How to be a freelance copywriter when you suck at doing what freelancers are “supposed” to do

Back in 1949, a psychologist from the University of Wisconsin set out to study primate behavior.

Harry Harlow and a couple of his colleagues set up an experiment.

Mouse trap images
Source: Drive by Daniel H. Pink

They got some monkeys together, prepared a simple puzzle, put the puzzle in front of the monkeys and watched the scene unfold.

The scientists expected the monkeys to show disinterest.

But when the monkeys saw the puzzle, they began solving it. Immediately. With zero treats or incentives.

Over the next 14 days, Harlow and his team watched the monkeys problem-solve away their days.

Instead of losing interest and wandering off, the monkeys kept getting better and faster.

That’s when Harlow proposed a theory:

What if monkeys – and their distant relatives – actually found problem-solving intrinsically rewarding? And what if people found challenging, engaging tasks fulfilling and would happily do them not because they had to, but because they wanted to.

The scientific community thought both Harlow and his theory were ridiculous.

Humans? Motivated by work? Please.

Everyone knows you’ve gotta dangle the fear of punishment and the desire for payment over their heads. Otherwise they turn into good-for-nothing slobs.

So Harlow didn’t bring his observations up again. He wanted a career and going against the scientific consensus meant its certain death.

But a theory of this magnitude wasn’t destined to die.

Over the next decades it would be picked up by others, tested in companies like Intel, and go on to drive the structure of tech darlings like HubSpot, Basecamp and Google.

But we’ll get back to Harry Harlow (and how his ideas affect your business) in a moment.

First, let’s have a quick chat about the question every adult in your social circle felt obligated to ask when you were five:

What do you want to be when you grow up?

Mom, when I grow up,
I want to be a business owner

I didn’t.

I wanted to be a fighter pilot. Then for about five solid years, a vet. Eventually, I became an archaeologist.

And because archaeological fieldwork (the fun stuff) destroys your body by the time you hit thirty, I opted for the less-deadly option of freelance writing instead.

I hated it.

Not the work itself. I loved that.

I hated being a freelancer. I didn’t want to drink mimosas, work from anywhere or give up and go in-house.

I wanted to be more…

To be a business owner.

Like Harlow’s monkeys, I wanted something that challenged and excited me.

Can I be a business owner please?

Technically I owned a business.

I’d registered an LLC with the state of Texas at the start of 2016.

But I was acting like an employee, spending my days on client work alone and not investing time or resources into growing that business.

According to a survey by Clockify, a time tracking tool, I wasn’t alone: 38% of freelancers spend less than 2 hours a week promoting their business.

I was sick of simply freelancing and yet I was reluctant to join the business owner camp. Because growing my business would mean shifting my priorities and making painful changes.

It would mean investing in myself.

And this idea terrified me.

So if you’ve ever found yourself thinking:

I want to do more than just freelance. I want to own a successful copywriting business that’s demanding and exciting and scary.”

Then this post is for you.

I’ve been consciously transitioning from freelancer to business owner since July 2018. Even in these short four months, there have been plenty of struggles.

Surprisingly, the majority of them were self-inflicted.

The crippling fear when I got in touch with three of my best retainer clients and told them that, from January 2019, I won’t be taking any paid content writing work on because I was focusing entirely on conversion copy and strategy.

The gut-wrenching panic of freeing up two full days a week to focus on growing my own business by investing time in writing long-form blog posts, planning webinar and podcast pitches, creating new products, building relationships and setting up funnels.

The myriad of tiny deaths my ego suffered every time I decided to ask other smart people for feedback on my ideas and offer feedback in return…

None of this felt good.

But it helped me get on the road I want to follow.

I didn’t do it alone.

My transition from freelancer to business owner is largely thanks to the books, studies, and individuals that helped me develop my own personalized framework- the same one I’d like to share with you in this post.

1. All the treats in the world ain’t enough

It all started the day I met Daniel Pink. Drive Cover

Well… “met” probably isn’t the right word. He introduced himself to me through the pages of his book “Drive”.

You know when you read something that confirms your deepest suspicions about the way you work? The ones that you’ve half voiced over a pint at the pub but otherwise safely tucked away.

Pink pulled these right to the surface by bringing me face to face with Harry Harlow, the monkey man from earlier, and the psychologists who picked up and built on his theories: Edward Deci, Daniel Kahneman, Amos Tversky, Mihaly Csikszentmihalyi.

Because the theory that human beings are motivated to do work for work’s sake – if that work is interesting, engaging and meaningful –  refused to die.

Why use monkeys when you’ve got students?

Twenty years after Harlow’s experiments, recent graduate Edward Deci decided to follow in his footsteps, sidestepping traditional thinking once again.

Deci ran a series of experiments using college students and a Soma cube.

soma cube imageA modern Soma cube on Amazon

He split the students into groups and ran the experiment over three days. On day one, students were given the puzzle and a few shapes printed on a piece of paper. Then they were asked to solve it.

Halfway through the experiment, Deci went out of the room under the pretext of entering some figures into his computer. He told the students they can do whatever they wanted while they waited.

On day two, Deci paid one of the groups for every solved puzzle. Again, halfway through, he left just like last time. Then on day three, everyone was back to solving puzzles for free.

The results were intriguing.

The unpaid groups spent most of their “free” time playing with the puzzle throughout the experiment. But on day three, the paid group lost interest. They played with the puzzle for considerably less time than the unpaid groups. 

Deci noticed this:

It [the money] encouraged them to try to solve the puzzles, but it robbed them of the desire to engage in this playful activity for its own sake. 

How monkeys and puzzles relate to growing a business

The Soma puzzle led Deci to start researching two types of human motivation: extrinsic and intrinsic.

Extrinsic motivation taps into your immediate wants and needs. More money. More food. A place to sleep. The admiration of others. It’s an external driver that nudges behavior.

Pink sums up the way we did (and still do) things perfectly:

For as long as any of us can remember, we’ve configured our organizations and constructed our lives around its [external motivation] bedrock assumption: The way to improve performance, increase productivity, and encourage excellence is to reward the good and punish the bad. 

Intrinsic motivation, on the other hand, taps into your internal desires. It’s not trying to lead you with a carrot or hit you with a stick. It’s there to draw on the things you (not someone else) find meaningful.

HubSpot‘s famous 2013 Culture SlideShare is an example of a company using intrinsic motivation to hire their team.HubSpot culture slide - image


Instead of saying:

You should do this because we offer you a great pension, a salary and a stable career.

They said:

Here’s a decent amount of money so you don’t have to worry about the bills. A good leave policy so you can see your family. A contribution towards your future because you’re worth it.

But we know that’s not enough for you- you want to build things that matter. So here’s access to other smart people who’ll challenge you and a chance to build something you’ll love. And if you want in, we’ll trust you to be all in. We’ve got your back and you’ll have ours. 

They tapped into people’s intrinsic motivation- the desire for meaningful work- and reaped the benefits.

Elementary, my dear copywriter

Sherlock Holmes

Sherlock Holmes is the original intrinsically motivated entrepreneur.

If we ignore the opium use (it was the 1800s…) Holmes is an accurate representation of the driven conversion copywriter, eager to carve out a space for themselves.

He created his own job title: consulting detective. Found his own clients by building authority. Always went above and beyond. Chose work that challenged his mind and created meaning.

Deci theorizes that it’s intrinsic motivation that drives the entrepreneurial behavior we need to build a successful, satisfying business.

In his book “Why We Do What We Do“, he sums up why extrinsic motivators aren’t all that:

[Rewards turn] play into work and the player into a pawn. 

Extrinsic motivation introduces an external driver. Something to rebel against.

Because no matter how appealing the reward, it’s got a hidden cost. One that says: If you want this, you gotta give up some freedom. You’ve got to play the game my way. 

Intrinsic motivation, on the other hand, can walk hand in hand with the same rewards that extrinsic motivation gives you without the negative impact.

HubSpot’s culture may be driven intrinsically, but the company is still profitable and growing. It’s a business, so it’s optimized for making money. As it should be. It’s just optimized to do more than that too.

This got me thinking:

As a freelancer, my motivation was mostly extrinsic: money in exchange for a job well done. And it left me feeling empty.

As a business owner, however, I could leverage my intrinsic motivation and be more than just another writer.

But first, I’d need to get past some arbitrary constraints.

Some limitations increase creativity, but this one kills it

Too many arbitrary rules can stifle intrinsic motivation.

Sam Glucksberg from Princeton demonstrated just how much in the 1960s.

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Glucksberg ran a variation of the candle test.

In the candle test, you’re given a tall candle, a box full of tacks and a box of matches. To complete the test successfully you need to attach the candle to the wall. Glucksberg tested whether offering people money for solving the problem will improve the time it took.

Here’s what he found:

Offering a monetary reward increased the average time it took to complete the candle test by 3 and a half minutes.

I’m going to let that sink in for a moment.

People who were offered money to solve this problem sat in a room, staring at a candle, a box full of tacks and a box of matches for three and a half minutes longer than other participants before tipping the tacks out of the box, placing the candle in the box and using the tacks to secure the box to the wall.

Glucksberg discovered that offering an external reward increased linear thinking and decreased out of the box thinking. Yet creative problem solving is essential for most common business challenges you’ll encounter.

Take a common challenge like lead generation.

Imagine you joined a competition. To win, you had to get 20 high-quality ready-to-buy leads in 10 days.

What kind of thinking will help you get there: linear or out of the box?

Let’s follow these two diverging paths a bit further.

Linear thinking is likely to send you down the well-trodden path with your blinkers on. You’ll follow all the pre-established rules, scour the internet for best practices, and try to get there using the traditional way.

But what could happen if you stepped off the road and thought around the problem?

That’s how Garrett Moon, co-founder of CoSchedule, started building up his first piece of software in the middle of the night. Or how Laura Lopuch used cold emails to grow her freelance business 14 times over. And it’s also why Chanti Zak uses quizzes for lead generation when everyone else is too busy creating guides.

They didn’t look at the problem as a linear equation. Instead, they looked at the assets on hand and leveraged them.

As business owners, we are solving problems almost constantly. If extrinsic motivation increased the time it took to stick a candle to a wall, what kind of damage is it doing to our day-to-day?

Here’s what happened when I tied myself to my desk

When I first started freelancing, I had no idea how to set up my day. So naturally I asked Google.

The articles I found came in two flavors:

  1. I work in a serious copywriting office with strict boundaries and a door. I make serious copywriting money. And I wear pants every day.
  2. I sit on a beach drinking fruity concoctions with umbrellas in them. I make some money and I’m all free and bohemian. Pants are for losers.

Clearly, I wasn’t the second kind. So I made myself sit in my office, 9 to 5 Monday to Friday.

This did not go well.

My self-imposed schedule made me hate my work, my office, and even weekends (because why have fun when you can feel guilty about not working!?)

As I kept reading more and more of Edward Deci’s books and papers, my hatred for set hours finally came to a head.

That, and something Joanna Wiebe said. Something that Todd Herman said to her at a moment she needed it.

It’s ok to work weekends. 

Loud bangs started going off in my head. If it’s ok to work weekends, then why wouldn’t it be ok to work at random hours?

I work better in sprints. I’ve tested this.

I’m at my best between about 8:30-1:00 then again between 6:00 and 11:00pm. The mid-afternoon is a dead zone for me. My brain stops working and I transform into a zombie.

Turns out, I’m not alone.

Where productivity goes to die

You know who’s really dedicated to their work? Doctors and nurses.

Yet here’s what happens at hospitals around the country between 2 and 4pm:

Patients are three times more likely… to receive a potentially fatal dosage of anesthesia and considerably more likely to die within forty-eight hours of surgery.

Gastroenterologists… find fewer polyps during colonoscopies… so cancerous growths go undetected.

Internists are 26 percent more likely to prescribe unnecessary antibiotics for viral infections, thereby fueling the rise of drug-resistant superbugs.

Daniel Pink refers to this period as the trough. It starts about 7 to 8 hours after you wake up and lasts for a few hours before you perk up again in the evening.

And this seems to happen for most humans in most countries regardless of gender, race or nationality.

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We feel awful during the mid-afternoon. As a result, our decision-making abilities and attention spans are severely impaired.

So what do you do when your best asset turns into something out of The Walking Dead for a set period of time every day?

What would a CRO do with data like this?

If your daily schedule was an underperforming piece of copy, you’d optimize it. You’d consult the copywriting formulas, check your swipe files and adapt a strategy to suit the client’s goals.

So that’s exactly what I did. I took a look at my freelance business’s best asset (me) and created a schedule around my peak performance times. And here’s what that resulted in:

  1. I gave myself permission to take a break mid-afternoon and work again in the evening. Plus, I now work weekends when I want to. (It’s weirdly fun.)
  2. I split my work into chunks ranging from 15 minutes to two hours. Instead of imposing a sit-down time, I check in with my energy levels and decide. If at the end of a 20 min session I feel like working more, I keep going. And if I need a break, I take it, then get right back to work.

When do you produce your best work?

And conversely, what are your least productive times?

Do you work better in marathons or in sprints?

And if you could design your own ideal work schedule, what would it look like?

If you are not sure, Pink suggests a simple exercise in his book “When: The scientific secrets of perfect timing”:

Track your behavior systematically for a week.

Set your phone alarm to beep every ninety minutes. Each time you hear the alarm, answer these three questions:

  1. What are you doing?
  2. On a scale of 1 to 10, how mentally alert do you feel right now?
  3. On a scale of 1 to 10, how physically energetic do you feel right now?
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It’s your duty to keep your top performer
happy and productive

You are the number one asset your business has.

If you are not at your best, everything suffers.

It took me a ridiculously long time to begin to grasp this idea. And then to give myself permission to actually do something with it.

When I finally optimized my work schedule, I began producing better work. Not just that, I consistently created more.

But even with an intrinsically optimized schedule, something still wasn’t fully clicking because I lacked clarity.

That’s when I bumped into Steven Reiss.

2. One size fits all

Have you ever tried one of those one-size-fits-all hats?

My ego likes to think I’ve got a normal sized head. But if I judged my head based on those hats, it’s to normal sized heads what Jupiter is to Earth.

So if this doesn’t work for hats – something much more likely to fit multiple people than shoes, jockstraps or best practices – why should it work for anything else?

And yet one persistent myth that embodies this ridiculous idea refuses to die:

High performers get up before dawn.

Discovering 5am existed changed my life (but not for the reasons you think)

Five o’clock in the morning changed the life of this person. And this person.

This guy even wrote a book about it that convinced a whole new generation of early risers that mornings are best.

image of glowing review on amazon

Just 1 out of 2587 glowing 5 star Amazon Reviews

One of the people I love most in this world is a morning person.

She wakes up at 5am naturally.

And she spends the rest of the precious morning wondering why the rest of us are still asleep.

Well, I’ve been up at 5am. Consistently. The year after college, I worked in management at a grocery store. Most mornings, I opened the store at 6. You know what I discovered about myself?

That I’m useless to the world in any brain-functioning capacity before exactly 7am. (It’s the morning equivalent of the mid-afternoon trough we talked about earlier.)

And it doesn’t matter how much coffee I down. Or how early I go to bed.

Before 7 am

It’s like clockwork.

I can do sleepy person things like move cages loaded with food, make bad puns or do paperwork.

But actual problem-solving? Conversion optimization before the clock strikes 7?

Unless the fate of the world hangs in the balance (or I simply haven’t gone to bed yet) I wouldn’t count on it. And even then, it’s probably best to wait a couple of hours just to be safe.

Staying up until 5am though? Totally different deal. I love working late at night. It’s calm and peaceful, and I get my third wind around 10pm.

This doesn’t make morning people wrong and me right. It just means that their best practices won’t work for me.

No time like night time

Andrew Wilkinson is a badass. He is the founder of MetaLab (the agency that designed Slack and Coinbase) and project management platform Flow. On top of that, he’s an angel investor and the publisher of Designer News – and he does way too many other cool things.

But those are not the most interesting things about him.

Wilkinson wakes up around noon and works for 5-6 hours in the late afternoon. When he needs to, he works for a few hours late at night.

It wasn’t always this way. He tried working 80 hour weeks, not getting much sleep and spending all his time at the office. But paradoxically, this led to a decrease in performance. Optimizing his schedule, on the other hand, led to optimizing his work processes.

He’s not alone.

J.R.R. Tolkien liked to wake up at noon and work late into the night. Pulitzer prize winner Kathryn Schulz does her best writing in the middle of the night.

And while those are great examples, don’t let them sway you. Staying up all night probably isn’t the secret to success either. But discovering your own optimal schedule might be.

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Can someone please tell me what I should do with my life!?

Psychologist Steven Reiss doesn’t talk about the superiority of morning people. Or evening people.

Reiss theorizes that to feel fulfilled, a person needs to live their life in balance with who they are. Otherwise you are setting yourself up for a whole lot of misery.

He suggests that who you are is a unique combination of sixteen basic desires found in all human beings and observed in most mammals.

Reiss list...
These definitions are a direct recreation of the ones used by Reiss on pages 17-18 of “Who am I?”

Everyone experiences each of the sixteen in a strong, weak or average way. And because these sixteen basic desires can be combined in trillions of different ways, their interplay helps shape your character alongside your environment.

Me and you, we aren’t exactly the same…

Think of someone you really like yet regularly clash with. You just don’t understand why they make certain life choices.

Sometimes it feels like you are talking a different language. Maybe you are.

Your desire profile affects how you communicate with other people. You may find that you communicate instinctively and fluidly with people whose desire profiles are similar to yours.

That’s why it often feels like there’s an invisible wall between you and the people who don’t understand the business you want to create. No matter how much you explain it, they don’t get it. And you don’t get why they’re wasting their time doing menial work to line someone else’s pockets.

I didn’t fit the desire profile of the traditional freelancer. I don’t perfectly fit the mould of the ideal entrepreneur either.

And so the best practices and hacks just weren’t working for me.

Luckily, Reiss provided a few simple exercises to help me figure out my own profile by digging into what each desire looked like.

Here’s what the curiosity example looks like and my response to it:image with yep yep yep

Using the exercises, I began building up a profile of what’s important to me and what isn’t.

Unsurprisingly (to myself) I rated high for power, independence, curiosity and idealism, average for order and on the lower end for status.

Finally I had a solid explanation why building a unicorn business everyone knew about or showing up everywhere on social media just didn’t appeal to me:

Money and status weren’t strong enough to drive action for me.

I liked money well enough – anyone who’s grown up dirt poor instinctively understands its importance – but it didn’t motivate me.

Sure, I wanted to make a lot of it. But that’s because making money meant the ability to be self-sufficient, to push myself to build a business that fascinated me and to give back.

What are the things that drive you to build a business? The tendencies that are an irrefutable part of your makeup?

Because working with them can make building a business simpler. I know it did for me.

I dug through the muck, past the stories I told myself about my life and what I wanted and all the way to what I actually wanted. 


“As times goes by, you have a relentless tendency to be you.”

At the heart of Reiss’s hypothesis is this:

You are your own person. Therefore, you need to adapt existing best practices and other people’s ideas of what you should do to match who you are.

You need to develop your own framework for success.

This is exactly what conversion copywriters and CROs everywhere tell clients.

We tell them that just because a formula, structure or best practice worked for someone else doesn’t mean it will work for them.

We say:

You should test it. We can’t guarantee results because your audience is different. Because the context is different. Because nothing in the world is static.

Reiss showed me the need to dig through my own layers. Through the things that deeply mattered to me as a person, as a copywriter, as a business owner. And the things that didn’t.

Understanding some of what drove me slowly began to reveal the things that I wanted to achieve.

There was just one big hurdle left:

I was terrified of falling flat on my face.

3. The unexpected ally that always has your back

Deci and Reiss opened up a door. But it was Brandon Webb and his latest book, “Mastering Fear: A Navy Seal’s Guide” that helped me step through it.

Fear is awareness of danger. 

This Navy Seal turned entrepreneur isn’t a psychologist.

And he doesn’t spend his days in a lab or a library, creating theories.

Webb runs Hurricane Media, a military-focused digital content network. He grew the company from a blog – starting it after his first business exploded and lost investors a lot of money – into a 100+ million dollar company. And he’s accelerating.

Unlike Deci and Reiss, everything Webb writes is deeply practical. It’s tested in the harshest environments and re-tested in the world of rising and falling startups.

He takes hard-to-implement phrases like:

  • Control your interior monologue
  • Make fear your ally
  • Learn to trust your gut
  • When opportunity comes, seize it

And then shows you how to actually do those things with step-by-step’s and practical exercises.

Because more than anything else, Webb’s advice is relevant to us: The entrepreneurs building the little businesses that could.

What happens when you come face to face with everything you’ve been avoiding?


I don’t know about you, but fear has been a pretty consistent companion for as long as I can remember.

Did you ever have to sit around a table at school and discuss your fears?

I did.

We were doing a job interview exercise and the teacher went around the room. Every kid had normal, acceptable fears. Clowns. Spiders. Speaking in front of a crowd.

Until me. When asked what my biggest fear was I blurted out:

I’m terrified I’ll fail at life.

Yup. Obviously, everyone looked at me like I was a total weirdo.

But it’s a fear that stayed with me beyond that dingy classroom. What if you fail? What if you try this and fall flat on your face? What if…

I tried a lot of coping strategies. Ignoring it. Pushing it down so completely that it took a lot of other things with it. Feeding it triple chocolate chip cookies.

But none of them proved sustainable long term. Sooner or later, the fear would come back stronger.

Of course, I’d flirted with the idea of embracing fear. But without a proper framework it didn’t really stick.

Until Webb.

Because instead of something that needs to be fought at all costs, Webb casts fear as your most valuable ally. A heroic side-kick who’s actually looking out for you.

The difference between old fears and
what’s in front of you right now

The biggest things that hold me back are the scenes that play out in my head. Spectacular failures like getting shunned by the entire conversion copywriting community for saying something stupid.

But when I read this line by Webb, the various scenarios slowed down for a split second:

The great majority of the fears most of us experience day to day are nothing but shadow-boxing: not a response to genuine danger but a reaction to the reverberation of events long behind us. 

A lot of my old fears – fears I’ve refused to look in the eye – come up every time a situation that looks like their planet of origin crops up.

When you think about fear’s biological purpose, that makes complete sense. It’s there to protect us. If you’re out in the jungle and you see a shadow that looks like the tiger that ate your buddy Billy, assuming it’s a tiger and getting outta there is a smart move.

That’s why Webb advocates using fear as an ally, leveraging its early warning system and using it to power our response.

Building a business is all about working with that fear.

Using it to take that small step forward.

And the next one.

Until you eventually get to where you want to go.

I love it when a good framework comes together

The ideas of intrinsic motivation, an individual approach to life and working with your fears fit together surprisingly well.

They helped me get clear about the business I wanted to create.

But clarity wasn’t enough. All the theory books in the world are worth next to nothing without action.

If I wanted to ditch freelancing and become a business owner, I had to take action. And lots of it.

So let’s revisit the mindset decisions we discussed and take a quick look at the action steps I took to make them real.

1. Optimizing my schedule for intrinsic motivation

Has a flexible schedule made a difference?


Now here’s the long answer:

I’ve been taking on the same amount of client work as before but there’s been a major difference in what my days look like.

Allowing myself to take breaks made the work go by faster without sacrificing its quality. And it created extra time to start working on marketing for my own business like:

As well as a few other projects I’m not ready to reveal just yet.

Simply allowing myself to optimize my work time allowed me to use it better. Because instead of working to the clock, I was now working to the job.

2. Developing a personalized “freelance copywriting” framework

Using other people’s definitions of what I should and shouldn’t be doing got me nowhere.

So after developing a personalized framework I began applying it to my work to:

  • Do thorough market research into the businesses I want to work with
  • Optimize my business processes. This took a lot of small actions like setting up and optimizing workflows using tools like Asana, 17hats and Funnelytics, test driving different tools, and getting the ops end ready for growth
  • Have some hard conversations with clients and condense client work down to 3 days a week so I could spend the others growing the business

3. Embracing fear as an ally

As of writing this post, I’m a month into embracing fear. What does that look like?

Every day, I set myself a couple of small things I’m afraid to do.

Things like:

  • Hit publish on blog posts I’ve been holding on to
  • Film video reviews
  • Post on LinkedIn about conversion copywriting
  • Reach out to specific people in my network and actually ask for help (versus vaguely hinting that help may be good…)
  • Run an idea I’m working on past someone who’s got experience in that area instead of jealously guarding because I was too scared they’d think I was stupid Ask for help

All these tiny actions led to an unexpected outcome. No, it hasn’t gotten easy. Not even a little. But my own internal reaction to failure has shifted. The most recent example happened a few days ago…

I asked some awesome conversion copywriters for feedback on my new home page. I’d spend a couple of days working on it and was pretty proud.

Then I got this comment:

I’d rewrite it.

And this feedback wasn’t from just anybody. It was coming from one of the best conversion copywriters out there.

Before, I would have thrown a hissy (in my head), felt bad, had twenty cookies and put off rewriting the page for the next three months.

But something interesting happened. I kept re-reading the feedback and instead of slinking off to lick my wounds, I started asking clarifying questions.

And then I sat down and rewrote the page right then.

Turns out, the tiny, consistent actions helped build my mental muscles enough so that failing didn’t cripple me.

Because if fear could be an ally, then maybe failure wasn’t all bad either.

Every successful entrepreneur I admired had the uncanny ability to take a hopeless looking situation and turn it around.

Thomas Edison kept pushing until he had a viable light bulb. Stephen King kept searching for a publisher until one finally said yes.

Maybe I could learn to do that too.

Optimize your life as a freelance copywriter like your business depends on it

The biggest lesson I’ve learned so far is this:

If you want to build a business, you need to optimize your processes with your own needs in mind.

Existing best practices and guidelines are a good place to start. They are the equivalent of a great copywriting formula or your trusty swipe file: an excellent starting point.

The current way I structure my days is adapted from a practice mentioned in the Copyhackers’s course The 10x Freelance Copywriter. Splitting my days into morning and evening work sessions was inspired by Talia Wolf. But I wouldn’t have been able to apply this inspiration properly without figuring out my personal best practices.

So if you want to transition from freelancer to business owner, I’ve only got three little words to say to you:

Never stop optimizing.


About the author

Sophia Dagnon

Sophia Dagnon ( writes conversion-focused copy for tech companies. She gets into the heads of customers with strictly non-invasive tactics and uses what she finds to create funnels, emails and landing pages.

  • rishav sharma

    I love this article! I shared it everywhere I could! I’m definitely

    guilty of avoiding cold emailing. Thank you for writing this

  • Lisa Hill

    Thank you Sophia! I’m just getting started as an entrepreneur and you’ve managed to tap right into the things that hold me back. I really appreciated the in-depth sharing and perspective. Cheers!

  • If you’re looking for a specific form of client, tailor your business website and portfolio based on what the client is in search of in a freelancer. This allows you switch out your projects based on the clients’ requirements, showing your capability to work with any form of client no matter what the product or service.

  • Alaina D

    The post I needed! I’ve been through a heavy summer with my fledgling business. My mind and body have created fears that cloud my mind, so I’m ready to invest in those fear-sidekick frameworks you mentioned.

    I also relented and got me a therapist that I’m going to work with for a month just to help me address this seemingly unconscious response to client work. I ended up crying last night because I was putting work off for YET another day because my head was too anxious and cloudy to form comprehensive sentences.

  • Nontas Karavias

    What. An. Epic. Post.
    Thank you.

  • Hi, Sophia
    This is really informative and educative content. Copywriting is one kind of art of writing, is not just write for hard selling and I’m agree with your thought. I’m pleased to read it.

  • Yonatan Hurwitz

    Truly eye-opening, Sophia!
    Thanks so much for sharing your wisdom (and others’).

    I am currently in an in-between phase (salaried employee to freelancer), and it is scaring – and sometimes depressing – the crap out of me. Posts like these help me feel more confident. Thanks again.

  • such a wonderful article. I was like ‘wooooo’ while reading. thanks for sharing.

  • Markus Geisler

    Killer Post Sophia…
    Brilliant thinking and synthesis. Keep up this excellent work. Oh – you might want to check out Sean D’Souza’s Chaos Planning book as well… definitely some common themes. Over at psychotactics dot com, in the products section.

  • Brian Ellis

    Excellent read. At 62 and with a similar rating of curiosity as yourself I’ve got to know what works for me, unfortunately this has often been accompanied by an underlying sense of guilt. Thank you Sophia for an eye opening article.

  • Such a great content representation. I so love the intrinsic motivation ideas, somehow its inspiring and a life changing approach to personal growth. Gotta check those books you’ve mentioned. Nice article, keep posting.

    • Sophia Dagnon

      I felt the same way when I first read about them: it’s just so interesting. Thanks Rebecca 🙂

    • rebeccamatias already

  • Sophia, this article is mind blowingly awesome. The fact that “the trough” is an actual phenomenon makes me feel way less guilty for just wanting to drink a G&T and watch Outlander when 4pm strikes. I tried the 5am miracle morning wake up thing for about 6 months thinking I was being a good little business owner. I was SO unproductive so I’ve since relaxed back into waking up when I feel like it and life is better that way. I love how you relate conversion optimization to optimizing our lives as business owners and entrepreneurs. Thanks for the many insights and reminders!

    • Sophia Dagnon

      Right!? Discovering that “the trough” is a real thing made me ridiculously happy. And that aparantly changing energy levels throughout the day is something completely normal and happens to everyone (as well as most other primates…) I used to feel like such a crappy entrepreneur for crashing in the afternoon.

      I’m ridiculously impressed you tested the 5am thing for 6 months. My test was kinda forced, I’m not sure I’d have survived it on a voluntary basis.

  • Sits in the corner and cheers for my friend! Now the whole world knows how awesome she is 😉

    • Sophia Dagnon

      Thanks Todd 😀

  • Varun

    Great insights, Sophia…Unfortunately many people’s belief systems work against them, and its usually late when they wake up to the harsh realities of “self-optimization.” For starters, we need to question our frameworks and stop double-downing on beliefs over reality. A world class copywriter is a journey of mastering self.

    Thanks for this serious piece of wisdom.


    • Sophia Dagnon

      I love the way you worded that Varun: mastery of any skill really is about mastering yourself. Glad you liked the post 🙂

  • Claire Heginbotham

    Really really helpful, thanks Sophia!

    • Sophia Dagnon

      Glad you liked it Claire! 🙂

  • Nechama Elbaz

    Wow, Sophia. You just turned my world upside down.
    Where can I find Reiss’ exercises?

    • Sophia Dagnon

      Thanks Nechama 🙂

      I got them from his book “Who am I?” It’s a bit 90’s but if you can get past the style the hypothesis is pretty interesting.

    • Thank you for sharing this information, Nice to read and will try to implement the same

  • Patti Haus

    Figuring out personal best practices is something that I’m always trying to tweak. Thanks for putting it into a great resource! I plan to buy some of the books you recommended to help me on this journey.

    • Sophia Dagnon

      Thanks Patti 🙂 It’s hard developing the practices– has been for me anyhow.

      Daniel Pink’s “Drive” is a great place to start: that was what really got me thinking about motivation and optimization.

  • heidicohen

    Thank you for this amazing piece of content. It should be required reading for every freelancers.

    I’ve read a lot of books by people you cite and appreciate how you’ve put then into an easy-to-consume framework.

    Happy marketing,

    Heidi Cohen – Actionable Marketing Guide

    • Sophia Dagnon

      Thanks Heidi!

      Aren’t these books awesome!? I’ve been reading my way through the reference list from Drive and there’s so much good stuff in there (and relevant for marketers).

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