Blog • Resources

Freelance Interview Series – Long-term Success with Matthew Fenton

Matthew Fenton is a brand strategy pro, owner of Three Deuce Branding, and the creator of Winning Solo, a freelancer coaching business that helps other solopreneurs design balanced lifestyles. A freelancer for 25 years and counting – he’s an expert at building habits and processes tailored to individuals who work for themselves (you can sign up for his newsletter to get soloist strategies in your inbox on the reg).

We asked him to share some of his insight into making the entrepreneurial lifestyle manageable and fulfilling long-term.

1. Was it always your intention to turn freelancing into a long-term career?

I’d like to say that when I began consulting in 1997, I knew I’d still be doing it in 2022.

But that would be a lie.

One thing I did know for sure, though, was that certain aspects of traditional employment didn’t agree with me. And I saw self-employment as a way to do more of the stuff I enjoyed, and less of the stuff that I didn’t.

I was always conscious of the idea that freelancing could be a key component in a happier, more balanced life.

So I never treated freelancing as a fallback or a stopgap. It was my intention to stay in the game as long as possible, and I made my decisions accordingly, and here we are 25 years later.

2. Have the services that you offer shifted over time?

They have. Today, my consultancy, Three Deuce Branding, only deals in what I call “core brand strategy”: aspirations, positioning, strategy, and messaging. So I’ve chosen to go “narrow and deep.” I enjoy solving the puzzle and creating the top-level brand strategy.

I don’t do any execution at all, though quite often I partner with creatives, create one-off teams, or help my clients manage their execution partners.

In my early days of freelancing, I told people I was a “marketing consultant,” which is about the same as telling them nothing at all. So I attracted a lot of inquiries that were outside my expertise, like building websites and designing logos. I refused those, but I was foolish enough to accept a few copywriting gigs until I realized that I (a) didn’t enjoy it and (b) wasn’t good at it.

The lessons: A precise offer is better than a vague one. And — shocker! — expertise matters.

In March of last year, I launched Winning Solo to help other freelancers enjoy greater earnings, longevity, and balance. Right now, it’s a coaching business, though I plan to launch courses soon. Because this is a different market and offering than my brand strategy consultancy, it made sense to me to brand Winning Solo as its own thing.

3. Do you have set goals for your business (long term and short term)? If so, how often do you revisit your holistic business strategy and set new goals for yourself?

LOVE this question. I’m regularly stunned — stunned, I tell you! — by the number of freelancers who tell me they do no planning at all for their businesses.

The very short answer: I set annual income goals and I revisit my strategic plan every quarter. I block a full day to do this, though it almost never takes that long.

Some tips I’d offer to freelancers who struggle with (or simply dread) planning:

Go with the “Minimum Viable Plan.” You don’t need some clunky, formal, 30-page binder. You’re not pitching to investors. Go with the most lightweight approach that helps you get the job done. My own plan fits on a single page.

Plan your quarter, not your year. A year is difficult to conceptualize and easy to procrastinate within. Thinking in terms of 90-day windows helps you to prioritize and execute.

Establish a weekly “top two.” To further help me prioritize, I allow myself a maximum of two business-building priorities per week. These are my “As”; everything else is a “B” or lower. These usually fall out of my 90-day plan, but I have a quick check-in with myself every Friday to establish my “top two” for the coming week.

Focus on inputs, not outputs. Just wanting to earn $200k won’t make it happen. Think in terms of the behaviors that are most likely to result in achieving your goal. Most often, these take the form of projects (e.g. a deep-dive on mastering sales) or habits (e.g. publishing and contributing on social media every day).

There are no mandatory tactics. The core strategic question is this: What are the best choices to get me to where I want to be? Since we each have different starting points, strengths, objectives, and obstacles, it follows that our choices will be different.

So you can ignore that guy in the Facebook ad who tells you that you MUST build a funnel, or be a content machine, or whatever. The right tactics are the ones that work for you.

4. Throughout your journey, have you sought out any coaching or mentorship?

I’ve done less of this than I should have. This is partly a function of starting out in the ‘90s when there weren’t that many experienced freelancers to learn from. And it’s partly my own psychological wiring — the “lone wolf” thing.

So I executed a dive of my own selection and learned from the mistakes as I went along. This is an expensive way to go about it, though. It’s much cheaper to learn from the experience of others.

5. What do you think are the most important skills to work on and grow as a career freelancer (outside of the services offered)?

The first one would be: “Get very good at the work, and get very good at the work that brings you the work.”

We’d like to believe that excellent work is enough to win the day, but that’s not always the case. I’ve seen some very talented freelancers crash out because they couldn’t or wouldn’t embrace marketing and sales. Treat yourself like a client and prioritize your own business.

It need not be sleazy or complicated. You can think of marketing as “consistently bringing value to people who can hire you.” You can think of sales as “listening to understand.”

The second skill: effective use of time. As freelancers, our time is our inventory, so we need to invest it well. Regularly ask: What am I doing that can be minimized, automated, outsourced, or ignored?

Even the must-do stuff can often be done more efficiently or effectively. If part of your job requires that you’re on social media, but it feels like you’re spending too much time scrolling, the first step is to put a number to that so you can reduce it.

6. What advice would you give freelancers who want to turn their service offering into a long-term career?

Four quick bits:

The primary reason for your business to exist is to meet your needs. It’s not the only reason, but it is the primary reason. If your clients are delighted but you’re miserable, what’s the point? If in doubt: Life plan first, business plan second.

Everyone is not your client. You can’t serve “the universe.” Sharpen your targeting, qualify your prospects, and know your terms of engagement. The difference between great clients and lousy clients can be the difference between many years of freelancing and an early exit.

Do exceptional work when given the chance. That’s how you build a reputation. And that leads to referrals, repeat business, and clients who take you with them when they change jobs.

Protect the asset. (You are the asset.) I stole that line from Gregory McKeown; I think every freelancer should read his book Essentialism. You can’t do your best work if you’re burnt out or off balance. Make time for exercise, sleep, family and friends, hobbies and interests, reflection, and gratitude.


Give Matthew a follow on Twitter or check out Winning Solo to learn more about how to grow your business in a sustainable way.

About the AuthorSamantha is co-founder of Harlow. Previously she was a marketing and demand gen freelancer. She enjoys traveling, connecting with new people, spending time with her dog Karl, and throwing back an extra dirty martini every now and then.

Never miss the latest and greatest freelancer resources. Join our email list.

You may also like:

Share This