Photo Credit: Garrhet Sampson,
Photo Credit: Garrhet Sampson,

The Conversation Started Like This….

Like most other holidays, my family gathers together to eat way too much delicious food and catch up with all the goings on in each other’s lives. This holiday was no exception. I had an interesting conversation over the Canadian Thanksgiving Holiday with some family. All of them are or were at one time, in middle management or independent business owners.

Specifically, my sister asked, “Lisa, I see all the work you do with leadership, but it seems like it applies only to those working for other people. How does leadership apply to people who are solopreneurs?” My sister’s a hairstylist who owns her own business inside of an established salon. I thought about her question, asked her and other family about their experiences and decided to do some research.

About The Solopreneur…

First, let me clarify what’s meant by “solopreneur.” It does have a slightly different nuance than an entrepreneur in that the solopreneur works completely alone. Very rarely do solopreneurs have a tribe of partners, employees, contractors, or friends that support the business.

They’re the master of their craft and are responsible for every aspect of their business from the production of their product or service to the accounting of all dollars coming in and out of the business. EVERY responsibility falls squarely on the shoulders of the ONE solopreneur.

By contrast, the entrepreneur usually has a tribe of people to support the various aspects of his/her business and while the entrepreneur may have times where they work completely alone, in general, they have support of contractors or network contacts when needed.


So what’s the appeal to being a solopreneur? Tippetts indicated that the greatest attraction to working completely independent is flexibility. He explained that as a solopreneur, you have the ability to basically work any time or any where.

You’re essentially not confined by set work hours or an office desk. That being said, it’s also seen as a way to have greater freedom over the choices that are being made, the direction of the business, or the creative license one takes to try new things. You can choose the clients you work with and the jobs you’re willing to take. Tippetts admits, however, that there are some definite downsides to this kind of work; loneliness, competition, and work/life balance.


Ivan Wadjaya shared some of the same downsides to this career choice. Loneliness in the face of real business challenges can be tough. There really isn’t someone else to lean on when “it” hits the fan, because chances are that your network would also be your competition. Additionally, when the work starts to pile up, there’s no one to delegate to. You just have to dig in. Competition’s also tough.

There are likely several solopreneurs out there already doing what you’re doing. Some who are more skilled, some more disciplined, some better at marketing, etc. Differentiating yourself isn’t easy, it will take time to get your own slice of the market pie.

Customers need to see you as offering something different from the next guy doing the same thing you do. The competition isn’t going away and marketing your business is all on you.

Lastly, being a solopreneur can be financially difficult. The economy’s fickle and ever changing. Oftentimes, you’ll have to produce without expecting anything in return. And then…there are the customers that just don’t pay. Then it’s up to you to determine if you have the finances to pursue legal recourse. Oftentimes, it’s just not worth it financially or emotionally.

How does leadership apply to the solopreneur?

Well…it starts with expanding the definition of leadership.

The online Meriamm-Webster Dictionary defines leadership as the following: 1) a position as a leader of a group, organization, etc.; 2) the time when a person holds the position of leader; 3) the power or ability to lead other people.

I’d suggest that it requires a TREMENDOUS amount of “self-directed leadership” to be a successful solopreneur. Here’s where I see the connection:

  • Motivation-you must continually motivate yourself to greatness, especially when times get tough.
  • Routines– these are practices that help you optimize your time and your productivity.
  • Wellness strategies– mindfulness, meditation, diet, and exercise are critical to maintaining your health.
  • Time management– this becomes critical in order to preserve a work/life balance.
  • Strategic plans– planning your big vision and the steps required to get there are necessary for any kind of success.
  • Growing skills– continual reading, upgrading, learning, seminars, and training courses are needed to stay ahead of your competition and refine your craft.
  • Leadership energetics– this is the fundamental need to be a high-vibe solopreneur that brings clients in droves and success beyond expectations.
  • Communication-obviously you need to get the word out about who you are and what you do. Your message, branding, and marketing all need to be clear, concise, and in alignment.
  • Relationships– while maybe you don’t have to work with employees, you do have to work with clients, and relationship skills, rapport-building, and networking are all part of it.
  • Coaching– this is particularly critical in the beginning, when you’re first trying to establish yourself. A great coach can help you with the areas you are unsure of, acting as your sounding board when you run into difficulties, and help you redirect your energy to results based success.

When I look at this list, there’s not much (if any) difference between the needs of a leader in a company/business and the needs of a solopreneur. While the circumstance of each work scenario may be quite different, the actual needs of the INDIVIDUAL are essentially the same.

This thanksgiving, I’m grateful to my family for a thought-provoking question and the interest they show in my leadership journey. I think what I’ve come to realize is that leadership is an individual, internal journey regardless of where or how you choose to work. And…that’s where we’re all connected…at the core passion that gets us up each day.

Really, we’re all leaders. What do you think?