But for most Freelancers, the internet’s real power lies in its ability to connect.

Exploring the “structural seduction”

You start a Freelance business and have zero clients. So you look up “how to get freelance clients” and find a polished 40-minute video from someone with 200K subscribers.

They tell you all about their totally revolutionary Freelance Client System, which consists of:

→ a lead magnet
→ a 7-email nurture sequence
→ a sales call to close

So you spend two weeks building a lead magnet nobody asked for, writing automated emails to people who don’t exist yet, and creating a landing page for an audience you don’t have. And after all your hard work, you hesitantly push “Publish.”

No one downloads it.

It’s a distraction

The internet whispers: build a system. Create leverage. Work smarter, not harder.

Because the person teaching you isn’t making their money by getting clients for freelancers. They’re making money by teaching freelancers how to get clients.

That’s a completely different business.

They’re in the business of ranking #1 for “how to get freelance clients” on YouTube – a game that rewards whoever can produce the most polished content, optimize for the algorithm, and build the biggest audience.

From there, they can generate thousands of leads, convert a small percentage into a $997 evergreen course, and make far more money than they ever could actually doing freelance client work.

So you’re left with this weird dynamic where the loudest voices are all saying “scale, automate, systematize” – because that’s what worked for them.

But most of us aren’t playing that game. You don’t need 10,000 leads; you need five great clients.

What works for me

I’ve tried both approaches.

I’ve done the cold outreach blasts. The automated email sequences. The “scale-first” mentality.

And I can tell you: ~100% of my best projects and clients have come from my network and referrals.

The internet’s real power isn’t that it lets you automate outreach to strangers. It’s that it lets you build actual relationships with people you never would’ve met otherwise.

Here’s how I think about doing that…

Reaching out to people who inspire me.

says: “One of the easiest ways to build a 10x network is to reach out randomly to people who inspire you and tell them so.”

I listen to a ton of podcasts, and always make sure to connect with or follow anyone I listen to and find interesting. Then maybe tell ‘em a bit about why.

Engaging with content I genuinely enjoy.

I’m aiming to be more thoughtful in engaging with the things that actually move me – especially on places like Substack, where I think there may be a lot of like-minded folks wandering these digital halls.

Real comments, not “great post!” bulldinky.

Treating content as a magnet.

In the past, I’ve thought of content more like a “system” to get new clients: If I just posted enough and said the right combination of words, revenue would magically appear.

I think that approach can work.

But I like thinking of content more as a way to filter like-minded people online. When someone resonates with something I write, that’s a signal we might click. It’s the start of a relationship.

Then, connecting with people who engage.

Since I treat engagement as a signal, I like to look deeper into nearly everyone who engages with my stuff.

If someone leaves a thoughtful comment or likes a bunch of my posts, I’ll check out their work. Maybe follow them. Maybe reach out.

(This only works if you’re genuinely approaching content as a way to filter like-minded people.)

Having more conversations and calls.

I’m trying to turn more online relationships into actual calls, where I can really see if I vibe with someone.

No real strategy – I simply pay attention to how I feel during and after a conversation - do I feel energized or depleted? If energized, keep building that relationship.

And if it really clicks, ask: “Who else should I meet?”

A different vision

Considering scale might make sense if you’re building something truly transformative that needs to reach millions of people.

But if you’re running a professional services business? The focus on scale and automation is a distraction.

Worse, it’s dehumanizing. When you’re optimizing for thousands of leads, people become conversion rates, and relationships become “touchpoints.”

Maybe we can choose a different way.

We can use the internet to really connect with people. To build relationships that matter and serve clients you genuinely care about serving.

Scale when it makes sense. But start by building something extremely valuable for a small group of specific people.

KISS = Keep it simple, stupid.

Just ‘cus we’re building an online business, doesn’t mean that we have to build it in some ‘internet-specific’ way.

Seems to me that the internet’s potential scale has led many of us to make business a lot more complicated than it needs to be.

Especially because it unlocks these two capabilities:

1. It expands our potential market from the local area to anyone with a wifi connection.

2. It allows us to automate, and the purview of what we can automate has just grown significantly due to AI.

So I think it becomes tempting to focus on scale and automation before focusing on the timeless business principles that have worked since the first time someone bought a thing:

1️⃣ Do good work.
2️⃣ Make strong connections.
3️⃣ Be clear about what you do.

Get these right first.

Then layer on growth marketing tactics to reach more people and amplify what already works.

These are the 3 stupidly-simple business principles that need be the foundation of everything you build - and yes, they are in order of priority.

#1: Customer Experience

This is the foundation. Always has been, always will be.

A necessary ‘step 1’ for owning a business is to deliver an exceptional product or service to your client.

Can’t do that? You shouldn’t be in business.

The way I see it, there are two major aspects of customer experience:

👉 Doing good work

This means being good at our craft and deliberately sharpening the skills necessary to add more value to our clients’ lives.

I think an additional aspect of this – and this may be the harder part – is focus.

Many freelancers stall their own growth by spreading themselves too thin, so that the skills they gain from one project don’t really impact the next.

Narrowing your focus – on a specific type of client, project, or offer – will make your efforts compound.

Each project becomes training for the next.

👉 Doing it in a good way

Everything you do more than once should have some sort of system around it.

Nothing complex – I tend to think simple is better, actually. Basically everything I do lives in Google Docs (not exactly high-tech).

But it’s important to map out every part of the process so that you can make it as simple as possible for the client:

→ Be clear and prompt with what you need from them (and why)
→ Set clear expectations up front
→ Deliver work in a way that’s organized (templatize what you can)
→ Break the work into clear stages with visible progress

Vance Morris, the Godfather of Customer Experience, describes it as orchestrating the whole experience so the customer never feels uncertainty, friction, or “what’s happening next?”

It’s simple – just make it seem like you’ve been there before.

#2: Relationships

Alice Lemee, Freelance Writing Coach, wrote:

“I get asked a lot about where to find clients. The truth is that almost all of them come from referrals. This shouldn’t be discouraging! Rather, it should remind you to always invest in relationships.”

This completely correlates with my Freelancing experience, too.

I’ve done the cold outreach strategies…
I’ve done the automated email funnel approach…

But if I were to look back at my past projects and be honest with myself, something becomes very clear:

~100% of my best projects and clients have come from my relationships.

Simple as that - either people I’ve already known, met through networking, or projects I was referred. Those are overwhelmingly the best projects I’ve worked on in my freelance career.

Not to say other strategies are useless – the cold outreach tactics and UpWork job postings are necessary at some points in our Freelance work. We need to get paid, after all.

But my main focus needs to be on building relationships.

And while I love meeting new people of all sorts, we should really focus on meeting two types of people:

→ People who serve the same clients as you, in adjacent ways
→ The clients you actually want to work with

Define these so you can be deliberate with where you spend your time – both online and off. Simply being in the same proximity as this group will give you a massive advantage.

And it doesn’t have to feel like stuffy, ‘collecting business cards’ networking. It can mean…

→ having good conversations
→ being genuinely curious
→ allowing yourself to express more than just “my toned-down work self”

My goal is stupidly simple:
meet cool people.

One of the original promises in the early day of the internet was to connect like-minded people you never would’ve otherwise met in day-to-day life…

Somewhere along the way, that idea got buried under growth hacks and funnels.

You can build a successful online business by treating every online interaction as a “lead” – simply playing a numbers game – and not recognizing that there’s another human being on the other side of that screen.

Plenty of people have done this, and then packaged their system into an online course for just $999.

But I’d rather try to make genuine connections.

Not just because it’s “good for business”... but because it’s good, full stop.

SURPRISE... we’re actually wired this way.

We’ve evolved to need each other. Community shouldn’t be something you find outside of work hours. Or at least it doesn’t have to be.

#3: Clarity

They say “riches are in the niches.”

And while that may be true, I’ve found it better to arrive at clarity by doing the work, rather than trying to define it all upfront.

I first heard the concept of architect vs. archaeologist from David Perell, describing two completely different approaches to business/career:

🚧 An architect plans a building up front before construction begins, then diligently follows that plan.

A person with a clear goal and long-term plan.

💎 An archaeologist doesn’t have a clear vision of where they’re going – this person follows their interests, collects experiences, and slowly uncovers a deeper purpose along the way.

In hindsight, every single “misstep” – no matter how random at the time – was a critical part of the archaeologist’s path.

I think of myself as an archaeologist. Seems to me most Freelancers are.

I used to view this as a flaw. I’ve never been able to set a “5 year goal” that I actually stick to, but I think there’s actually something valuable about this attitude. As Shane Parrish explained on the Crazy Good Turns podcast:

So instead of defining an ‘ideal path’ and then following it step by step, it may be more beneficial to simply focus on the process:

Do great work. Meet great people.

And along the way, start to clarify who you are – your unique niche. David Whyte’s concept of the conversational nature of reality has helped me understand this process:

🫵 You want something.
🌍 The universe wants something from you.
🤝 And the conversation is what happens between the two.

And this is sort of what happens when finding your niche, too.

You want something…

→ The projects you enjoy most
→ The clients you’d love to work with
→ The media formats that interest you most

The market wants something…

→ Where does your work make the biggest impact?
→ Where is your work most needed?
→ Who’s willing to pay the most for your work?

Your niche lives at the intersection of these.

And once this intersection starts to appear, it’s important to name it. Because defining your niche as a Freelancer has ripple effects on every aspect of business:

💸 What you’re paid… as much as we may like the marketplace to be a complete meritocracy, it’s not. Your positioning will have a bigger impact on your revenue than skill.

👀 Who pays attention… the way you speak about yourself determines who you attract, and who you repel.

💬 How people talk about you… especially critical in a referral-driven business. People need a simple way to explain what you do.

This is where most Freelancers hesitate – understandably so.

Saying “this is my niche” can feel like closing doors. But when done right, choosing a lane for your business should open up way more opportunities than it shuts down.

So start by defining who your work is for – a very specific audience you serve. As Seth Godin says:

“Make difficult decisions about who it’s for, and then ignore everyone else.”

Once you’ve gotten clear about the who, everything else fall into place more easily:

What are you selling them? (start from: what problem do these people need solved?)

Where are you sharing it with them? (start from: where do these people spend time?)

Again… keep it simple, stupid.

There’s a version of business where you generate thousands of leads, expect most of them to ignore you, and hope the math works out in your favor.

And then there’s another version.

One where you focus on doing good work, building real relationships, and being clear about what you offer — and only then, thinking about expanding your reach.

Neither path is objectively right or wrong.

That’s the gift of freelancing.

You get to choose.

Which business do you want to run?

Must’ve been a Senior in high school at the time. And I was jealous.

Partially because of the drug-fueled lives and the borderline-unbelievable stories it led to. I thought that was ‘cool’ at that point in my life. Maybe I sorta still do?

But mostly – and I don’t think I recognized this at the time – I was jealous of the obsession these music icons had with their instrument and craft.

I was really having fun with the guitar, but it clearly isn’t the same for me as for the Jimi Hendrixes and Stevie Ray Vaughns of the world. I had about an hour and a half before my attention would drift, and I’d be ready to do something else.1

And this jealousy wasn’t about the guitar specifically.

Guitar was just a hobby I got into when a torn UCL ended my high school baseball career a bit early. I had time to fill.

But these biographies made it clear that I didn’t have this level of obsession for anything.

I loved baseball – it was a major part of my identity for years. But I also knew I didn’t have the same level of obsession as my peers who were surpassing me. While they were putting in the effort to get ahead, I was happy playing Xbox with my buds.

So I was jealous.

Kobe or Cubicle

“I was probably 10 years old,” Kobe tells CNBC.

“A guidance counselor asked me what I wanted to be when I grow up. I said I wanted to be an NBA player. He said ‘you know, that’s not very realistic. I think you should consider something else.”

Kobe explains to the journalist:

These are the stories of success we’re told. Our society loves the story of a prodigy with a freak-of-nature work ethic… the chosen one.

They always knew. They had a singular obsession from day one. They couldn’t not do the thing - even after facing rejection. A level of devotion that led to inevitable success in their field.

But the rest of us?

While we’re told to “follow our passion,” we quietly suspect we don’t have one of those capital-P Passions. Not like that.

We don’t wake up at 5 a.m. craving jump shots.
We don’t lose track of time, being so deep in practice that we forget to eat.
We don’t have that “I’d die without this” energy toward any one thing.

Meanwhile, the other examples we’re shown aren’t exactly inspiring.

It’s the people who dread work, drain their energy doing something they hate, and then spend nights and weekends trying to refill the tank to get through another day.

Those who say things like…

“Everybody hates their job,” and “Welcome to the real world, kid.”

And when those are the two models presented, the unsaid message begins to calcify:

Either you’re born with some obsessive, all-consuming passion… or you’re destined to work a job you tolerate at best and resent at worst.

The problem with passion

(a simple etymology breakdown from Professor GPT)

‘Passion’ comes from the Latin verb pati → “to suffer, endure.”

Originally, it referred to the Passion of Christ, referring to Jesus’ suffering during the crucifixion.

Then usage evolved.

In the Middle Ages, passions referred to strong emotions… the passions of the soul.

From a Christian lens, these passions weren’t celebrated. They were impulses to be tamed, distractions pulling us away from God.

During the Renaissance, usage shifted to what we recognize today. Passion became a way to describe inner desire or enthusiasm, especially in art or love.

Today, we also use it in performative ways:
“I’m passionate about data analytics,” says the candidate in a job interview.

Though we still understand when the use of ‘passion’ is phony, so clearly the word hasn’t completely lost its meaning. We know what true passion is.

And that idea of ‘being overtaken’ by passion still resonates.

Think about that Kobe story.

He clearly made a choice – “I want to be a basketball player.” But on some level, it feels like he didn’t (especially since he was so young).

Overtaken by passion, he was just along for the ride.

This all makes me wonder if the ‘follow your passion’ advice is a sort of cop out.

If passion is something that happens to you, then the absence of it isn’t your responsibility. You’re just waiting for fate to make the call.

It’s difficult to choose your path in life, especially in a world filled with “what ifs”.

So we tell ourselves that others didn’t choose – they were overtaken by passion… they always knew what they wanted to do. It’s an easier perspective to hold.

Otherwise, the responsibility would be on us to make the incredibly hard choice of:

What do I want to do?

So instead, when we’re not overtaken by a passion, we defer to an easier question:

What should I do?

This question has real, concrete answers and data from the world around us. Other people will gladly tell you what’s “smart” or “practical” or “what you need to do.”

We can look to the people ahead of us on the ladder and ask – “am I doing this right?”

But when we ask What do I want to do? there’s no one to answer but us.

A new problem

It’s easy to take for granted how far we’ve come.

For most of human history, career wasn’t a question: You did what your father did, what his father did before him, and the father before that.

Destiny.

Today, we’re handed the opposite set of circumstances. We have the freedom to choose how we spend our working lives – and the potential choices are literally endless.

Like Uncle Ben said:

“With great power comes great responsibility.” And I’ll make a slight edit to that:

With great freedom comes great responsibility.

And boy, does that responsibility bear weight. Especially in our secular, capitalist world, where a large chunk of our identity is tied to our occupation. This choice shapes how people see us and even how we see ourselves.

So we dodge that responsibility in a few ways:

1️⃣ We outsource the decision (what should I do?)

2️⃣ We minimize its importance (my job isn’t my life…)

3️⃣ We wait for passion to overtake us (then it’s not our fault if it doesn’t)

The good news

We have a potential path that prior generations didn’t have access to.

The term “lifestyle design” was coined in Tim Ferriss’ book The 4 Hour Workweek, and describes intentionally shaping your work to support the life you actually want to live.

It seems to me that this idea of a “lifestyle business” is seen as sort of silly or non-serious. But after my Father passed much too early last July, I have a very different perspective:

‘Cus he built his own business – he did Business Valuations.

It wasn’t something he had a capital-P passion for. He didn’t care about Business Valuations in the same way Kobe cared for basketball.

But essentially, he built a “lifestyle business” before that term even existed.

He didn’t build a business to scale it to the moon.
He didn’t build a business to chase status and external validation.

He built a business that allowed him to prioritize time with my sisters and me –

He drove us to school every day.
He was at every single one of our baseball and softball games.
He chauffeured us to our friends’ houses.

And since his passing, it’s become apparent how important all this quality time truly was.

The most important, really.

It was only possible because he prioritized spending time with us. And I’m not so sure that’s even possible when working for a company – we can say that our family is the priority, but our actions say the opposite when we miss family dinners and are glued to Slack on the weekends.

So what am I saying here?

I’m proposing a hopeful future. Where a person’s Life doesn’t have to come second to their Work.

I hope for a world with more Freelancers and Solopreneurs, where people work in ways that align with their unique preferences, tendencies, strengths, and perspectives.

Where the average person is presented with more choices than ‘Kobe or Cubicle.’

And it seems to be the way the tides are turning, anyway, which I’m excited about.

Not so people can work less or “slack off” (which is how Corporate Shills tend to frame it).

But so people can do work that highlights their strengths, motivates them, and supports the life they aspire to live.

To me, that feels like a future that’s better for all of us.

So I’ll leave with that hopeful thought.
Thanks for reading!

“Hard work” is considered a virtue.
“Sacrifice now to succeed later.”
“Nothing worthwhile comes without suffering.”

It made me visualize success as something that demands a ton of friction – forcing myself to sit at the laptop for another few hours by deadening the deep part of me that’s ants-ing to do anything else.

I’m not sure it needs to be this way.

Personally, I refuse to burn myself out like this. So I’m operating under the belief that if I operate like ⬇️ this ⬇️, I’ll actually be more effective than if I grind in a way that’s scattered.

• Consistently: Showing up to improve myself a tiny bit every single day… but not to the point where it becomes excruciating.

• Focused: Deliberately building skill and learning in specific areas that’ll directly help my clients and my work.

• Intentionally: Treating everything I do as a rep – not just something to finish, but as a path to improvement.

• Driven by Curiosity: Because it doesn’t have to be boring:

  • Find the aspects of your craft/industry that are interesting… hone in on those.

  • Find the thought leaders in your craft/industry that are entertaining… learn from them.

  • Find the real-life outcomes that truly drive you (i.e. family, impact, future freedom)… and connect your work to those.

Then just keep pushing the goal posts… 🥅

Some people operate well with long-term goals. Big, 10-year visions. I don’t, so I can’t really speak to that.

If I had to guess where I’d be today 5 years ago, I would’ve been completely wrong. And I love where I’m at right now, so I’m not sure I want to set a long-term plan for myself.

Instead, I think about simply showing up every day and moving the goalposts forward a little bit at a time.

It’s the approach Abraham Lincoln used (as explained by Cal Newport):

Lincoln was a voracious reader – but it doesn’t seem that he read randomly. He read to learn about very specific things that would make him more valuable.

“For Lincoln at first [it] was really self improvement. Then as he got solidified, he began to redefine useful to mean useful to other people:

At first, his town. Then useful to his county and then as he moved up in the legislature, useful to the whole state of Illinois. And then he moved to the national scale.”

And I use this perspective to think about growth in my own freelance business:

1️⃣ Start by developing skills for yourself.

This stage is about building capability in your core craft.

It’s getting good enough to simply be valuable, so you can make some money and pay your bills.

For me, it’s learning to be a good enough copywriter to feed myself and pay rent. Learning to deliver enough value to clients that it’d be worth paying me.

2️⃣ Then developing skills for the people around you.

Start learning how your craft fits into the bigger picture for your clients.

For me, it’s focusing on the larger growth outcomes my clients really care about… not just the copy.

This is where you go beyond deliverables and focus on outcomes. Start by helping your existing clients in a more strategic way – asking better questions, thinking holistically, and spotting opportunities.

(Some clients will want this. Others just want deliverables. No judgment, just know who’s who.)

3️⃣ Then develop skills to expand your impact.

This stage is about selling specific outcomes, not just your hours.

For me, it’s about taking what I’ve learned from past projects – what works, what makes the biggest impact, what clients care about – and packaging that into a clear, outcome-based offer.

Instead of selling a copywriting service, I help clients clarify their Differentiation Strategy and create messaging that reflects that.

It’s not about selling time anymore. It’s about selling results.

And to do that, you need to deliberately learn and develop a deep understanding in how your work fits into your client’s larger business machine.

4️⃣ And so on and so forth.

Deliberate vs. unconscious practice

“I fear not the man who has practiced 10,000 kicks once, but the man who has practiced one kick 10,000 times.”
Bruce Lee

There are two types of practice:

1️⃣ Deliberate practice: Purposefully choosing a particular skill, isolating it, and working on it with full awareness.

This is the type of practice that most of your competitors are not doing. So even a small amount of deliberate practice will put you miles ahead of the pack.

2️⃣ Unconscious practice: The passive improvement that happens over time simply by living, working, and accumulating experience day after day.

Like James Clear argues in Atomic Habits, every tiny action we take is a vote for the person we are becoming.

Deliberate Practice

One example of deliberate practice from my own craft (I’m a copywriter) is copyworking.

It’s a practice I discovered from Eddie Shleyner. And when I was early in my career, this deliberate may have been one of the most critical aspects of my improvement.

I’d sit down a couple nights a week and literally hand-write or retype great copy from the best in the industry. Line by line. Word for word.

It’s slow and borderline tedious… and definitely not productive in the way people obsess over (it ain’t getting me paid). But it trained my brain to absorb rhythm, structure, argumentation, and flow in a way that I believe was instrumental in my development.

Hunter S. Thompson used to do this, manually transcribing Hemingway and Fitzgerald to internalize the feel of great writing. And that’s the essence of deliberate practice:

Choosing a very specific skill you want to get better at, isolating it, and doing focused reps.

Small inputs in this area lead to big returns. And almost none of your competitors are willing to do this part.

Unconscious Practice

This practice is the one we don’t think about as “practice” at all.

As a human being, we are always getting better at something. Every action you take is reinforcing certain skills, habits, and patterns.

That’s unconscious practice: the constant, passive accumulation of reps by simply doing the work.

And as a freelancer, the projects you choose determine what you end up unconsciously practicing.

If you’re intentional about it, every project becomes:

• a rep toward the kind of work you want to be known for

• a rep toward the skill you want to sharpen

• a rep toward the positioning you want to grow into

• a real-world piece of your future portfolio

But this only happens if you approach your projects with this mindset.

If you don’t, it’s easy to slip into “just completing deliverables,” and you lose the chance to let the work compound.

Every project is practice, and so you must ask…

In what way can I use this project as a way to fuel my growth?

The goal of any practice is to develop Unconscious Competence in your craft.

That’s the stage when the fundamentals become automatic. When the things you once needed to consciously force now happen without friction.

For me, it’s been with copywriting:

When I first started writing direct-response copy, I was painfully aware of every persuasion principle I was trying to “use.” Thinking things like…

→ okay, here is the part of the copy where I need to really agitate the problem…
→ now I need to add the “aha” moment…
→ cue the testimonials so people actually believe me…

It felt formulaic because it was.

But after enough reps (both deliberate and unconscious), you stop forcing tactics and start writing with intuition.

The templates and principles don’t disappear. But they’re no longer top-of-mind… they’re simply a part of the way you think and execute tasks.

Developing your taste for “good” 🔍

It’s an intangible skill, which is why I think it gets overlooked. But I think that in the AI age, your taste will be increasingly important.

In a world where it’s becoming easier and easier to create…
what will matter more is your ability to sense what’s worth making.

Taste is the difference between publishing for the sake of it and publishing content that actually resonates with someone on an emotional level.

So, I think it’s important to refine your internal compass for what “good” actually looks and feels like in your craft.

How do you do it?

→ Consuming a lot of great content (inside and outside of your craft)
→ Tune into your genuine emotional reactions (this is a practice – the more we do it, the easier it becomes to tune in)
→ Collect the work that resonates

Start a swipe file for your favorite pieces within your craft. I’ve recently become a lot more intentional about this myself.

Rick Rubin, the legendary and notoriously non-technical music producer, explains the purpose of deliberately developing your taste:

“The objective is not to mimic greatness, but to calibrate our internal meter for greatness. So we can better make the thousands of choices that might ultimately lead to our own great work.”

To thrive as a freelancer in a crowded marketplace – to be seen as a true expert instead of just a contractor (and that’s the only way for us to grow as freelancers) – you need to build an expert-level standard of excellence.

So all this to say…

I don’t believe that thriving as a freelancer requires grinding your face off.

Simply caring about your work is the most reliable insurance that you’ll make it as a freelancer.

I’ll leave this with a piece from Paul Millerd’s blog post – Become More Serious:

I think it’s worth trying to become more serious about your life.

The most serious people I know are the most playful, the most alive, and the most inspiring.

But we think of being serious as a bad thing. “You’re too serious.”

No.

To be serious is to give a damn at a time when most people have stopped giving a damn.

Doesn’t need to be extremely hard. Just give a shit.

The stuff you can’t prepare for. The emotional rollercoaster no one brags about on LinkedIn. This piece is about that.

Here’s a list of the things they don’t tell you about freelancing. You’ll either learn now or through your own experience:

1️⃣ Prepare for a lot of uneasy feelings.

Doubt, feelings of not-good-enough, a low-grade hum of anxiety… these feelings of discomfort are both inevitable, and positive signs:

That you’re stretching into something bigger than you’ve done before.

That you’re on a completely new, untrodden path – your path.

That you’re building something that’s true to you, without a roadmap.

2️⃣ There is no “right” way.

Some people may try to tell you that they have the one, true way to success – and they’ll sell it to you in their course for 4 payments of $395.

And maybe their path to success works, but it isn’t the only one. There is no single path to building a successful freelancing business – and that’s what makes this journey both so rewarding and anxiety-producing.

So don’t go looking for THE “right” way, it doesn’t exist.

Instead, look for the right way FOR YOU.

3️⃣ It’s unpredictable by nature.

If uncertainty makes you uneasy, welcome to freelancing. You should expect that…

There will be major income swings.

There will be clients who ghost you.

There will be times that all the work in the world comes in at once.

The longer you’ve built your freelancing business, the easier it is to mitigate or prevent this unpredictability. But it should be an expected, inevitable part of the journey.

4️⃣ You’ll never be good enough.

Every new level brings a new round of doubt. That nagging voice that says you should be further ahead by now? It never shuts up completely.

Don’t wait until you feel like “expert” enough. The edge is in action, not preparation.

5️⃣ It’s not a failure. It’s a data point.

That offer that didn’t land, the client you lost, the pitch that bombed… these aren’t failures, they’re simply experiments.

The feedback is what helps you iterate toward a version of your business that both fits you best and ushers your most unique gifts to the world.

6️⃣ It’s not going to happen overnight

And you’ll probably doubt you made the right move.

It’ll probably take a decent chunk of time to scale back up to your prior income, especially if you were in your career for more than a few years before moving to freelance.

You’ll likely feel a strong urge to try to make things happen overnight, but that’ll probably lead to shoddy work. So my recommendation is…

Do good work in a brisk, but NOT rushed way. Growth (any change, really) feels slower in the moment than we’d prefer, when we’re in the moment – so zooming out when reflecting on your business is important, to recognize how far you’ve truly come and how much you’ve grown.

7️⃣ That expectation in your head? Not happening…

That mental picture of how freelancing “should” go? Throw it out.

Any sort of daydreamed idea of how freelancing will go for you is based on someone else’s experience. But freelancing forces such a unique path, you simply will not be able to replicate anyone else’s – and so, it won’t be anything you ever could expect.

Your actual path will be messier, stranger, and probably better for you than what you had in mind.

This post isn’t meant to condemn freelancing in any way. It’s simply to set expectations.

The other side of freelancing – the doubt, unpredictability, “oh shit, what have I done?” spiral – seems like a turn off. But this side actually contains many of life’s most profound lessons.

Maybe this struggle is simply proof you’re growing into the type of person who can handle the freedom, responsibility, and weirdness of this path.

• The time freedom.

• The location freedom.

• The opportunities for higher income.

But freelancing has a much greater impact than these surface-level tangibles. It changes our relationship to “work.” And ourselves.

#1: It puts you in the driver’s seat

Freelancing puts all the decisions back in your hands (not the company’s):

→ how will you spend your time?
→ what goals are really worth striving for?
→ which activities actually move the needle?

As an employee, your day is shaped by someone else’s agenda. Freelancing flips that.

When you’re no longer working through a to-do list that’s been assigned to you, you’re forced to decide what matters for yourself.

And how you choose to spend your time is a signal:

This is what I care about. This is where I’m headed.

#2: You learn more deeply about yourself

Freelancing forces you to set your own goals, which means asking: what do I really want?

Surprisingly, that answer doesn’t come that easily for most of us (me).

You’re no longer working off someone else’s expectations or company objectives – you have to know yourself well enough to create your own. That means paying close attention:

• What energizes me vs. drains me?

• What do I actually care about vs. just pretend to?

• What am I really trying to build here?

That’s why I think freelancing can be a sneaky spiritual path. It doesn’t have to be – but if you let it, it forces you to confront who you are, what you want, and what kind of daily life you’d love to build for yourself.

#3: It adds intrinsic motivation

When working for a company, I’ve only felt truly motivated for so long before it feels like I’m lying to myself.

Freelancing changes that: income is directly tied to your effort. And that need to pay the bills is motivating in itself.

But it also taps into something deeper: the urge to create.

Psychiatrist Paul Conti calls this our generative drive – the desire to create and contribue to the world in a meaningful way. He calls it a core feature of mental health, linked to a sense of agency, gratitude, peace, contentment, and delight.

Freelancing gives me this outlet for creation.

Instead of following someone else’s playbook, you get to experiment, add your weird touches, and create in ways only you can.

#4: You gain a sense of agency

In my short 5-year career, I’ve had three separate occasions where I’ve built my income from zero to sufficient (to live & pay rent in a major city) in less than 60 days.

→ In 2020, when I took freelancing projects immediately after graduating college (COVID year, no jobs).

→ In 2022, when I was laid off after my short stint working at SelfDecode (they grew their team too quickly, and our marketing department was first to go).

→ In 2025, when I decided to restructure my business in a way that would give me more agency (instead of contracting gigs with hourly rates).

This gives me an incredible sense of agency over my life and confidence I wouldn’t have if I only relied on outside factors to pay my rent.

#5: It can be more fun

Derek Sivers writes: “When you make a business, you get to make a little universe where you control all the laws. This is your utopia.”

Building a freelance business means you can build it however you want…

> Work with the people you love to work with.
> Find the intersection of your work & your interests.
> Experiment with weird, fun ideas.
> Structure your day around things that energize you.

For me, that may mean a mid-day hike some days. Or working on a personal creative project before diving into client work.

But it’s something I have to remind myself often: You have the power to make this enjoyable.

#6: You’re forced to fail

Failing as a freelancer is both inevitable and valuable. Not failing is a sign you’re playing it safe.

Most “failures” aren’t catastrophic, though it may feel like it. It’s all data to help you refine your process.

Every “no”...
Every botched client call…
Every offer that flopped…

Reveals something specific you can improve. It’s a process of iterating toward something that genuinely works… both for you and for the market.

And if you’ve never misstepped, that may be a sign you’re walking a road that’s too smooth to lead somewhere new.

#7: It makes your market value clear

Freelancing forces you to face the truth about your market value. You only get paid when you deliver something people truly want.

Another great Derek Sivers quote:

“Money is nothing more than a neutral exchange of value. If people give you money, it’s proof that you’re giving them something valuable in return.”

As an employee, it’s easy to believe a paycheck comes just for showing up. Freelancing kills that illusion fast.

You’re not “getting” a job, you’re making a contribution. And the market decides what it’s worth.

That shift changes everything. You start asking:

• What unique skills do I bring?

• What real, concrete impact does my work have?

• Where does my value align with what people will pay most for?

Freelancing teaches you that you’re not just trading hours for dollars, you’re trading value for value.

Closing thoughts

Freelancing doesn’t have to be this transformative journey. It can just be a way to make money without a boss breathing down your neck.

But if you let it, freelancing can become much more:

> A mirror that shows you who you really are.
> A test lab where failure turns into growth.
> A practice ground for building a life on your own terms.

At its best, freelancing is a path toward self-knowledge and intentional living.