Ready to Work for Yourself? | A Self-Assessment for Solopreneurs

It’s tempting and doable. All we need is an idea and, virtually overnight, we can launch our own business. But should we? 

An entrepreneur is someone who, by definition, “organizes, operates, and assumes the risk for a business venture.” Interestingly, The American Heritage Dictionary 4th edition doesn’t have an entry for “solopreneur.” That surprised me since the term is widely used for individuals, like me, who are their businesses.

 Ready to go solo? 

I did—four times—and sometimes with two at the same time: (Egad!) 

  • Lennon Management Associates—specializing in veterinary practice management consulting (5 years)
  • Holly Run Farm, Inc.—race and show horse breeding, racing/showing, and sales (20 years)
  • Special Collections for Horsemen—equine art, antiques, and collectibles sales (10 years)
  • Big Picture Consulting—career and business coaching for individuals and small businesses (the remaining one, 2002-present) 

I knew nothing about owning a business before I started. Each venture was an education on how small business works. Those were the easy lessons. 

The real challenge was learning how to be in business by myself.   

Most of us who start solo businesses are focused on the “fun stuff.” We figure we’ll just announce our offerings and customers/clients will start calling. When they do, we’ll eagerly deliver our advice, services, or products. How complicated can it be? It’s just us doing what we do best. 

Well, as the line goes, if owning your own business were so easy, everyone would be doing it. 

Whether you plan to walk away from a steady job or keep it for a while (I was glad I waited) to start your solo business, take time for this self-assessment. It’s not all the questions you should ask but a good start. 

A Self-Assessment for Solopreneurs 

After each question, write your answers in clear detail. (Wishful thinking doesn’t cut it!) 

Business Planning 

  • What services and/or products will I offer at launch?
  • Who is my target market? What will they pay?
  • How will I contend with my competitors?
  • Am I business fit? Do I have the business skills and knowledge I need for:
    • Goal-setting, tracking, and performance analysis
    • Sales and marketing
    • Customer service, problem solving, troubleshooting
    • Recording keeping—financials, files, client/customer accounts, vendor agreements
    • Communications, planning, organizing, priority setting
    • Social media tools, outlets, and channels
  • How much revenue must the business generate to cover my business expenses and support me? By when?
  • Is it more prudent to start this business as a sidelight or just go for it?
  • Do I have enough money to invest to get off to a good start?
  • What’s my fallback position if the business isn’t successful?  


  •  Why am I doing this?
  • Do I have the personal discipline to manage every workday effectively, including the ability to:
    • Stay focused on priority work, not procrastinating?
    • Develop/improve/deliver services and products?
    • Make calls and meet with prospects?
    • Handle administrative details?
  • How will I handle disappointments? Success?
  • How much alone time can I tolerate and still be productive/happy?
  • What do I want from the business—money, personal growth, satisfaction, independence?
  • Who is my professional team (i.e, accountant, IT support, VA, attorney)?
  • Who is my support system—other entrepreneurs, mastermind group, confidants? 

Don’t let your missteps get you down.

Each of my businesses brought in plenty of revenue but only the current one is truly profitable. When you ask a solopreneur how s/he’s doing, most will say “great,” although that may not mean profitable or even happy. So please don’t measure yourself against success illusions others put out there. 

It’s important to start your business with boundless optimism: That’s what helps you slog through the bad times. Reality can quickly take the shine off a dream, but hard work and perseverance can restore it. Being a solopreneur can be a great ride.  So hold on and feel the energy.  

How about taking some time this week to complete that self-assessment? Or share it with an entrepreneurial friend.  It may be just what you need.

20 thoughts on “Ready to Work for Yourself? | A Self-Assessment for Solopreneurs

  1. Great post. I am feeling like the shine has come off of my biz for quite some time now! what with lowered reimbursements and rising rent, electricity, etc.
    I have alot of projects going at once, and I know they will pay off , but it is a slow going! I know slow & steady wins the race!
    We have something in common! I used to work on the racetrack as a hot-walker/exercise rider….many many years ago, when I was 19.
    We owned pleasure horses for 12 years, alas they passed away. I miss them terribly, altho I dont have much time anymore! I work alot!

    • It happens with every business. They develop a kind of rhythm of their own, sometimes it’s seasonal, other times economic. It’s key to do what you’re doing…using the flat times to develop new initiatives, reconnect/connect with prospects and referrers, and look at costs. What’s difficult about being on your own is that you have to be your own optimism stoker. The hard truth is that with solopreneurs, no one has a real-time stake in your success or failure. We may have family and friends who support and root for us, but the business is always about us. That’s why having a group of other solopreneurs, preferably in other lines of work, as a support system to share our inner struggles can be a big help.

      Well, how about you being a track rider! What a great opportunity and experience. You must have been very good with and on horses, as that’s not a job for the timid or the unaccomplished. The TB’s I rode were show horses; the one’s I bred to race were left to trainers and jockeys. I knew my limits. I only have one old horse left–a 28 yo retired QH track pony–a big pet. When he’s gone, I’ll be in a quandary. I really loved having the foals around. So I understand your missing them. I live on my farm, so there’s plenty of work, just not plenty of horse work. Thanks for sharing that…brought back memories! ~Dawn

  2. Thanks, Cherry, for a very thoughtful post. I am in the midst of a life transition after years of academia and being a Full Professor, so this is very timely. My biggest challenge is liking the fun and creative stuff and not the daily maintenance and organization as much. The multitasking demands are huge, especially being a mom as well. A second challenge is taking on too much as I’m doing practice, blogging, and starting a book proposal, all after moving to a new area where I don’t know anyone. I think I thought it would be profitable much quicker as well. Yet I’m happy doing this as it really is mindful self-expression and a way to express my own creativity and what I want to contribute to the world.

    • You have a lot on your plate, Melanie, and I understand what a cultural shift this must be in your worklife. Academia and entrepreneurism are apples and oranges. That said, transferable skills come in pretty handy during a transition along with the willingness to dig in and go for it.

      Everything happens when it’s supposed to. Our challenge is not to use ourselves up beforehand. It really is all about meeting priorities–ours. The hard part is resisting the desire to meet the expectations of others when they don’t fit our business plan, needs, and commitments. For what it’s worth, it took me a good three years before I had a clear idea what I wanted my business to be and how I wanted it to work for me. Until I got that clarity, I just tried things, eliminating what I didn’t like (even if it brought in good revenue) and keeping what I did. Like you, I wanted my business to be a healthy outlet for myself so I could help my clients enjoy success and relief from their challenges.

      Thanks for taking the time to comment. I’m looking forward to sharing lots of great insights with you going forward. ~Dawn

  3. I read the title and knew I was going to like this post! Then when I got to “We figure we’ll just announce our offerings and customers/clients will start calling. When they do, we’ll eagerly deliver our advice, services, or products.” Now you’ve really got my attention! This was exactly how I started out as a Realtor….hmm people just don’t pick up the phone, call your office and bingo you have a client to work with? Talk about being in shock. What went through my head that first year wasn’t “Why am I doing this?” It was, What was I thinking??

    Many people may not view Real Estate Licensees as Solopreneurs, but we definitely are and not being prepared for that is the first big “misstep” that Will get you down and possibly knock you out.

    What a great Self-Assessment list, Dawn! You have an incredible way of taking the complicated and making it seem as simple as following a recipe. I’m planning on following your advice by taking the self-assessment and then working on the restoration process. Thank you for this incredibly helpful and encouraging proposal. ~Pam

    • This is a great reminder to lots of people who are solopreneurs but don’t look it from the outside, like realtors, yes. And also some insurance salespeople, financial advisors, travel agents, and anyone who works solely on commission. Somehow when people like you align with a company but really work as an independent contractor, the outside world and even you yourself forget you’re on your own. That means many, if not all, of the requirements of owning your own business apply. In some ways, you have many other challenges unique to your situation.

      Thanks so much for bringing this to light. I’m really glad the post resonated with you and that perhaps the self-assessment will be helpful. I really appreciate all the affirmations you give me and will continue to try to live up to them. Stay well, ~Dawn

  4. Great checklist Dawn,
    The question about how to manage disappointments (and success), caught my immediate interest. As a solo entrepreneur having a support system is essential. It is also important to have a realistic plan; knowing ideal client and build relationship, have a product that fits the client and a way to catch the client’s interest.
    A positive attitude – never give up, but learn from mis-takes – is extremely important and go hand in hand with work discipline to create a momentum of steady progress.
    I am just starting out and learning from mistakes. If I did not love blogging, I don’t know how I would keep going!

    • You are so right, Irene, about the importance of a positive attitude. When things look bleak, we need to tap into our essential positive nature to get through it. That network of good relationships is always a huge lift too when we need to lean on it. The beauty of blogging is the feedback and the energy that we get from the affirmations and insights others share with us. It certainly has been an amazing experience for me and I am grateful for all the people who find value in what I write. ~Dawn

  5. Wonderful points and checklist, Dawn. It requires so much disciplineto run your own biz (and you have 4–ugh!). I feel that I made the right decision for my growing venture, but it takes a ton of energy, belief in yourself, and skills that will set you apart.

    I agree with Irene-it is so important to have a support network. Either “en vivo” or virtual. And Pam’s right 0n comment about making your info simple to follow like a recipe–delicious!

    Thanks for the solopreneur reinforcement:)

    • Yes, it sure does take discipline. The fact is that I only have one business going right now and I intend to keep it that way. My coaching and consulting practice keeps me hopping along at exactly the pace I prefer. I do miss the horse breeding, but so long as I have one or two here to keep me schlepping around, I’m happy.

      Business growth does take tremendous effort and risk tolerance. So kudos to you for having the will and courage to do it. Growth is how we continue to exercise our business creativity and helps us not to get stale. When you have a good core of professional colleagues to confer with, it infuses energy. I wish I could turn it my career advice into a recipe, but too often we’d end up with more shepherds pie than any of us has a taste for! Great to here from you. Solopreneurs unite! ~Dawn

  6. Great post. I remember being so excited about all of the stuff you mentioned. I knew I’d have to work hard (and long hours) to make the business successful, but I had no idea about all of the anxiety over the ups and downs… It really is critical to have a support network to get you through the tough times and cheer you on to the good times.

    • Oh, for the love of anxiety! Yes, that’s the worst part. It’s the waking up in the middle of the night with your mind racing, trying to subconsciously solve about some problem. It’s worrying about whether or not a client is taking the right action, satisfied with your service, or saying good things about you. It’s concern over cash flow, expense management, and having enough work in the pipeline. That’s why solopreneurism isn’t for everyone. It takes a deep commitment to the work you want to do, the belief that you can make it successful, and plain old guts! That’s why we need the support network you so clearly laud to keep us going. Keep the faith! ~Dawn

  7. Great post. I think once you get the bug it’s hard to ever go back. I think I officially knew I was where I was meant to be after reliving entering a corporate job. It was amazing how much I’d changed and how, while the dream was very realistic and some of it was exciting (coworkers again! cube chats and office gossip!) I basically woke up feeling like it was a living nightmare.

    I think what has surprised me the most is how much an act of faith (of skill, ability, passion) this small biz stuff really is. I feel MORE connected to small business owners after going through my ongoing emotional rollercoaster, ups, downs, failures, successes.

    I hope people read the checklist and take it seriously!

    • What a great testimonial, Elizabeth. You’re right, sometimes it takes “going back” to realize that our steps “forward” were the right ones. Getting paid regularly, like passing “go” in Monopoly, is certainly easier on the nerves than attracting and retaining work from good paying clients/customers. Owning your own business is not for everyone but it still challenges the ones who have it in them. Thanks, ~Dawn

  8. Great post, Dawn! I’ve been working solo since 2005 but need to redo pieces of my “vision” due to recent changes in the marketplace…I’ll be doing your checklist! I knew going into private practice that it would be much more like running a business than I was prepared for, and I was STILL surprised at the business aspect of it. One day at a time…

    • Yes, this small business thing is a moving target and it takes courage to decide that we routinely need to make changes, sometimes in directions that we’ve avoided for any number of reasons. Our solo work challenges our comfort levels all the time, so kudos to you for having the wisdom to see that some “vision” pieces need to be revisited. I hope the checklist helps surface the right aha moments and makes your next steps easier. Yes, one day at a time! Thanks so much for commenting. ~Dawn

  9. Great post and checklist Dawn. It’s the risk tolerance part that makes me hesitate and start things on the side versus full blown effort, but even with “side businesses” this checklist is dead on. I will share with hubby since he’s starting a construction business (theoretically). 😉 He needs a little confidence boosting…

    • So glad the checklist seems helpful. See, it’s that thought-leadership stuff at work again! :-) Yes, risk tolerance is a big issue. It can be both asset and liability. That’s why being in business for ourselves is so challenging. Not everyone has the stomach for it. It seems that entrpreneurship is a family trait in your household. What fun! ~Dawn

Leave a Reply