The 3 Freelance Fundamentals That Keep Saving My Business

This is a post about three freelance fundamentals that can’t steer you wrong. Before I get into them, let me tell a quick story about what prompted this post.

In June 2025 my business partner and I bought an first investment property. It was a first for me, and the fulfillment of a part of my Vivid Vision I first committed to paper in December 2022. As a newbie, I faced a steep learning curve. I was confident I could figure it out. I did figure out it.

However, putting all that time and attention into launching the short-term rentals and coworking space came with a cost. Revenue in my other business cratered in June. July wasn’t much better.

That wasn’t the first time I’ve had several down months in a row as a freelancer, and this time around, I was proud of myself for making a a rather cool assessment of the situation. Not enough inputs (marketing and business development) had predictably produced not enough outputs (conversations and opportunities). Of course my pipeline has the merest trickle running through it! Of course my income had gone down!

To expect something other than the mathematical relationship between marketing inputs and sales outputs would have been wishful thinking.

As my wife and I burned through our savings and then some, I had a choice to make: catastrophize by imagining the worst that can happen and then sprinkling rusty nails and asbestos on top of that or returning to the fundamentals.

I chose the latter.

Fundamentals are principles bound up in practices that can’t steer you wrong.

Though fundamentals don’t have a cause-and-effect relationships with the outcomes we want, they come pretty darn close. High correlation, let’s call it instead.

Two examples will illustrate:

• Think about the effect of eating more leafy vegetables on your health. Assuming you’re not allergic to any of them, you can’t go wrong with more nutrients and fiber.
• Think about touching base with past clients every 90 days. Whether you point them to a resource, share an idea, or simply say hi and ask about their kid or most recent trip, you can’t go wrong. You’re bound to intercept more projects because you stayed top of mind.

Fundamentals work and keep working, and aside from that reliability and effectiveness, they have value because they often don’t require as much brainpower as novel ideas or innovative solutions. They won’t seem particularly clever or original because they’re not. That’s a good thing, especially when you’re yanking on your mindset like the reins on a misbehaving horse. Even when you’re feeling wound tight, nervous, and breakable, you can stick to the fundamentals. You can keep building your business on what won’t change.

When I’m in a revenue dip, as I was this past summer, I doubled down on these three fundamentals—again.

Fundamental #1 - Start new conversations

By start new conversations, I mean take the most direct path available to starting conversations with the people who have money and can make the hiring decision.

To start new conversations, you don’t have to be “good at marketing” or to “enjoy sales.” I purposefully didn’t use the words “marketing” or “sales” because those words stir up tornadoes of insecurity for freelancers.

You don’t even have to agonize over your reluctance to “put yourself out there,” wherever in the Milky Way “there” is. You do have to connect with individuals.

Some of those people will represent net-new relationships. A marketing director writes a LinkedIn post about how fast the company is growing. You send her a DM and offer to pitch in and help. The worst that she can do is tell you to scram, an unkindness which you will survive.

Other conversations you start will be with people you already know. Friends who got new jobs. Former coworkers, colleagues, or collaborators you haven’t spoken to in a while. Past clients. Other freelancers who aren’t direct competitors. Some who are direct competitors, but why not? The pie is big enough.

Conversations, not elaborate strategies or clever tactics, is always the goal. Even advanced freelancers have a tendency to lose the plot as they explore the marketing circus with its many rigged games and sideshows. We can generate all sorts of marketing-adjacent motion and yet be no closer to real conversations with real decision-makers about real needs they have.

I’ll sometimes ask my one-on-one coaching clients, “Is there a more direct path to getting what you want?”

Most shift uncomfortably in their chairs and admit that there is. “I guess I could just email her.” Or hand-write a letter. Or send a DM with a voice message. Or record the Loom video. Or put together an intriguing lumpy mail package. Or pick up the phone. Or stop by their office. Or have fun doing your own ingenious test project, posting about it, and mentioning the dream client it’s for.

All too often, we let how we feel in the moment tell a story about our well-being and future business prospects. You may feel sick about your income or debt. I know that feeling, friend. You may be walking with a metaphorical limp after another disappointing month and thinking, what if things never get better? You may have a lingering mood that your kind of annoying poet friend would describe as “purple tinged with glass shards.”

Take heart. Our moods only become dark prophecies and the depressing stories we tell ourselves only come true if we do nothing. Fall back on this fundamental. Start conversations, and you’ll get leads.

(If you haven’t already, check out this post on being an opportunity hound.)

Fundamental #2 - Keep promises.

Do whatever you said you were going to do.

When we don’t have enough clients, enough work, or enough revenue, we may spend more time trying to get your mind right. More time preparing to work than actually working.

As a result, it’s easy to procrastinate on the projects and work you do have. This neglect usually is more a by-product of that misbehaving mindset than a conscious act, it does compounds the problem. How will you get repeat business, introductions, and referrals from existing clients if you don’t knock their projects out of the park? How will you knock their projects out of the park if moping and a malaise of bitter distractedness make you sloppy with details, due dates, and communication?

When I find myself tempted to put on the mental sweatpants and prolong a slow season or temporary cash crunch, I say these two things to myself:

• Put your hand to the plow.
• Love the client right in front of you.

Sometimes, I also connect with my inner Anna from Frozen 2 and whisper, “Do the next right thing.” Cheesy as it sounds, it helps me prevent disappointment and flabby thinking from turning into a lack of discipline or even disaster. It helps me avoid piling self-sabotage on top of the original problem.

These words remind me of my agency and power: I can act in ways in the present that align with the future I want. I want to be known as a husband, father, friend, son, coach, and consultant who keeps his promises. I want to stay in integrity with my clients and myself by keeping your promises.

These questions help me make a plan of attack:

1. Did I tell somebody I would do something today or this week? What commitments to others did I make?
2. Did I tell myself I would do something? What commitments to myself did I make?
3. What project deadlines do I have?

When you don’t feel like it, keep your promises. When you’re scared, keep your promises. No matter what, keep your promises.

Fundamental #3 - Improve.

People joke about “rearranging deck chairs on the Titanic,” and there is such a thing as wasteful improvement.

What I’m talking about here is finding one issue in your business each day to fix or improve.

For example, after my partner and I bought the investment property, I hired a new bookkeeper. Faced with the prospect of keeping the books for the LLC, I opted to delegate. The bookkeeper won’t cost the company very much. She’ll do the work better and faster than I would. She’ll enable me to focus on getting the property to profitability sooner. She is an improvement over me.

Improvement as a business fundamental may seem laughably obvious, but it’s not. Some creatives and consultants keep getting the same mediocre results year after year. More experience doesn’t automatically translate into better results for them. They don’t improve because they don’t use the free but necessary ingredient that converts the crude oil of experience into the gasoline of fuel: reflection.

If you aren’t getting the results you want, you must do three things:

• Carve out time to reflect on your recent experience.
• Keep asking why about the issue until you drill down to an actionable insight.
• Fix the issue that day, if possible, or identify the very first step and take it.

I didn’t hire the bookkeeper in one day, but I did write the job description and post it on Onlinejobs.ph. The definitive step precipitated the chain reaction.

What’s wrong with your business? What can you do about that today? What’s in your control?

Separate what you can control from what you can, and use the 5-minute unlock to solve problems and improve faster.

Ask this question so you don’t hide.

Before we close this post, I must point out the improvement trap. Many freelancers, consultants, and agency founders love to stomp out small, solvable problems that are, in fact, distractions.

For example, even if you don’t have nearly enough work coming in, you’ll want to use ChatGPT to write a the code snippet for the new email signature like the one you saw from the freelancers who’s cooler than you. Your old signature was a source of irritation, a regular paper cut against your brand, and the creating the new one delivered a dopamine hit.

Small, solvable problems are a trap because they give us a place to hide from bigger, harder-to-solve problems. The “don’t like my email signature” problem shouldn’t take priority over the “not enough revenue” problem. It won’t change your circumstances. It is pseudo-progress.

To avoid hiding in such second-order problems, ask yourself this question from the book, The ONE Thing: “What’s the one thing, such that by doing it everything else becomes easier or unnecessary?”

That question brings us to the most fundamental of all fundamentals: Throw everything you’ve got at the problem, even when you’re not fizzing with optimism, and you’ll change your position for the better.

Speaking of changing your position for the better, some advanced freelancers and consultants need to make a financial commitment to cement their mental commitment. Investment creates a point-of-no-return situation that enables my coaching clients to break through the avoidance patterns that were keeping them stuck. When they pay, they pay attention. They show up at our level of investment. That’s precisely why free resources, including this post, have limited effectiveness. If you know you need to make a can’t-go-back commitment, read this page about my one-on-one coaching engagements. It covers how they work. Also, read this recent case study about Amy, too.

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. Freelance Cake Community. Build the business you really want with people who really get it.
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.