Could self-employment be the right path for you?

Editor’s Note: This is the first of 12 columns on starting a business that will appear in the next 12 months – one each on the second Sunday of the month, from September through August. Last year’s Second Sunday Series focused on readers’ questions, while preceding series highlighted career building during recovery from addiction; work in the trades; and career issues of special concern to millennials and mid-career workers.

Have you ever considered starting a business?

The concept of business startup used to be simpler. Not the process, mind you, but the principle of it. In years past, if you were going into business for yourself, you were likely going to do/be something right out of “central casting,” as they say.

Maybe you’d open a main street shop, or perhaps you’d hang out your shingle as an attorney or start a barbershop. If your business was going to be a behemoth, that would happen decades later, after generations of your heirs had taken a turn at building on the growth achieved by their parents and grandparents.

Today when we talk about starting a business, the umbrella expands to include solo gigs, investment-funded tech startups, global service providers, poets who sell their work online, Airbnb operators, and side-hustling web designers, among others.

This isn’t wrong, per se, but it is a bit sloppy to use the same term for such a broad range and style of activities. The same issue exists when describing the person who starts the venture. Is that an entrepreneur? A solo-preneur? Or simply a person who is self-employed?

Luckily, the main issue isn’t what to call yourself, but what to do with yourself. Unlike stepping into a role as someone else’s employee, working for yourself is a job without boundaries. Setting those boundaries means deciding your own reasons for going into self-employment and then ensuring you reach those goals.

It could be that you just need a bridge between jobs, or that you want to use the self-employment to elevate your status and experience so you can get a better job later. Or perhaps you want to exit the formal work world permanently, using your business as a way to call your own shots. You might want to craft a lifestyle-business that lets you work from anywhere, on your own terms. Or, of course, you could be planning to make serious money from your business, by growing and then selling it.

If you’re considering any version of self-employment, your first step is to figure out why. The answer to that question will drive all the decisions that follow, from whether to have employees to how much money you need to gross each year to meet your goals.

Starting a business is the subject for my Second

Sunday Series this year, which means that every month for the next 12, I’ll be devoting the second Sunday to a topic related to self-employment or business startup.

It’s not an orderly process, but I’ll attempt to tackle this unwieldy topic in an orderly way, with columns focused on the main steps and decisions related to launching out on your own. If you’d like to follow along in the series each month, you might find it helpful to keep a journal of your own steps.

For instance, here are some challenge questions to consider related to self-employment:

■ What appeals to you the most about working for yourself ?

■ What’s the most uncomfortable or frightening?

■ Why would you want to do this?

■ Do you have an end goal for a business you might start?

■ What kind of daily life do you envision as a business owner? How many hours are you working, for example?

I’d like to hear your ideas, questions, resources and experiences around this issue, whether you’re in business for yourself or you’re just starting to explore your options. I’ll try to incorporate as many views as I can into the monthly columns. Meet me back here in October and we’ll continue the conversation.