Forks In the Road for Solopreneurs

I‘ve been thinking about the forks in the road that we face in our solopreneur lives.

Some of the forks are big ones, and making the wrong choice can have huge ramifications for our businesses. For example, should I quit my job — or not?

Other forks are small, and there isn’t a right or wrong answer — for example, using Webtype or Typekit for a font service.

Here’s an extremely partial list of questions that we face. (To help you make your decisions, click here for a post about the eight decision-making perspectives.)
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Why I Moved My WordPress Website to Rainmaker

This week I’m rolling out a new design for It’s actually more than a new design. It’s a complete website overhaul: the exterior, the interior, a total engine replacement, new tires, new brakes, and new shocks. The only things left unchanged are the paint colors.

This is a bittersweet moment. I’m fond of the original website, which debuted in March 2010. It served me well. I’ll miss it, and I know you probably will, too. (But we can gaze upon the old site whenever we want via the magic of The Wayback Machine).

So why did I overhaul my WordPress website and move it to Copyblogger Media’s new platform, Rainmaker? Read on.
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Your Business is an Accident Waiting to Happen, If You Don’t Do This

This morning my 16-year-old daughter Anna took the road test for getting her driver’s license. It was a bad day to drive, let alone take a driving test — overnight we received 4 inches of snow, which means we now have more than 3 feet of snow on the ground.

Anna and I arrived at 8:25 a.m. at the Department of Motor Vehicles office, which is located in the National Guard armory in Owatonna. Anna and the instructor left the office for the driving test at 8:38 a.m.

I sat in the armory hallway, nervously waiting for them to return. I sent a text to my wife:

“I have no idea if she’s going to pass. I’m going to guess she doesn’t. Hope I’m wrong.”

My wife: “Not pass because of the roads?”

Me: “Yes. The roads will make it a challenge.”

The instructor returned after about 20 minutes.

He stopped and said to me, “She did really well with observation. Even at a green light, she looked both ways in the intersection to see if there was traffic. Observation is more important than the maneuvers or anything else.”

“Really? That’s great…Did she pass?”

Observation vs. Maneuvers

Right now, 8 hours after Anna’s driving test, I’m pondering the instructor’s comment: “observation is more important than maneuvers.”

Is that also true for the solopreneur life?

Let’s look at the definition of observe: “to watch and sometimes also listen to (someone or something) carefully.” In your solo business, careful observation means knowing client (or customer) ambitions, goals, needs, fears. Observation often takes the form of research. Observation requires that you ask the right questions and listen carefully to the answers.

The maneuvers of solo entrepreneurship are things we do with our skills: writing ads, making presentations to prospective clients, planning product launches. All those things are important, but careful observation is the foundation for success.

It’s through careful observation that we begin to form strategies and decide tactics. If we don’t take time to observe, then our business maneuvers might as well be done in the dark, because their only chance at success will be pure luck.

And yes, Anna passed her driving test.

Think for Yourself

There’s a short passage in the book “Moneyball” that can be paraphrased and applied to solopreneurship.

Think for yourself along rational lines. Hypothesize, test against the evidence, never accept that a question has been answered as well as it ever will be. Don’t believe a thing is true just because some famous businessperson says it is true.

That’s the essence of successful solopreneurship. But don’t take my word for it.

21 Things We Love and Hate About Being Solopreneurs (in GIFs)

In a typical day, how many times do you swing back and forth between loving the stuff you’re working on and hating it? Two times? Ten times? Fifty times? I’ve never kept track, but I know there can be a lot of love/hate for me, even within an hour.

But that’s the nature of the work. And it’s why we love the solopreneur life — it’s never dull and it’s seldom predictable.

With that, let’s look at 21 things we love and hate about being solopreneurs.

1. You LOVE Not Having This Guy As Your Boss


2. You HATE Your Inner Taskmaster


3. You LOVE Coming Up With Brilliant Ideas


4. You HATE When Your Ideas Don’t Work

marketing sucks

5. You LOVE Getting Paid


6. You HATE When an Account Goes Past 60 Days

soprano nobody talk

7. You LOVE Being Productive

carrey productive

8. You HATE When Your Computer Crashes


9. You LOVE Whipping the Competition


10. You HATE Anxiety Attacks

spongebob scared

11. You LOVE Feeling Appreciated For Who You Are


12. You HATE When Nobody’s RT’ing Your Tweets


13. You LOVE Landing a New Client


14. You HATE When Your Biggest Client Dumps You


15. You LOVE Being Your Own Boss


16. You HATE When Your Website Breaks

computer died

17. You LOVE Your Staff

dog paper

18. You HATE Being Bone Tired and Working Against a Deadline


19. You LOVE When Criticism Rolls Off Your Back


20. You HATE When Your Kids Have a Day Off From School


21. You LOVE It When a Plan Comes Together


Solopreneurs, No More Dreamy Entrees Until You Eat Your Vegetables!

At the beginning of the startup stage, I’m in favor of dreaming big. But I think we as solopreneurs are being fed too many empty-calorie “just follow your dream and everything will be awesome!” entrees.

So to counter all of our high-fat dreaming, this post is a heaping helping of reality.

How Much Money Are You Risking?

From a financial perspective, what’s at stake when you launch a solo business? It’s a critical question, and the more we know about our risk and reward, the better our startup planning and decision-making will be.

Let’s look at some numbers.

● Assume you left a decent-paying job (let’s say $60k per year) in order to start your business.

● Assume your new business doesn’t generate a salary for you in the first two years.

● Assume that, over a two-year period, you invest a good chunk of your savings ($25,000) to finance your business.

● Assume you pull the plug on your business after two extremely difficult years.

Add it up. You lost $145,000. (And this assumes you are able to get a good job immediately after closing your business!)

Now look at the other side of the equation.

● Assume you are able to tweak your business at the very beginning of the process — prior to branding, naming, the business plan, or anything else.

● Assume you are able to make adjustments that turn a loser business into a winner — one that nets you $45,000 in Year 1 and 75,000 in Year 2.

In the scenario above, the decision to stop and smell the reality, to find and correct the flaws in your business idea, resulted in $265,000.

Where I come from, $265k is a lot of money and My Dream better be pretty darn good if I’m going to risk that much scratch. How about you?

The X’s and O’s of a Solopreneur Marketing Strategy

Strategy without tactics is the slowest route to victory. Tactics without strategy is the noise before defeat.
—Sun Tzu, military strategist and author of “The Art of War”

We are so close to our businesses and its everyday details that we have difficulty answering the bigger-picture questions. We can break through that blockage by analyzing an entity that we are fond of, an entity that we observe from a distance.

In an article at his Web site, John Jantsch described the differences between a company’s mission, objectives, goals, strategies, and tactics.

A marketing strategy is a clear explanation of how you’re going to get there, John said. An effective marketing strategy is a concise explanation of your stated plan of execution to reach your objectives.

To become the market leader is an objective, he said. To serve our customers with honor and dignity is a mission. To double the number of new customers is a goal.

To wrap my head around these concepts, I placed them in a sports context, specifically the near-term prospects of my NFL team, the Cleveland Browns, commonly referred to as the “Hapless Cleveland Browns.” (I’m nothing if not loyal.) So with the clarity of the football example helping me, I applied John’s definitions to my business. The results are below.

Give this process a try, and put an interest of yours in place of the Browns. For example, it could be a favorite musical group, local organization, or company.


Mission in John’s example: serve our customers with honor and dignity
Mission for the Cleveland Browns: put a product on the field that Clevelanders can be proud of
Mission for The Solopreneur Life: help solopreneurs reach their business objectives and goals


Objective in John’s example: become the market leader
Objective for the Cleveland Browns: contend for Super Bowl titles
Objective for me: be a leader in providing resources, connection, and community to solopreneurs


Goal in John’s example: double the number of new customers
Goal for the Cleveland Browns: win 8 games in 2011, 10 games in 2012, average 10 wins per year from 2013 to 2018
Goal for The Solopreneur Life: hit revenue of x thousand in 2011, x thousand in 2012, with x percent gains from 2013 to 2018.


Strategy in John’s example: a clear explanation of how you’re going to get there
Strategy for the Cleveland Browns: in the 2011 Rookie Draft, select: a big-play receiver, a right tackle who someday could be an all-Pro, a cornerback who can start immediately and eventually become an all-Pro. In the 2012 Rookie Draft, select an impact player in the front seven on defense, and a quarterback. For current players, retain the services, long term, of Joe Thomas, Alex Mack, Joe Haden, and T.J. Ward; make a decision at the end of the 2011 season regarding the viability of Colt McCoy as the quarterback.
Strategy for me: develop and execute marketing plans for three areas: local business, online advertising revenue, and product sales. Develop and execute a content plan for all properties.


Tactics in John’s example: not given
Tactics for the Cleveland Browns:
• Attend the all-star games and the NFL Combine and focus in particular on the positions of need
• Identify 50 players at each position and analyze every play from their past two seasons
• Identify 10 finalists at each position, interview them, their coaches, find out everything we can about them
• Rank from 1 to 10 the top 10 players at each position
• Rank those 30 players
• At the Rookie Draft, select our highest-ranking player when it’s our turn to pick

Tactics for The Solopreneur Life:
• Frame all decisions within an attitude of service and giving
• Be intentional about obtaining client feedback
• Use surveys and social-media for gauging client needs
• Test local newspaper, school publications, postcards, cold calls, other methods; adjust, based on results
• Create a media kit for prospects, identify prospects who would benefit; ask prospects to advertise
• Establish a product calendar for 2011 and 2012, backed by marketing plans;
• Establish weekly content goals for, Facebook, Twitter, BlogTalkRadio
• Measure performance of tactics and cut those with a low ROI

I could go on and on with a list of tactics, but I hope you get the idea!

Share Results With Your Fellow Solopreneurs

What did you choose to analyze? What insights did it reveal about your own business? Please share your comments below.

Solopreneurs, Use This Method to Make Every Decision a Great Decision

What’s the most valuable skill a solopreneur can possess?

Marketing brilliance? Maybe.

A gift for sales? Every small business needs it!

Financial prowess? Very helpful.

Production efficiency? An absolute necessity for a solo business.

A Spartan work ethic? You can’t be a solopreneur without one.
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