Office for One“A chair is still a chair. Even when there’s no one sitting there”

Burt Bacharach/Hal David – Promises, Promises (1968)


When you take a leap of faith and promise yourself to start the business of your dreams, an empty chair in an Office For One symbolizes two things.

The first is that you’re now the captain of a new ship about to take its maiden voyage. There’s no boss looking over your shoulder, no cubicle mates to gossip with at the water cooler, no time-clock to punch. You’re free to chart your own course, drop anchor in any port of call that looks interesting, and decide how to spend whatever treasure you might discover along the way. That chair represents an end to over-stuffed committees, snore-fest staff meetings, annual performance reviews, and snarky office politics…and the beginning of a fasten-your-seatbelt adventure in which every risk and every reward will carry your signature style. It’s the place where you’ll imagine, you’ll plan, you’ll create, you’ll reinvent. If it’s comfortable, you may even take occasional naps in it with no worries of censure or interruptions, for you’ll know that you – and you alone – have earned the right to sit there as long as you want.

Not every aspect of an empty chair is quite so welcoming, however. Depending on how many years you spent being an employee of someone else, there’s a possibility that all of the things you couldn’t wait to get away from are among the first things you’ll miss when you become your own boss. The organizational structure, rules and deadlines that previously allowed you to multi-task with gusto from 9 to 5 are no longer part of your daily routine, a dramatic shift that – in the absence of self-discipline – can lead to binge-watching multiple seasons of TV shows, playing computer games, and spending way too much time on email. The lines between your professional life and your personal life can become blurred, especially if they co-exist 24/7 under the same roof. Calling in sick to play hooky isn’t what it used to be, either, nor can you delegate tasks and errands when you’re caught in a crunch.

As the saying goes, it’s lonely at the top.

It can be incredibly lonely sitting in that chair, too.


The idea for this book came from the observation that although there was a bounty of titles on the market targeted to small businesses, none of them were addressing the unique wants and needs of the smallest business of all – the sole proprietor. Likewise, my colleagues and I were spending lots of money – and valuable time – on small business workshops which assume that the participants have actual employees. Topics such as “How to Motivate Your Team” (uh – what team?), “How To Choose the Best Payroll Company” (uh – I’m only paying one person: Me) and “How to Resolve Personnel Conflicts” (uh – me, myself and I get along quite well) didn’t apply to the day-to-day challenges of managing a micro-enterprise.

To add insult to injury, many chambers of commerce across the country don’t have a “sole proprietor” designation when one applies for membership to take advantage of local resource and networking opportunities. If you choose not to label yourself as a small business owner, the only other choices are “Work From Home” (i.e., telemarketing, recruiting, affiliate sales, bookkeeping, or being a virtual assistant to a remote employer) or “Home-Based” (i.e., arts/crafts, piano lessons, daycare for children or pets). But what if you’re an independent consultant, decorator, writer, graphic designer, personal trainer, tax preparer, therapist or videographer? Clearly you don’t fit into either of these chamber of commerce categories. Further, “home-based” often carries a negative connotation that you’re more of a casual hobbyist than a driven professional or that you’re woefully unsociable and can’t function in a “normal” workplace like everyone else.

Let’s face facts. Not every personality, lifestyle or biological rhythm is well suited to conventional 9-5 employment. Maybe you’re someone who hits your best stride after the sun goes down, loses all track of time when you’re energized doing something you love, or just hates the tedium of always having to get group consensus before moving forward on even the most minor decisions. Maybe you’re someone who yearns for a portable career that can go anywhere in the world that you do, or one that allows you to ditch a stressful daily commute, work from the comfort of your own house and spend more time with those you love. Maybe you even see this leap of faith as a preemptive measure stemming from the angst of becoming jobless as a result of your employer downsizing, outsourcing, merging or going bankrupt.

While enrollment in entrepreneurship programs is currently high among millennials, the youthful enthusiasm to start a business from scratch is often tempered by risk aversion, corporate “Goliath” consolidations that make small start-ups nervous about competition, shifts in government regulation and yes, the ever-daunting onus of repaying student loans. For entrepreneurs whose college years are long past, there are considerations such as raising offspring, supporting their educational pursuits, managing a mortgage, and staying healthy – all of which impact one’s ability to consistently bring in an income that will keep the bills paid.

Still reading? Good. Let’s start with some critical questions to determine if you’re truly up for the challenges ahead.

  • What are the top three reasons you want to be in business for yourself? (Be honest!)
  • What are the top three skill sets you possess that you believe best position you to be your own boss?
  • Will your proposed business sell products, services or a combination?
  • Who do you believe needs these products and services (and why)?
  • Who else is already delivering these products and services and what do you think distinguishes your own approach as an up-and-coming competitor?
  • Is your education and work experience sufficient to run this business or do you need to take classes or acquire special licenses/certifications/permits?
  • Could your business idea initially be launched part-time to test the waters?
  • Is your business concept sustainable?
  • What is your exit strategy?

The last question in this list pertains just as much to what you’re going to do if things don’t work out (looking for a new job or trying to go back to your old one) as it does to planning for your company’s future growth. Will it one day reach the point that you’ll want to diversify your product line? Incorporate new services? Enter into a partnership? Start hiring employees? Cross “starting my own business” off your bucket list and go do something completely different?

One of the elements that many sole proprietors fail to take into consideration is whether their business model is realistically “scalable” to their personal investment of time and interest. As an example, my husband and I many years ago discovered a charming shop along the Royal Mile in Edinburgh that was run by a woman who loved to knit. The shelves and racks were filled with custom designed sweaters, scarves, caps and gloves that she had made entirely by herself. She related how many customers told her that she could reach more people if she just set up a website and sold her merchandise online. While she had no doubts her designs would find an eager following, she confessed to us in her thick Scottish brogue that she only had but the ten fingers and unless she could teach her toes to “wheedle the needles,” there’d be no way she could keep up with the demand.

She also pointed out that a lot of the joy she derived from her craft was simply talking to the people who came in to buy something from her.

And that brings us to what is the final and most important aspect of this bold new journey you’re contemplating. If you become so preoccupied with your own screen – a definite hazard if your sole proprietorship exists only in cyberspace – you can all too easily forget how to promote the necessary growth levels that come from in-person connectivity.

So get out of that chair. Have lunch with a friend. Take a long walk with the dog. Go see what’s new and going on in a world that keeps spinning whether you’re working or not.

Don’t worry. Your chair will still be waiting for you when you get back.


To purchase Office for One: The Sole Proprietor’s Survival Guide, go to For information about discount copies, feel free to contact me directly at



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