreneurial ecosystem and there are hundreds, if not thousands of startup business owners who’ve all taken the leap. Connect with others, ask them questions and learn from them. Take advantage of all the different organizations and groups who host events for entrepreneurs and those currently working their side hustles. When you’re ready, you’ll know it.

Joel Ombry lives in Grand Rapids Michigan and in addition to a corporate career writes about business, fitness, and politics.