4 Boxes to Check Before Starting Your Solopreneur Journey

The following is adapted from The Aspiring Solopreneur: Your Business Startup Bible.

Once you’ve created a fully-built, kickass business plan and you’re ready to begin your solopreneur journey, there are four final boxes you need to check before you embark. The solopreneur’s life isn’t for everyone, so by taking the time now to run through this final checklist, you’re all but eliminating the possibility this isn’t the right fit for you.

Let’s dig into these four areas, starting with the most important: your lifestyle.

#1: Life Analysis

You have an idea about what the future commitment looks like, and how much time and money it will take to launch your solopreneur life. You’ve gone from theoretical to practical. Now it’s time to address if it’s going to be a good life fit.

Look at every element, including time, dollars, and especially personal accountability. You may need to spend 50 percent of your time doing business development and another 20 percent building the business and getting things ready before you even start actually doing billable work. That time is going to cost you money and it may take six-to-twelve months before you’re actually up and running.

Do you have enough funds in the bank? How long is your burn rate? Is your partner aligned with your decision? Is this within your comfort zone?

Once you start, it may take eighty-hour weeks for the first three to twelve months to get the business launched. You may be working for free or less money than you currently bring in at your place of employment. Do you feel that this is the best, highest use of your time? Are you leveraging your talents in the way that you really want to? What sort of treasure will it take to get where you want to be? Will the future returns be worth the investment today? If you have made it this far, I’m guessing it will be.

Be candid with yourself. If you know you are not a self-starter, you’ll need an accountability partner. Or perhaps you’ve determined it will take $100K runway to be comfortable for you to step away from your current position, and you only have $30K in the bank. Decide how or where you can save another $70K before you pull the trigger.

This can be frustrating but being frustrated is better than going bankrupt. Own that! It’s better to get frustrated and figure these things out now and make an educated decision.

#2: Business Analysis

Look at the business and the business plan you’ve built and ask yourself if starting this business is a no-brainer from the point of view of four different roles.

The investor. If your friend or family member handed you your exact business plan and financial viability and asked for $100K, would you, if you had it to give, feel comfortable offering the money based on his experience and effort? Is it safe? What return will you see on your investment? Is the risk worth it? Is this a no-brainer?

The manager. Is this something that is easy to manage, you’re able to do it, and you would find it fun? What is the market rate for this role, and can you afford to pay yourself in this capacity? Is this a no-brainer?

The head of business development. Seeing this business plan and knowing yourself, would you hire yourself to go out and bring in the volume of business you will need to be successful? Will you be successful at it? Is this a no-brainer?

The technician. Would you want to work for a business that looks like this? What should this position pay as an employee-technician? If you look at that dollar figure, would this be a company and job you’d want to work for? Is it a good fit? And will you ultimately enjoy all of this and will it fulfill your motivations? Is this a no-brainer?

Does this whole process sound like it will be fun? Are you enthused about acting as an investor, manager, head of business development, and a technician?

Life’s too short. Embrace the life you can have.

#3: The Path Forward

What does it look like when the choice is clearly to move forward as a solopreneur?

I once worked with an attorney who was employed at a large corporate firm where he charged his clients $400 per hour. Unfortunately, as with most large firms, the firm had a lot of expenses he had to contribute to, including travel, fancy offices, business development, sports tickets, sponsors, advertising, and marketing. The partners also received a share of his earnings, so he made far less than he charged.

He decided to explore going out on his own. He ran the numbers, did the analysis, spoke to advisors, gathered insurance quotes, looked at spaces, and assessed his financial viability. As part of his motivations he realized he loved patent law. He could do a great job being a small patent attorney and charge $300 per hour. It would allow him to transition into his own private practice with one office, and he could handle the work himself. He would be able to work 30 fewer hours a month, but actually increase his income and have the flexibility to spend more time with his family, which was important to him. He had no non-compete and great relationships with people in the community.

It was a no-brainer for him. If you do the research and assessments and realize that it’s kind of close, but it’s not quite there, then it’s not a no-brainer. And if it’s not a no-brainer, stop and assess what adjustments it would take to make it a no-brainer.

#4: Your Expectations

Some people fall in love with the idea of something in their head, but they’re not willing to see the reality of that idea’s implication. They don’t assess properly and instead charge full steam ahead. They think, This is my one shot. I’m never going to be able to do this again. PLEASE stop and know, that’s not true.

I’ve actually gone through this entire exercise and journey hundreds of times. Most of the time when I stopped and took a very hard look at the research, I came to the conclusion that it wasn’t a no-brainer. This is where you have to be protective of your time, of your investments, and really work toward your skillset. Review what you have, tweak it, adjust it, pivot, and if it looks like a win, dig back in.

It doesn’t mean that working for yourself as a solopreneur is completely off the table. Far from it. What it means is that the current direction that you looked at may not make sense. If you’re trying desperately to get this plan to succeed because you hate your job, or you hate your manager, and you dread getting out of bed, take a deep breath. Know that you have turned on some switches in your head that will expand your way of thinking. You will now start seeing opportunities everywhere. The more you cultivate and explore these opportunities, the more you’re going to grow and see what’s possible.

As you move ahead, you’ll start to have other business ideas or opportunities that appear on your radar. When you choose to not try and force a round peg into a square hole, that’s where you’re going to find success. Take the time to figure out the right niche that is your ideal fit, and you know you can excel, instead of forcing yourself into a niche where you’re unhappy or failing and going back into the same doom loop you currently work in. It may take you six months, a year, or even five years to find that niche, but it’s better to do than to hope a poor fit will work.

You may find a niche but need to hone your skillset before moving forward. Perhaps you need more education or a different direction. Will your current employer help pay for education? If so, that’s perfect. You get double the value for your time. You’re getting a paycheck, you’re contributing to your workplace, and you’re also sharpening the tools necessary for transition and building a plan to a solopreneur life at the same time.

What to Do Next

Now that you’ve examined these four areas—your life, your business, the path forward, and your expectations—what should you do next? If you hit a bump in a particular area, follow the suggestions in that section to see if you can eventually check that box.

If you went through all four and you know it’s a no-brainer, dive in and go for it!

For more advice on starting your solopreneur journey, you can find The Aspiring Solopreneur: Your Business Startup Bible on Amazon.

Kris Kluver is a seasoned solopreneur who started his first company at age nineteen in Omaha, Nebraska. Since then, he has been directly involved in the creation, operation, growth, and occasional sale of more than twenty successful businesses ranging from commercial real estate development and management to content marketing and daily social media operations. A former business broker and mentor, Kris has seen the inner workings of hundreds of businesses, some good, some ugly, all interesting. Through his many experiences he has gained a unique understanding, appreciation, and love of solopreneurship.


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