#16 A roadmap on how to start freelancing from scratch

  • x6 steps I’d take if I had to start over from zero.
  • Why “overnight success” is unhealthy bullsh*t.
  • The x1 thing to do first, if you can’t do anything else.
How to start freelancing from scratch
😍 Something I'm grateful for this week

A friend of a friend called for advice on what I would do if I had to start over freelancing from scratch. Here's what I told him:

He felt stuck in a rut, he was fed up of his day job, he’d already tried several side hustles, he had dozens of ideas of things he could do, or that people told him he should do, but no idea of how to proceed or progress.
It’s a very difficult position to be in, to have to make a choice but not know where to go. He was in a lot of mental pain about it.
He had heard about my journey and wanted to do something similar.
He wanted to know what I would do if I had to start again from scratch.

So he happened to call me midweek, I’d taken some time to myself and I was marching up a hill with the dog.
I’ve edited the transcript to shorten and remove my out-of-breath panting, tangents and waffling.

Firstly, don’t burn your bridges too early, I wouldn’t go quit without a secure income lined up, but I wouldn’t wait to start side hustling either.
You can make a huge difference in six months to a year, but obviously, as with anything, the change is a trajectory.
You want to start growing your sidehustle as soon as possible.
When I made my first £50 as a freelancer, the word “sidehustle” wasn’t really a word yet.
Nowadays Sidehustles are commonplace.

Most small business owners don’t want to accept it but the wages just aren’t enough anymore.

It’s nuts, Inflation is through the roof. Corporations are out of control, raiding the world like a Mongol horde. Living costs are skyrocketing.
Many small businesses simply can’t afford to pay the amount of money people need nowadays to grow a savings pot.
People are scraping by instead of saving.

But it’s not just that, during lockdown I think a lot of people had a glimpse of what life could be, if we weren’t stuck in an outdated model of work.

In Design Hero I take x5 enquiries a week from people working full-time who want to start a side business,
and they tell me their motivation is financial security and increased freedom.
I’m starting to believe a side hustle is the norm rather than the exception.
Most people ARE freelancing and side hustling.

Give yourself options:

If you’re at the point where you have choices of wanting to quit or being able to quit, you don’t want to be in a position in four years where you’ve got to start growing it from scratch.
If you find yourself in this situation, then it’s going to take you years, you will have to work a job you don’t enjoy, and you’ll feel pretty bad about it.
So I would say the earlier you can start growing your side hustle, the better.
If you can grow your side hustle to where you are earning as much as your full-time job and you don’t need the work.
It puts you in really the ideal position to quit, while still having a secure income.

If I were to start freelancing again from scratch, there’s not really one route or formula that fits everyone.

Every week I speak to freelancers, and I always find it fascinating hearing their stories.
The plan we have for ourselves rarely matches the actual path we take in life.
It’s easy to look back and see my path as a series of decisions that led me to where I am.
But that’s ego talking.
In reality there was a lot of reacting, a lot of second-guessing, a lot of mis-steps and chance involved.
I very easily could have become a starving writer, or a hardcore coder, or any number of other careers, but for a few tiny chance circumstances in life.
There is no ONE correct path. I do think I would always have worked in a creative field of some sort.

The other day I read something by Derren Brown explained this best:
He describes life as a diagonal:
We’re told to set grand goals with tangible numbers attached. We think life will go one way, but life gets in the way then we feel like a failure.
Anyone who has tried to accomplish anything great will probably agree.
But our life follows a diagonal path between our aims and circumstances of random chance outwith our control.
Instead we should try set a general direction instead, and be happy to “split the difference” and enjoy the diagonal.

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My own path definitely reflected this:

I studied product design.
In a previous life I used to be an architect.
I quit that to do web design full time.
Then I got into digital marketing and grew my sidehustle into a solo business.
Between those things were a lot of difficult choices, a lot of second guessing, a lot of agonising.

So I took a very roundabout route into my current life.
For many years I worked like a dog just trying to get ahead of the 9-5.
Like many freelancers, clients ruled my life.
I had a side hustle in the evenings and weekends but for almost a decade my sidehustle made almost zero money.
Certainly you could speed that process up a hell of a lot by gaining the knowledge more quickly, and making the right decisions earlier.

If I were starting again, here’s what I’d do,
This is purely from a “growing your sidehustle” point of view.
There’s more stuff I’d do in terms of lifestyle design, for sure.

Ok, I’ll explain that a bit more first as a bit of a warning about chasing only money…

There’s plenty of people online giving advice about how to make more money.
I followed all the common advice online. And it worked, sort of…
But when I first hit £10k/m I was miserable.
I was totally burned out and left asking “what next?…do I just do more of the same?”.

What happens AFTER you have enough to live comfortably? What happens when you hit your target?
You’ll set another, even higher target and keep working to make more money. Money you don’t even need, to reach yet another arbitrary target.
But wait…didn’t you start this whole thing because you wanted to work less, and have more freedom?

So “enough” money to live comfortably is different for everyone.
But once you have enough money, time is more valuable.
You’ll have time to think, to play, to explore.

But even time has it’s limits.
Once you have enough time, you’re going to get kicked in the nuts with an existential crisis.
It sounds great. It is great! It’s a much better problem to have than worrying about money.

But still, it’s a painful problem to have:
“Why am I working more if I don’t need to anymore?”

So now you’ll need purpose.

But of course, this all sounds pretty lofty, I don’t mean to sound wanky. 🤣
You can’t be worrying about your higher purpose if you don’t have the safety net of enough money to live comfortably, and enough time to think about it.

So for the stage you’re at, where the goal is just to build a more stable income as quickly as possible…

Here’s what I’d do if I were starting freelancing from scratch….

  • Identify my current skills
  • Identify or learn a complimentary skill that multiplies value
  • Identify problems people have that my skill can solve and craft an “offer” that solves the problem
  • Start writing about the problem and the solution online
  • Practice your sales skills
  • Pitch and sell your offer online until you have enough money to live comfortably.
  • Use money to buy back your time (systems, software, team)
  • Use your time to hone your skills, your offer, your process.
  • Once you have money to live and time to think, figure out your higher purpose.

Some other thoughts and soft skills that are critical:
This involves nurturing some new habits in your life.
But personal growth = income growth.


If you only do one thing, then read.
Reading will open your eyes to what is possible,
Reading will change your mindset, and give you new ideas, and the best bit is that everything you learn, benefits you x3, or x5, or x10 times as the things you learn apply across multiple disciplines.
Set aside time every day to read. Read, then read some more. Read like a mofo.

Make it a habit. Read every day for 6 months, even if it’s only 10 mins a day.
You won’t even recognise yourself in 6 months.
As you grow, your skills grows, your value grows, and your income grows.

I read about sales, human behaviour, psychology, offers, lead generation, advertising, philosophy, business strategy and more.
Here’s my reading list


In school I was bullied hard because I was short, I liked sci-fi and I had hobbies outside football and drinking.
But those hobbies became valuable skills. I enjoyed drawing on Photoshop. I made logos for bands and family friends.
Eventually a friend of a friend paid me to do it.
That’s how I made my first £50 as a freelancer, though the word “sidehustle” wasn’t invented yet.
It would take more than a decade, but that £50 would one day turn into a £10k/m solo business.

Almost everyone has at least x1 skill they could sell online.
If your skill is a physical skill, is there a way you can turn it into knowledge or a virtual product?

If you’re selling the same thing as everyone else, then the only thing to choose between is price, and your customers will choose the cheapest.
That’s why there are plenty of freelancers on Fiverr all selling their services for rock bottom prices.
That’s why x1 skill isn’t enough.

Write down all your skills.
Pick x2 overlapping or complimentary skills that complement each other and focus on getting good at them.
This is what will set you apart and give you your unique edge.

  • lego + animation
  • real estate + finance
  • web design + SEO
  • Mountain biking + video editing
  • music + mixing
  • motivational speaking + fitness
  • cooking + wild food foraging
  • construction + interior design
  • woodworking + glassblowing
  • Project management + networking


Ditch all the sidehustles, crazy schemes and business ideas. You only have time to build one great thing.
Ignore the “get rich quick” schemes.
Ignore courses about Etsy shops, selling tshirts, dropshipping, luxury watches, and all that magic pill bullsh*t.
Those courses are mostly built by scammers trying to rip off people in your painful position.

Be wary of shiny new objects. the most common mistake I see my students make is jumping from interest to interest, buying a few courses, finding out it isn’t all sunshine and roses, getting bored, moving onto something new.

Everyone is seeking their “Ikagi” or perfect purpose.
Certainly working on something you enjoy and love is much more rewarding.
But you won’t love it all the time. Life isn’t so neat. Every vocation has paperwork, and admin, and bad sides.
Identify a problem you can solve with skills you have.
Start writing content around the problem your skill solves and publish online to build your authority.
Reading gives you new perspectives and new thinking. Writing reinforces your thinking.


Engage online with the people having that problem.
Offer help, and start selling your skills online.
Be prepared to work for little reward for a long time.
Once you have money coming in the door, combine it with your second skill to improve your offer and add value.
Try to focus on selling a result instead of a service.
Instead of just being a builder, do the planning, the project management, sourcing supplies etc.
Instead of being a celebrant, offer a complete wedding package, the planning the admin etc.

Do the work

Ideas lead to more ideas.
We all have a different amount of time and different situations.
You might only have a morning, or the evenings, or just a lunch break.
You may still be working full time so time is your biggest bottle neck.
Don’t waste it.
There’s too many things to do.
Overwhelm will be a huge problem. This is normal.
Identify the large goals,
But break them down into one tiny action you can take every day.
You can only do what you can do and we all move at our own pace.
If your goal is to make £3k/m, focus on making x1 15min sales call every day.
If your goal is to invest in property, focus on setting aside £150/week.

Prepare to fail & keep going

It might look simple here, but simple doesn’t mean easy.
Be aware each of the steps I’ve described above requires months of work, self-doubt, learning and personal growth, which is always a bit uncomfortable.
If it were easy, everyone would do it!

You’re going to fail. a lot.
But no-one will even notice.

In the West our culture teaches us failure is to be avoided, or is embarrassing.
Failure is a part of the process and teaches us a lesson.
Don’t give up too early before your efforts take fruit.


In truth, the perfect linear path I’ve described doesn’t exist.
You’ll have to try and learn new skills.
You’ll probably need to try things only to find out they aren’t for you.
Or life will throw you a curveball and you’ll have to do things you don’t want to for a while,
Or it might take longer as you have to overcome the obstacles and diversions.

You have to be willing to work for a long time for no reward, so get used to enjoying the process instead of the endpoint.
Patience and persistence is a superpower in today’s world of instant gratification.

The path is different for everyone. Don’t get caught up on the perfect path,
set aside time to work on your sidehustle everyday and keep consistent.
That’s it, I’m sort of rambling now Sorry I’ve been talking a lot,
but I hope that’s helped!

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If you're at the start of your freelance journey, knowing what to do next can be overwhelming. I've created a roadmap of the x5 things I'd work on first..

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💡 Key Insights for solopreneurs

Most people want the quick win, the magic pill, the silver bullet.
Most people aren’t willing to suffer many defeats and keep trying.
People like to rewrite their stories as a neat, short narrative for social media.
But almost every “overnight success” you see, actually started 10 years ago as a hobby or a sidehustle.
Real success isn’t unique ideas or genius or willpower,
Real success is strategy + consistency + time.
It can be boring and hard and slow but that’s what’s required if you want to build a new life

🛎️ Daily reminder for solopreneurs

If it were easy, everyone would do it!
You’re going to fail. a lot.
But no-one will even notice.

💥 How to take action in the next 5 mins

Write down the big actions that need to happen.
Break those down into steps you can repeat daily, weekly etc.
Set aside time in your schedule to do them on repeat.
Do them on repeat.

Picture of Nicholas Robb

Nicholas Robb

Founder, Design Hero
Author of Life by Design

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