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Craving to Be Your Own Boss? Do This First

Nearly 10 years ago, I quit my job and started a business. That business ultimately became the coaching and consulting practice I run today. It’s evolved over time. It’s moved from one side of the country to the other, and even overseas. Working for myself is something I always knew I would do, and I’ve never looked back.

Not surprisingly, as a coach I attract many clients who are—or who dream of being— their own boss, too. Many are excited by the work style or the freedom. Some have a brilliant idea to bring to the marketplace. Others hope to marry their personal values to a paycheck by creating work they love, that fits their lifestyle.

The road from employee to entrepreneur, and the motivations for traveling it, are different for everyone. We often hear the two extremes: the laptop entrepreneurs making six-figures working part-time and the statistics on how many small businesses fail within their first few years. The reality is somewhere in between the two.

If you’re itching to ditch the cubicle and follow your entrepreneurial dream, here are a few things to do before you write that resignation letter.

Define what success looks like

If one year from now, you were living your entrepreneurial, self-employment dream, what would it look like? Take the time to explore what types of work you’d be doing in that dream scenario, who you’d be working with and how many hours you’d be putting in for what level of income. What’s your work-life balance equation? Consider the life you want to be living one year from now and five years from now and be honest. This isn’t about someone else’s idea of success. If you’re the boss, you’re in charge.

Tell the truth about your financial needs

This is more than deciding what income will keep a roof over your head and food on the table, though that’s a great place to start. It’s important to have both a realistic budget for your lifestyle (what do you need and what would be even better?) and a realistic financial plan for your startup costs and first year in business. It’s important to know and work with your personal risk tolerance and your emotional needs as well. For example, I’m not motivated by financial stress and I feel better knowing I have a paycheck, so I built up a cash reserve and a side hustle before jumping into full-time self-employment.

Know what makes you tick

In today’s world of work, there are more opportunities than ever to be your own boss. You might be a contractor, a consultant, a freelancer, part of a collaborative team of professionals, a solopreneur. You might run an online business or launch a brick and mortar business. Think carefully about how and where you work best, what motivates you and what drains your energy—and design your new work life to match.

Align your strengths, skills and interests

You know the saying “Do what you love, love what you do”? That’s the opportunity presented to you when you start a business or design a portfolio of solo work. So take a good long look at what you love to do, what you’re great at and what comes naturally to you. Look at the skills, interests and roles that you’ve had in your professional life to date. Ask friends and colleagues for feedback. Use professional strengths and skills assessments. Once you’ve taken inventory, you can begin to see where what you have to offer is needed in the marketplace. How can you use that to creatively solve a problem that people are willing to pay to have solved?

Assess your personal resources

Moving from employee to entrepreneur often comes with changes and challenges. Do a gut check on what you are willing to adjust and not adjust. Be honest about any impacts on your family or your health. Identify the personal resources, character traits and supports you can draw on. Know what motivates you. Taking the time to do this homework is basically creating your own stress management kit before you need it.

Test out your idea

By now, you’ve got a good idea of what you might like to do. Refine it by going to the people or businesses you want to serve and testing the waters. If you have more than one idea, test one at a time, take on a couple of assignments or develop a quick-and-dirty version of your product of service. Do the market research on your field. Take it to the street and see what you learn.

Refine your business and marketing plan

A business plan doesn’t need to be complicated, unless you’re seeking capital, partners or other resources. You do, however, need some level of plan that identifies how you will bring in income, what your operating expenses will be and how you will get the word out to the marketplace. If you want a plan you can easily create and stick to, tailor it to the skills and strengths that you’ve already identified instead of using someone else’s model.

Map your transition

While it might be tempting to jump right in, that doesn’t work for many of us (and it can create a lot of unnecessary stress!). Instead, let’s go back to that vision you had in step one. How will you get from where you are right now to that one-year mark? What about the five-year mark? When you can identify the steps you need to take, when you’ll take them and how you’ll ensure your needs are met along the way, you’re already on your way to getting there.

About the Author Sally Anne Carroll

Sally Anne Carroll is a life/career coach for professionals and entrepreneurs who want to re-tool their work, define success on their own terms and design healthy, balanced lifestyles that match their strengths and priorities. She’s a freedom-focused advocate for helping clients reimagine, redefine and reinvent the status quo to achieve their personal vision of success and fulfillment. Sally splits her time between Portland, Oregon, and Christchurch, New Zealand. Visit her website to learn more and connect.

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