On your mark...get set...

Major life changes are rarely a one-and-done process. The obvious dividing lines that define our lives, like graduation, marriage, or promotion, aren't isolated happenings. They're the result of a series of decisions we made or actions we pursued.

Once we cross a major threshold in life, we may not always know what lies ahead. But isn't that part of the challenge life offers us?

The idea of self-employment is something that many of us will consider at some point in our working life. When colleagues reach out to me about starting a business, the conversation usually starts with what that person doesn't have or doesn't know.

I often hear, "I've never started a business before. I love the idea but wouldn't know what to do." Another question I hear is, "Working for myself sounds great, but what if I went bankrupt? How would I know when it's time to stop?"

If you can go from a very broad idea to bankruptcy in one sentence, then you probably shouldn't quit your day job just yet. It might be more helpful to stop thinking about all the things that could derail you in the future, and start thinking about what's holding you back from ever getting started.

The Either/Or Fallacy

Nobody goes from entrepreneurial novice to successful businessperson in a single step.

Not every innovation will be rewarded. Today's great tech idea is superseded by tomorrow's new killer app. The CEO whose name was in every headline turns out to be not so much of a genius. That can't-fail business just announced they will cease operations next quarter.

Many entrepreneurs have made the journey to self-employment through a series of smaller steps. A talented craftsperson might sell their products from an online shop while continuing paid employment elsewhere. A part-time worker could take on freelance work to gain experience while learning how to market their skills, deal with customers, and manage finances.

I got my first freelance gig from a former boss who needed someone to write a financial course for her company. She gave me a budget range and I quoted a price at the top of her scale. I probably put in more hours on that one project than on anything else I've ever done. When it was time for my initial presentation, I came up with four different approaches, just to make sure I covered every detail the client could possibly want.

The contact my boss introduced me to liked all of my ideas and asked me to map each one out a bit more so they could make a final decision. My overachiever gene kicked in and I built course maps, a full lesson plan, slideshow, and instructor notes for each approach. Who knew freelancing could be so much more work, I asked myself.

A few days later my former boss called to tell me that I'd offered too many choices. "My team can't get started because everyone wants something different, but I want them all teaching the same class. Which one do we go with?," she asked.

I froze up, fearing that choosing one would mean that I didn't have confidence in any of the others. "Well....," I started.

"Look, we've got to get everyone trained on this today," she said. "If you were teaching the class, which one would you go with?"

"Option number two," I said, picking a number out of thin air. That must have been a winner, because they paid me a week later then hired me for another project.

The second time around I cut my workload by 75% by offering one idea and creating one set of materials. The client was happy, and I learned that it was more important to come up with one good solution that resolves a big need than to anticipate and resolve every possible problem ahead of time.

Finding Your Personal Starting Line

You don't have to uncover and answer question about why you have (or have not) moved forward on your dream of self-employment. Instead, try to understand what self-employment means to you. Think about your own motivations, expectations, and possible distractions.

Start by creating a table of issues and answers. At the top of a page, write a single question: What is one specific thing holding me back from starting to work for myself? Underneath this, add two columns. Label the left side column Issue and the right side column Resolution.

Ask yourself the question then decide the single largest hurdle that is holding you back. Write down whatever feels like the biggest roadblock then ask yourself the question again. And again. Continue to ask the question until you have noted all of the reasons you can think of.

The point of this exercise is to articulate real concerns, not to judge yourself. This is your information gathering stage; you don't need to come up with any resolutions yet.

Build two more tables and ask yourself these questions:

• What does self-employment mean to me? Do you hope to earn supplemental income while you keep your current career? Do you want to be a solopreneur or hire others to work for you? Do you hope to work for yourself for many years, or for a shorter length of time?
• How will I know when I'm ready to self-employ or start a business? What's the tipping point where you'd feel confident enough to act on your dream? How much professional or economic risk are you able to tolerate? What specific knowledge or skills do you think would help you launch and sustain self-employment?

You don't have to answer all three questions in a single sitting. Let the questions percolate in your mind for a week or two. Write down answers as they come to you.

After a few weeks, sit down and look at the issues you noted. Then consider any reasonable actions you can take to resolve your issues. Can you find a mentor to help you? Sign on with a contracting agency to get short-term jobs in your field? Learn new technology? Join a professional association to grow your contacts?

Successful entrepreneurs focus their efforts in the sweet spot that exists where their skills and interests align with the needs that clients or customers will pay for. That intersection - that niche - is your starting point.

And only you will know when you're ready to step through it to begin your true entrepreneurial journey.