5 Predictable Ways Freelancers Fail

Warren Buffett’s late business partner, the inimitable Charlie Munger, attributed Berkshire Hathaway’s success in part to being “a little less stupid than most people.” That core principle has become gospel among Buffett and Munger acolytes: “Avoid standard ways of failing.”

What are those standard ways for freelancers and consultants?

I’m going to share 5 of them after we have a bit of fun.

A One-Act Play: “Generalists Who Insist on Staying Generalists Until”

Now that I’ve been a one-on-one business coach for 7 years and counting, I’ve heard dozens of freelancers and consultants insist that dead-end strategies and tactics will work for them.

They really believe what they’re saying, but even if their goals and situations are unique, their problems aren’t.

Same ol’ problems, and same ol’ solutions.

As a conscientious coach, however, I can act like an insensitive dad and bark orders because dad knows best. No, I must facilitate a process of self discovery for clients through the Socratic method, lay out the logic, and let their intelligence and good judgment take the lead.

Even so, here’s a one-act play I’d pay good Bitcoin to never sit through again:

Freelancer: “I like being a generalist. I can help clients across industries, and I like the variety. I’m worried I’d get bored if I were to specialize.”

Me: “Okay, sure, the spice of life. I understand the appeal. How’s that working for you?”

[Sometimes, I’ve got to embrace my inner Dr. Phil.]

Freelancer: “What do you mean?”

Me: “You say you like being a generalist. You worry you’d get bored. Are you charging exciting, premium prices for interesting projects and doing work you’re really proud of for great clients?”

[several moments of pregnant silence]

Freelancer: “Not as often as I’d like, no.”

Me: “Is it reasonable to think you can keep doing the same things and get dramatically different results?”

[more silence]

Freelancer: “Probably not.”

Me: “Every freelancer and consultant I work with is good at more than one thing. I am. You are. We’re all generalists. So the decision to specialize is more about narrowing the scope of your marketing and lead generation and positioning yourself as an expert for a specific group of people. Clients prefer to hire experts, and they’ll pay a premium to work with a recognized authority. It’s less risky for them.”

Freelancer: “Okay, I guess that makes sense.”

Me: “And besides, I’d pick a boring, reliable, profitable business over one that is unpredictable and constantly triggers anxiety about money. I can find excitement and creative fulfillment in other areas of my life.”

Freelancer: “What happens when I get a lead or a referral outside of my specialization?”

Me: “Say yes. Be an opportunist and cherry-pick the best projects that find their way to you, but be very specialized and focused in your public-facing marketing and messaging.”

Freelancer: “I never really thought of it that way.”

Me: “For what it’s worth, I don’t think you’ll find people reaching out to you already sold on working with you and agreeing to whatever price you put in front of them to be boring. You’re more likely to experience relief.”

[curtain closes]

Standard Way of Failing #1: Staying a Generalist

There’s so much talent and noise out there these days. Clients always have a cheaper option.

It’s fine to be a generalist if your business is hyper-local and you’ve got more business than you can handle through referrals.

However, 90% of freelancers reach a point where their existing networks aren’t producing a steady enough supply of good project leads.

Dependence on referrals represents a single point of failure in their businesses. Their businesses are fragile.

And if they’ve slapped together enough revenue by being a one-stop shop for marketing, design, writing, whathaveyou, then they’ve got a math problem yoked to a positioning problem:

I’m not a recognized authority who solves a painful, expensive problem for a specific group of people, and I’m not getting enough leads which forces me to take whatever I can get.

I’ve seen it 217 times, or thereabouts.

How can you avoid this standard way of failing?

Many of us, myself included, start as generalists because we aren’t sure yet what we want to focus on or what pays the best. Fine.

Sidle up to the buffet and sample everything. Then, niche down. Quickly. Don’t stay a generalist. Your second plate should be piled heaping high with niche.

How do you know you’ve found a good niche? Because it involves a starving crowd, which is the one advantage freelancers need most.

Specialize in whom you serve and what problem you solve for them and how you solve it.

Combine that who-what-how with proven results, and the how much becomes inconsequential for ROI-minded clients.

Listen to this podcast episode where I share 16 benefits of niching down.

Let’s quickly look at 4 more standard ways of failing.

Standard Way of Failing #2: Undercharging

Pricing is hard on its own for creatives and consultants, and money is a thorny subject for most of us.

The mere mention of money is enough to make freelancers start sweating and looking for exits.

For reasons I fully unpack in my pricing and money mindset guide, Free Money, we don’t raise our prices often or high enough.

Freelancing is hard enough, and undercharging compounds problems.

You have to work more to hit your revenue target, which leaves less time for marketing and lead generation.

Lower prices attract price-conscious clients who are more demanding, disorganized, and difficult.

They tend to refer people like themselves, and thus you create a vicious cycle.

How can you avoid this standard way of failing?

Proactively raise your prices when you’re not ready to raise your prices.

If you don’t have a straightforward step-by-step process for that, buy my book. If you don’t finish books, buy my Smart Strategic, Pricing Bundle instead.

Best $17 you’ll spend this year.

Standard Way of Failing #3: Weak Positioning

Positioning assumes that you’re positioned against someone or something else in the market. A hot dog stand is not a kebab stand.

A lice treatment center does not offer sports physicals. (Don’t ask me how I know this.)

As I mentioned, freelancing is hard, but you can make it easier on yourself by picking a horizontal specialization (whom you serve) and a vertical specialization (what you do for them).

Draw a circle around that uppercase T, and you’ve got your how: how you do it.

For example, my friend Paul owns a managed IT services firm and they only work with Microsoft’s suite of products.

Do they “lose” clients who want to use MacBooks or Google Workspace. Sure. But they’ve doubled down on what they can do well, and they’re doing just fine.

It’s not enough to be a specialist. You must have positioning statements and other messaging that demonstrate your deep knowledge of your clients’ unique situations. When they read your web pages or LinkedIn About section, they need to feel like you’re reading their minds.

How can you avoid this standard way of failing?

Brainstorm your key differentiators, then narrow that list to the 5-8 that are most important or valuable to your dream clients.

Then, think about specific ways that your personality, character, background, work experience, specialized knowledge, and soft skills enhances the how in your who-what-how.

Then, think about your dream clients’ problems, pain points, common mistakes, limiting beliefs, objections, and stupid industry norms.

Then, mix all that into a strong, fragrant positioning stew. Cooking metaphors for the win.

If you prefer to follow a step-by-step process so you don’t overthink it, apply to join the Freelance Cake Community for advanced freelancers.

You’ll get free access to my Positioning and Messaging playbooks.

Standard Way of Failing #4: Generic Services

On a Wednesday in January 2025, my wife had to take herself and our three kids to a clinic. She knew they had lice and suspected she might. Sure enough, two hours and $834.29 later, all four of them walked out with heads shellacked with goop (official term) and the peace of mind that can only come from a full heat treatment.

Why didn’t we buy a box of goop from Walmart or Amazon? Because lice are disgusting parasitic insects that live in our hair and because we didn’t have full faith that the off-the-shelf option would solve the problem of crawly, sesame seed-sized yuckness. A business can’t get more specialized in the problem it solves and for whom than “Knoxville Lice Clinic.” We coughed up the cash and solved the problem quickly.

Without going into the nitpicky details (pun intended) as to why, I found that most freelancers haven’t zeroed in on a small, discrete set of painful, expensive problems they solve. Instead, they keep descriptions of their services broad like “Conversion Copywriter” or “Copywriter for B2B Companies.”

That’s a mistake.

Generic services are forgettable, and freelancers who offer them are forgettable, too.

I’m not knocking you if you’re in that boat right now because most freelancers are. I’m pointing out the opportunity.

How can you avoid this standard way of failing?

Pick a dream client. You do have to pick.

Figure out what their main problems are related to the work you do. Then, use the noggin God gave you to rank the problems from most painful and expensive to least.

Once you’ve got the frontrunner, think about the client’s current frustrated state: What are they thinking? Doing? Feeling? Now, dream a little on the client’s behalf: What would business and life look like if that problem vanished? What would they be thinking? Doing? Feeling?

Great. Build a juicy offer around that desired future state, especially the functional benefits (what they’ll get by working with you) and emotional end benefits (how they’ll feel as a result).

Unlike generic services, juicy offers are tied to the client’s desired outcome, or desired future state. And “client” here isn’t someone who can pay you but a specific decision-maker in a specific industry or market vertical.

You’ve heard the riches are in the niches, and it’s true. Just ask the lice clinic that took all my money and left me feeling full of gratitude.

Standard Way of Failing #5: Inconsistent Lead Generation

“I don’t like self promotion. I’m not good at putting myself out there. It’s easier for me to rep other people’s stuff than my own.”

My coaching clients say things like this all the time. Their reservations about getting or even wanting attention are as predictable as my kids asking for dessert after dinner.

Marketing, business dev, lead gen—it doesn’t come naturally to most freelancers and consultants. Many of us feel conflicted about it. The people who most want attention online and the people who show up most often in the news are the ones least deserving of our attention, let alone our respect.

So we come to the false conclusion that self promotion or getting attention is tacky or unsavory. It’s beneath us.

You’ve now entered the tough love segment of today’s programming.

My friend, being good isn’t good enough. The most talented freelancers aren’t the ones making the most or attracting the best clients.

We cannot keep our heads down, do good work in our private, calm caves of brilliance, and have clients come to our doorstep and throw chic suitcases full of money at us. The English language has a phrase for that approach to business development: wishful thinking.

It doesn’t work.

How can you avoid this standard way of failing?

Make yourself the easiest, obvious choice for your dream clients by showing up consistently online.

Develop a Morning Marketing Habit so that you’ve put in your daily marketing effort while your willpower is at its peak.

The best marketers win, not the best freelancers. An always be marketing practice is the way you generate a surplus of project leads, and that surplus makes other business problems simply disappear. Have a difficult client? Replace them with a better one. Working too many hours? Hire a VA and bring in a subcontractor to handle admin and parts of projects you don’t enjoy.

If you’re not getting leads consistently, shed the wishful thinking. Change what you do. Change.

Okay, phew, Business Dad Moment over.

Start now.

One last standard way of failing is to procrastinate. Surely, you’ve thought of something you need to change.

Are you gonna?

Perhaps these two questions will help you organize your thoughts:

1. What are the standard ways freelancers and consultants fail?
2. How do the best freelancers and consultants avoid them?

To avoid standard ways of failing, make a list of what they are. Make a list of their opposites. Build your plan around the opposites.

When you’re ready, here are ways I can help you:

1. Free Money. A pricing and money mindset guide for freelance creatives. If you’re unsure about your freelance pricing, this is the book for you.
2. Morning Marketing Habit. This course will help you build an “always be marketing” practice, become less dependent on referrals, and proactively build the business you want with the clients you want. My own morning marketing habit has enabled me to consistently make  6 figures as a freelancer.
3. 1:1 Coaching. Gain clarity, confidence, and momentum in your freelance or consulting business.
4. Business Redesign (Group Coaching). Raise your effective hourly rate, delegate with confidence, and free up 40 hours a month.
5. Clarity Session. It’s hard to read the label when you’re inside the bottle. I've done well over 100 of these 1:1 sessions with founders, solopreneurs, and freelancers who wanted guidance, a second opinion, or help creating a plan.