How Freelancers Actually Grow - A Coach’s Inside Look at What Works (and What Doesn’t)

Every freelancer wants to grow, and one way to grow faster is to hire a business coach. That’s when the trouble begins.

Even under the best of circumstances, only 10% of coaches can be the best at what they do. Your results will vary based on which coach you hire, what specific results you’re after, and how committed you are to the process.

“It was a waste of time and money,” a designer told me. “The coach made everything about mindset.”

“It was totally worth it,” a marketer said. “Most of my biggest breakthroughs came after I hired a coach.”

The question is, how can you be confident you’ve found a great coach before you pay anything?

For starters, read this post. You’ll learn what good coaching is not, the approach that works the best, and why good chemistry matters.

You’ll also learn the simple fix—not easy, but simple—that changes everything: letting the business roadmap anchor one-on-one coaching sessions.

By the end, you’ll be more confident in your ability to find and hire the right business coach for you. Be sure to grab the 10 self-coaching questions at the end.

What This Post Covers

• What Good Coaching Is Not
• The Best Approach to One-on-One Business Coaching
• Chemistry matters, so schedule a free call.
• Ask about a strategic roadmap tailored for your situation.
• Look for a well-defined coaching process.
• The Single Most Valuable Thing Coaches Offer
• Don’t forget to download these 10 self-coaching questions.

What Good Coaching Is Not

Imagine that you’re a rock climber attempting El Capitan, and in the middle of a gnarly pitch, your legs start shaking and your arms start burning. From above your climbing coach yells, “Don’t let fear make your decisions! Act from a place of abundance!”

Various freelancers I’ve spoken with have had an experience like that with business coaching. They feel like they’re holding on for dear life, and they were looking for clear instructions: “Do this. Okay, good. Next, do this. No, not that way. This way.”

Instead, they get some vague, hand-wavy advice, often about the freelancer’s “mindset problems,” leaving them frustrated and no closer to the desired outcome.

Do freelancers have our fair share of fears, thought defects, and limiting beliefs?

Of course we do.

But when you’ve reached the crux and you’re tired and uncertain, you want a path forward, not a pep talk.

At least, that’s how I define good coaching: the timely delivery of practical, step-by-step guidance for overcoming obstacles.

A good coach already sees the breakthroughs because the coach has been there, done that. That better perspective enables the coach to explain the right order of moves to get out of a tough situation and into an exciting opportunity.

The order matters because it helps freelancers avoid rework. For example, before my own coaching clients create and launch a new offer, they use my playbooks to tune up their differentiators and positioning and more clearly define their target audience.

Why?

Later, when it comes time to dress up the new offer in really sharp, persuasive messaging, they’ve already arrived at the right words, phrases, metaphors, stories, and ideas. Et voilà!

One last observation before we move on: You don’t change your mindset by thinking about your mindset. You change your mindset by changing what you’re committed to.

A good coach helps you pinpoint what to do next and commit to a bigger vision for your business and life, which usually involves discomfort.

The Best Approach to One-on-One Business Coaching

I’ve coached dozens of advanced freelancers since 2018, and the most effective approach to one-on-one coaching I’ve found combines holistic, big-picture concerns with the type of real, actionable advice that I just mentioned.

Think of this as the both-and approach.

Given that many successful freelancers reach out to me when they’re tired (or already burned out), I can’t, in good conscience, encourage them to sacrifice their physical and mental health in pursuit of more profit.

We must think through self-care, your business strategy, and its long-term sustainability.

Meanwhile, we must suss out which projects represent their “best money” and implement client-getting tactics to increase revenue.

Freelancers have bills to pay and mouths to feed, and I’ve learned that coaching clients measure the success of our engagement by how many measurable breakthroughs they had, not by how supportive I was. Effective coaches bring more growth than tissues.

Chemistry matters, so schedule a free call.

Speaking of growth, business coaching isn’t like high school sports where a person with a clipboard and a whistle barks orders at you.

You get to decide who coaches you, and psychological safety is important. It is the harness on the roller coaster. If you can’t be vulnerable and excruciatingly honest with your coach, then you can’t move and grow as quickly.

You’re also looking for good chemistry.

Your coach doesn’t need to become your new best friend, but you should share things in common beyond an interest in business: faith or values, season of life (e.g., you both have kids), sense of humor, area of specialization, wiring (e.g., ADHD), or complementary skill sets.

I’m sensitive and empathetic. I’m 99% sure I have ADHD, though I’ve never received a formal diagnosis. I’m a Christian, and my values, especially humility, kindness, and gentleness, shape how I treat other people. I have three kids. I love to laugh, and yet I tend to be very direct.

Many of my clients have different faith or none at all, but multiple aspects of who I am match who they are. They want access to what I know, but they also appreciate how I make them feel.

Am I the right coach for every freelancer?

Absolutely not.

Any number of things about me might get on your nerves: I can be verbose. On occasion, I give advice too quickly; I should have asked follow-up questions. I prefer to walk during coaching sessions. I give homework assignments.

It’s important that you look forward to the one-on-one sessions with your coach, and the best way to answer that question (”Do I want to spend time with this person?”) is to schedule a complimentary strategy session.

Even a virtual coffee where you spend fifteen to twenty minutes getting to know one another can teach you a lot. Trust your gut.

To schedule a complimentary session with me, answer these questions. I'll follow up with you.‍



Ask about a strategic roadmap tailored for your situation.

Business coaches are different. Shocking realization, I know.

Some are highly organized. They follow a well-defined process. They rarely improvise.

Other coaches improvise most of the time.

Here’s my hot take: Improvisation leads to unhappy freelancers.

If I always let my coaching clients pick the focus of every session, then most default to whatever is top of mind.

The problem is that whatever is top of mind usually is not what is most strategic.

Life and business always throw us curveballs, but if I’m going to help my coaching clients accomplish, with my advice and playbooks, what they were unable to accomplish on their own, then we need to spend most of our time on implementing their custom business roadmap. (More on that in a moment.)

Good business coaches create a strategy and plan tailored to your specific situation, and then they hold you to it.

Look for a well-defined coaching process.

As I mentioned, effective coaches follow a well-defined process while knowing that they’ll have to adapt it to each client’s goals, needs, and life circumstances.

To give you a clear idea of a business coaching process, I’ll describe mine.

I don’t claim that it’s the best in the world and deserves seven honorary doctorates and a house in the highlands of Scotland.

I can say that this process has helped dozens of freelancers redesign their businesses, hit their income goals, and enjoy the rest of their lives more.

I’ll share each distinct step and, when appropriate, I’ll provide concrete examples from past coaching engagements. And I’ll do my best to keep things light and illuminating before we get to the freebie at the end (my 10 self-coaching questions).

• Step 0 - Sales
• Step 1 - Onboarding
• Step 2 - Roadmapping
• Step 3 - Commitment
• Step 4 - Sprints
• Step 5 - Support

Step 0 - Sales

I’m a firm believer that the right coaching clients for me are smart, brave, and motivated enough to invest in their futures without aggressive, high-pressure sales tactics.

For that reason, my discovery calls with potential clients and my overall sales process are laidback and straightforward:

• They spend 85% of our time together describing their challenges. I listen, ask follow-up questions, and take lots of notes.
• At the end, I explain what my coaching engagements look like, and then I shoot over an email after the call with a recap and next steps.

Example: A Freelance Writer Named Amy

A freelance writer named Amy gave me permission to write a case study about her experience, and I’ll pull from it to illustrate how a typical coaching engagement unfolds.

Amy had subscribed to my weekly newsletter and gotten a lot out of the Party Time blog posts. She eventually reached out to me to ask about coaching, book a complimentary strategy session, and discuss what she wanted to accomplish:

1. Create a strategy offer. She had tried organizing her ideas multiple times but had never actually put a strategy offer in front of a real prospect.
2. Cut her hours in half. She’d been grinding through a dense calendar for months and wanted to work less without earning less.
3. Raise her prices. She hadn’t touched them in three years.

Amy also told me that she wanted to see a qualitative change in her life:

• She was suffering from serious burnout.
• She wanted slower starts to her mornings.
• She wanted time to draw, learn French, and visit Paris.

Based on Amy’s goals, I was confident that Amy would move past her previous roadblocks if she took my advice and used my playbooks. I knew I could draw on personal, firsthand experience when coaching her:

• I’ve been self-employed as a freelancer for 16 years and counting.
• My business has gone through multiple iterations and evolutions. I’ve lost count of the number of clients served (well over a hundred).
• I’ve pivoted to selling strategy.
• I’ve burned out and recovered from it.

After the initial strategy session, I sent Amy a recap of our conversation, explained how I work with freelancers like her, and told her what to expect, price wise. (You can find my current pricing on the freelance business coaching page.)

Amy wanted to move forward, so she followed the next steps I sent her:

1. Read and signed the short, no-surprises coaching agreement.
2. Paid the $2,500 deposit that covers the custom business roadmap and Month 1 of coaching.*
3. Answered the onboarding questions. More on that below.

Sidenote: The deposit comes with a 100% money-back guarantee.

Step 1 - Onboarding

Before we do anything else, I send my new coaching clients twenty to thirty onboarding questions.

No two freelancers are in the exact same situation, and better questions turn up better insights.

I have designed questions that bring clarity at two levels:

1. Higher level that the client already has some awareness of. Each client has goals, desires, obstacles, ideas, opportunities, and points of leverage.
2. Lower level that the client is less aware of. Each client has a “substrate” of assumptions, fears, hesitations, contradictions, lies, limiting beliefs, mental traps, emotions, and ambiguity.

This substrate drives much of our decision-making and behavior, and I help clients go down to that level and unpack some of the boxes in the metaphorical basement.

We identify the dream that got stuffed down, taped shut, and relegated to the One Day shelf.

Will the freelancer achieve that dream in just six months?

Usually not, but it is incredible to watch what happens after we bring the dream upstairs, so to speak, put it on display, and admit, “This is what I want.”

The bold act of defining the stakes unlocks fresh passion, imagination, and energy. The client lights up with optimism and joy. New pathways open up.

Before the impossible can become possible, we have to speak it. Change starts with honesty.

During the first roadmapping session, I also look for three specific things that will determine what goes in to the client’s roadmap: the client’s true north, quick wins, and contradictions.

Example: Amy’s Pricing & VA Situation

A good example of a quick win was Amy’s prices, which she hadn't touched since 2022. We both knew that raising them would enable her to recoup most or all of her investment in coaching.

The onboarding questions also turned up a contradiction when Amy told me three things about herself that ordinarily don’t go together:

• “I have two VAs.”
• “I’m working too much.”
• “I don’t have good systems.”

“Hold up,” I said. “VAs are supposed to take things off your plate so that you don’t work too much. They can be responsible for creating systems and processes. Something here doesn’t add up. We need to peel back these layers.”

Some gentle probing into Amy’s thought process revealed the core problem and opportunity.

The problem was that Amy felt loyal to her two part-time, specialist VAs. Her loyalty was a good, admirable thing, yet neither VA was freeing up significant time and attention for Amy, which was not a good thing.

Once Amy acknowledged her two competing values, loyalty and time freedom, she was able to make a firm decision and act quickly. She parted ways with both specialized VAs and hired a single full-time, generalist VA. Getting more of the right support and delegating more repetitive admin tasks enabled Amy to spend more time working on her business and work less overall.

Her momentum and optimism picked up.

"So I looked at my effective hourly rate for the six months that we worked together, and it increased by 28%!"

Step 2 - Roadmapping

Between the first roadmapping session and the second, I start pulling together a draft of the custom business roadmap.

The roadmap is an actionable plan that helps the client in three ways:

1. Outcome. It clarifies what success looks like for the coaching engagement: “Here’s what we’re doing together.”
2. Pathway. The roadmap contains three to eight key projects or milestones required to achieve that outcome. I put them in the most logical sequence to avoid rework.
3. Focus. The roadmap eliminates ambiguity so it’s always clear what the client should do next, and what she should strategically ignore.

Many freelancers feel stuck, not because they’re unintelligent or unwilling to put in the work but because they have competing values like Amy or competing priorities.

They’re not sure which priority comes first, and as a result, they drift over into research, overthinking, and second-guessing.

A roadmap keeps you unstuck and brings the future into the present by clarifying what you must do next, day to day, week to week, to get what you want. It helps you use your selective attention to notice what aligns with your goals and forget about the rest for the time being.

Example: Amy’s Roadmap

Amy’s roadmap included these projects and milestones:

• Set direction.
• Rethinking my prices.
• Nail down my ICP.
• Update positioning and messaging.
• Productize my signature offer.
• Nail down my strategy offers.
• Establish a Morning Marketing Habit.
• Delegate more–joyfully.

Because she worked on her prices and ICP (i.e., ideal customer profile) first, she later found it easier to knock out her positioning, messaging, and offers.

She successfully launched her strategy offer and started putting it in front of prospects in her chosen market (InsurTech).

And because she knew what she wanted to sell and to whom, it was easier to pick marketing strategies and tactics and define systems and processes with her VA.

Quote from Amy about her strategy offer:

"Launching the strategy offer is, like, the biggest win. [...] It's ridiculous how long I have been thinking about doing that."

Step 3 - Commitment

Between Session One and Session Two, I bring the roadmap to 98% completion by adding specific steps under each milestone to make it abundantly clear what the client needs to do.

When those steps require a training, playbook, or worksheet, I add the links. When they require thinking or reflection, I provide the prompts.

Once I’m satisfied, I share the roadmap with the client.

We then meet one-on-one again to color in some of the final details:

• Subtraction List. What belongs on your Don’t Do list? What should you subtract to make more room for what is most important?
• Mental Traps. What are your mental traps and hiding places? What might prevent you from using this roadmap and getting 10x out of your investment in this coaching engagement?
• Anti-Goals. Do we need to define any qualifiers, constraints, or “Anti-Goals” (what you want to avoid while you pursue your goals)? (h/t Jay Clouse)

Eventually, we reach the point where adding more to the roadmap would make it too complex and overwhelming and, therefore, less effective as a tool.

Knowing that, I’ve gone so far as to gray out later phases or parts of a roadmap and tell the client that simplicity scales:

“That part is here, preserved, ready for you. But thinking about it right now is detrimental. Give yourself permission to forget about it for now and focus on the very next step. You’ll advance faster that way. Simplicity scales.”

With clarifications and explanations out of the way, we reach the end of the second session when I ask the client two commitment questions:

1. Do you believe in this roadmap?
2. Do you commit to this roadmap?

If she answers yes to both questions, then we pick her first assignment, or two-week sprint of effort.

That vocal action turns the roadmap from a tool into a commitment. It’s simple but powerful: “I said I was going to do this. Now, I have to do this.”

If she answers no, I refund all of her money and give her the roadmap. I don’t want to work with clients who don’t believe in their own plan. (For the record, I’ve never had a client be unready to commit. They’re always eager to get to work at this point.)

Step 4 - Sprints

Now, the real work begins.

The client and I meet every two weeks for forty-five minutes.

The purpose of those sessions is to track progress against the roadmap, workshop the client’s assignments, and keep the momentum going.

At the end of each session, we decide what will go into the next two-week sprint.

It’s worth adding that the workload will never be too heavy or punishing.

Every client still needs to spend the bulk of their time running the business. They can’t afford to pause everything while they redesign and rebuild it.

Though I do use the sprint language, which I borrowed from software engineering and agile development, my clients need a sustainable, satisfying cadence. They need rest and recovery along the way. I’m sensitive to that reality, and may even tell my hard-driving, go-getter clients to slow down, not speed up.

We increase or decrease the pace, as needed, to respond to everything that’s happening in their businesses and lives.

Example: Key Outcome of Amy’s Sprints

Six months after we started working together, Amy and her business are in a different place:

• She raised her prices and gave herself a 28% raise without logging a single extra hour.
• She turned a sporadic client into an anchor account that sends her three or four articles a month and plenty of lead time.
• She finally shipped her new strategy offer.
• She told me that her confidence grew, that she takes her business more seriously, and that she feels more comfortable taking risks.”

Step 5 - Asynchronous Support

Earlier, I mentioned that most coaching clients would default to using our one-on-one sessions to talking about whatever was top-of-mind, usually a curveball. I also mentioned that sticking to the roadmap is the better use of our time.

That’s true, and I still help my clients navigate those needs and situations by providing asynchronous support through email and DMs.

Here are several real scenarios that come to mind:

• Renegotiating the compensation package with a founder you don’t fully trust
• Dealing with pushback from a client unaccustomed to paying for strategy
• Working through mental blocks while creating a bigger offer
• Parting ways with a self-centered, volatile CEO
• Rehoming a loyal but underpaying client
• Subcontracting other freelancers

Whether it’s a quick reality check (”You’re not going to change the CEO’s personality”), morale boost (”Look at how far you’ve already come!”), or recommendation (”Here’s how to think about paying subcontractors… .”), my role as a coach between sessions is to help clients stay unstuck.

I may critique their new messaging. I may point out a blind spot. I may refer them to the right web designer, hiring platform, or app.

I send a lot of video messages because that’s usually faster and more helpful than writing a long email.

Freelancing can be lonely, and more than anything, I provide the reassurance and support that matter even more than the tactics.

Clients will also share their wins with me, day to day, week to week. It’s nice to have someone to celebrate with, right?

Check out this video from another coaching client named Josh. One of his wins was going on more non-working vacations with his family.

The Single Most Valuable Thing Coaches Offer

As we close, I want to be very clear about the single most valuable thing that coaches offer.

It’s not the crunchy outcomes like Amy charging 28% more, Josh going on a cruise with his family, or the $30,000 in new strategy business that Rachel sold.

Believe it or not, the most valuable thing I do is ask my freelance coaching clients to pay me.

Financial commitment forces mental commitment. When we pay, we pay attention. We show up at our level of investment.

Investment creates a point-of-no-return situation that helps us to break out of avoidance patterns.

Fear, hesitation, and self-doubt keep us stuck, but once we spend the money, whether it be on an expensive coach or community, personal trainer or program, we know we can’t afford to come up empty handed.

For example, my gym costs $10 per month. My personal trainer Melissa charged me $240 per month. She was twenty-four times more expensive, but you already know which option got me in better shape.

Why?

The financial “shock” of the investment sends a message to our subconscious: “I have to advance now. I must engage.”

Free and inexpensive information isn’t effective for the opposite reason. There is no shock. The cost of inaction is next to zero.

How many life-changing books go unread because they cost only $9?

Whether you work with me or a different coach, the principle is the same: Leverage your own psychology by paying for progress.

Use a painful financial commitment to create a point of no return situation for yourself. Cement your mental commitment, narrow your focus, and spur your growth.

So if you want progress, pay for it.

If you want to explore working with me, fill out this form. I’ll follow up with you.

Whether you’re a freelance copywriter, designer, or consultant, coaching for freelancers isn’t about giving you a generic plan — it’s about helping you make better decisions, faster.

Don’t forget to download these 10 self-coaching questions.