Are You Cut Out for Self-Employment?

by Jennifer Miller on February 22, 2012

in Business Management, Workplace Issues

In 1995 I started the consulting company SkillSource. Early on I made the strategic decision to function as a home-based solopreneur, meaning I am the primary service provider. When projects require it, I sub-contract out training delivery and consulting services.  For the administrative side of my business, I make use of a cadre of skilled professionals: web designer, tax accountant, my virtual assistant Suzie and so on.

For me, it’s been a fantastic career choice. But it’s not everyone’s cup of tea. Over the years, I’ve met many talented colleagues who have taken the plunge into self-employment for awhile, only to be lured back into working for a larger, more established organization.

So why do some people love being out on their own, while others prefer working for The Man?

Beyond the practical considerations such as start-up capital and paying for one’s own benefits, there’s a whole other facet to determining your self-employment viability: does it fit your temperament? Take my unscientific quiz to see if you’re suited for running a home-based business:

  1. Are you comfortable working for long stretches by yourself?
  2. Can you make tough decisions without the input of many people?
  3. Are you a focused person?
  4. Do you have an established network of service providers to whom you can turn for assistance?
  5. Do you have the patience to teach yourself how to do things—especially mundane things like how to fix a broken printer?
  6. Have you ever worked for a small company (less than 25 employees)?
  7. Do you like to sell?

How did you do?

My (unscientific) analysis: if you enthusiastically answered “Yes!” to at least five* of the questions above, in my opinion, you are suited to the life of a solopreneur.

Here’s my rationale:

Questions 1-3 address the solitary nature of self-employment. If you are the type of person who needs the energy of other people to be productive, self-employment may not be a good fit for you.

Questions 4 and 5 speak to the need for solopreneurs to be do-it-yourselfers. You don’t need to do everything yourself, but you do need to know where to find people (at a reasonable price) who can help you.

A “yes” to question 6 means that you’re already familiar with how to wear many hats. Small businesses don’t have huge budgets or large staffs, so everyone needs to pitch in. This will serve you well if you go out on your own.

* A “no” answer to question 7 is a deal breaker. If you’re going to go it alone, you’ll need to learn to sell. If you’re like me, you may never learn to love it, but it’s a vital part of keeping your cash flow going. If the thought of making phone calls and networking with strangers breaks you out into hives, then you might want to re-think your path to self-employment.

That’s my two cents’ worth on how to decide if self-employment is for you.


Now, it’s your turn.  I’d love to hear from other solo business people—

What are the key factors that you think determine a solopreneur’s success?


{ 2 comments… read them below or add one }

Craig Juengling February 22, 2012 at 6:01 pm

Jennifer, can’t help but like this post. I took my plunge about 15 months ago. I love it but chasing your next meal ticket every day ( see #7 above) eliminates the weak hearted. How about one more: #8 Do you have the ability to work brutally long hours for weeks on end because you can’t turn down good customers… only to experience not having enough business six weeks later? Feast or famine.

As always, well done.


Jennifer Miller February 23, 2012 at 7:40 pm


I agree with your addition of #8.It is indeed feast or famine. A word of encouragement to you: 15 months is still a fairly new business. As your client list grows, so will the referrals. The peaks and valleys will smooth out a bit. When that happens you’ll gain confidence in knowing that another project will surface, as long as you kept up your marketing efforts.

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