12 Important Things I’ve Learned in 20 Years as a Soloist

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On June 16, 1997, I declared myself “open for business” as a soloist and a brand strategy consultant.  I did this from the desk in my spare bedroom.  I don’t recall thinking, “I’ll be doing some version of this 20 years from now,” but here we are.

I’m very happy with how things have turned out, and I’m proud to have reached this milestone.  Below are 12 things I’ve learned along the way.  I hope they may be of benefit to those of you who are considering working for yourself, or are new to the game.

1. Keep a small nut.

Before you go out on your own, I recommend that you set aside at least 6 months of living expenses.  (And 12 months or more if you can.)  Why?  Because this is freedom: Freedom to pass on those sketchy gigs that come along, to ride out the inevitable valleys, or to tell that abusive client exactly where to go.

And remain fiscally conservative – the less you spend on overhead, the more freedom you’ll maintain.  You may not need office space, let alone a goddamn foosball table.

2. Treat it like your job, not a side gig.

Every time the job market tightens, “freelancers” are suddenly thick on the grounds.  Some of them will even tell you: “I’m only doing this until I find my next job.”  Not the most confidence-inspiring take.

Few people last 20 years in this game, but I think one reason I have is that I was never a short-timer.  Consulting is my business; it’s what I wanted to do.  So I’ve been able to take the long-term view in all major decisions.  It matters.

3. Go narrow, not wide.

In other words, define exactly what you’re best at, and exactly who cares about that.  Define exactly the work you’d most like to do.  Define exactly who you want to serve.

This can feel counterintuitive.  You may be inclined to cast a wide net, especially when you’re concerned about putting food on the table.  But if you’re clear about what you do, you’ll do a better job of attracting the business you want – and others will have a mental “box” in which to place you.

I was bad at this when I started out.  At first, I called myself a “marketing consultant,” which tells you very little.  Once I decided I would specialize in positioning and strategy for challenger brands, my business took off.

The added benefit of making a clear choice is that you tend to become an expert.  If you go deep in a focused area, you’ll get pretty good at it.

4. But keep an open mind.

Some projects will come along that will stretch you in new ways.  This pays dividends well beyond the project fee.  For instance, partnering with Interbrand gave me invaluable exposure to the world-class design strategy thinking of both Interbrand and P&G.  Working with Eureka! Ranch, the leading innovation think tank, made me fluent in both facilitation and ideation.  Embrace those opportunities that will add a new wrinkle to your brain.

5. Your time is your inventory.

Productive use of time is one of the hallmarks of the successful soloist.  Every minute matters.   At the least, you need to efficiently manage your calendar and priorities.  Find the system that works for you, and keep it as simple as possible.

You’ll have to invest some administrative time to keep the business running.  Minimize this time, automate it, find the right software or job it out.

6. Live a full life.

When you’re a soloist, there can be a sense that you should be working all the time.  Every hour you invest should translate to income, right?  Wrong.  You’ll come to be worn-out and one-dimensional.  I encourage you to shut the machine down often.

I’m happier when I exercise daily, eat well, sleep eight hours a night, and pursue outside interests.  As a result, my work time is sharper and more productive.

7. Schedule your vacations.

Breaking my own rule and checking email in Napa, May 2017.

I’m embarrassed to admit that I went many years before I took a full week away from the business.  And that only happened because I scheduled the vacation months in advance.  Now, I do so regularly.

As a soloist, it can be scary to completely step away. But with a bit of planning and the miracles of modern technology, it’s easier to do than ever.  And it’s necessary.  So do it.

8. Work hard and work smart.

You may have had a manager who advised you to “Work smarter, not harder.”  This is a false choice.  You should always find more intelligent ways of delivering quality work, but that doesn’t mean you can be lazy.  If you work hard and work smart, you’ll be almost certain to succeed.

9. Follow the “Beer Rule.”

If you wouldn’t get a beer with the people across the table, don’t take them on as clients.  Most people are, at the least, pretty decent.  But some aren’t.  And every time I’ve ignored my gut and violated this rule, I’ve regretted it.

10. Maintain “beginner’s mind.”

As a soloist, you’re often paid to be “the guy with the answers.”  After a few years of this, you might come to believe that you actually have all the answers.  That’s precisely the moment you become stupid.

Keep learning, both within and outside your field.  And read as much as possible.  Many great thinkers have done us the favor of putting their thoughts on paper.  Take advantage of this inexpensive schooling.

11. Do meaningful work in a healthy environment.

Over the years, I’ve learned that my work has to meet two criteria: It has to have meaning, and it has to happen in an environment that’s positive and respectful.  If either of those components are missing, I’m anywhere from uninvested to miserable.

I’ve been very lucky in the client department, but I’ve also had clients who were condescending and unprofessional.  I’ve had clients who expected free work.  Some clients expected me to hit my deadlines, which is quite reasonable, but were also rather slow to pay invoices, which is not.  These are symptomatic of an unhealthy environment.

And some businesses want to collect eyeballs and profits, but without doing a damn thing to make the world a better place.  That’s not work that matters.

There are plenty of companies who are doing the right things and doing them right.  There’s really no point in partnering with anyone else.

12. I’m not a soloist.

Despite what the headline says, I couldn’t do this alone.  The support of family and friends has often smoothed a rocky path for me.

I won the lottery in the parental department.  Twenty years ago, when I told my parents I was considering life without a paycheck, there was no second-guessing.  I remember Mom’s words vividly: “If anyone can make a go of this, you can.”  During the bumpy times, it’s been good to have her words to call on.

Historically, I was less lucky in the romance department.  I didn’t really know what it was like to have a significant other who was truly supportive of (and curious about) my work until recently.  A little more than a year ago, I made that person my wife.  Kara, thank you for your support, your perspective, and everything you do to make every day better.

The number of people I could thank for this 20-year run is way too long to list here.  But I’m grateful for every one of the clients, collaborators and sounding boards who made it possible.  And when I pop that celebratory bottle tonight – probably the 2006 Robert Sinskey SLD Cabernet Sauvignon – it will be to you that I toast first.

About Matthew Fenton: Matthew helps challenger brands to focus, grow and win.  Since founding his consultancy, Three Deuce Branding, in 1997, he’s helped hundreds of brands to achieve “brand clarity.”  His consulting services and speaking engagements help brands to focus on what matters through positioning, strategy and ideation.  Contact Matthew here.  He calls Chicago home.

Copyright 2017 – Matthew Fenton. All Rights Reserved. You may reprint this article with the original, unedited text intact, including the About Matthew Fenton section.

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