Real FAQs from real freelancers

Hey Ivan, great question!
So it didn’t happen overnight, it was an organic progression for me over many years.
I’ll break down my journey for you:
This is going to be pretty much off the top of my head, unedited and unembellished.

From Fired to Freelancing

Since I was a teen, I have always designed things as a hobby.
This turned into a sidehustle, so I’ve always done my freelancing I guess.
It earned me some extra pennies while I was studying at university.
Later as I went into the world of work I kept doing it as it added to my income. It never made much money, sometimes as little as £500 a year.

For most of my life it was not enough to sustain me as a career.
This is something most gurus online don’t talk about. People aren’t honest about it on social media:
Every time I see a post where someone claims to have quit their job, started freelancing a  years ago and now they earn £10k/m,

I want to shout:

“Did you, aye? BOLLOCKS!”

It’s a harmful myth that makes people feel crap about where they are.
We all have different starting points, different responsibilities and advantages/disadvantages.
But the truth is if you want you grow your own business, if you want true freedom, if you want to escape the ratrace…then it takes many years of working hard for little reward.

Most people aren’t willing to work hard for no return for a few months, never mind a few years.
Every “overnight success” you see is just action + consistency + time.

It took almost 10 years for my side-hustle to earn enough money to sustain me.
Every year, my clients, and my earnings, grew tiny bit by bit. Eventually, it reached a point where I started to glimpse it as a full-time income.
I remember during lockdown I was officially furloughed, but unofficially I was expected to work on the sly.

Around this time I think everyone had their “great awakening” and we all had a glimpse of what life could be, outside the status quo of the commute, the 9-5 etc.
A lot of people had no work to do whatsoever. For months! This blew my mind!
I watched people go nuts. People were drinking more, bored out their minds, addicted to Netflix.
But they also had time with family. Time to get outside during the day and walk in nature.

At the time I resented the fact that I had to work, but in hindsight I think it actually saved me.
I’m not made to be idle. I don’t think anyone is.
So with a little more spare time, I started reading books  by the masters of lifestyle design:

Tim Ferris’s 4 hour workweek, the 80/20 rule, the compound effect, Hell Yeah or Hell No, Free Time and more. you can check out my reading list

I read every day, I read like a mofo, and then I read some more.
This opened my eyes to what is possible.
Most people aren’t even aware of what is possible with the right knowledge.
Read every day for 6 months and you won’t even recognise yourself.
Apply what you learn every day for 6 months and you won’t even recognise your life.

Reading opened my eyes.
I became dissatisfied with the idea of working a 9-5 the rest of my life, of being underpaid, undervalued, constrained in my hours and actions.
It no longer seemed tolerable.
At that point I thought; “if I can just get x2 clients a month at 1k each I could quit”.

It lit a new fire in me, and I remember calling up enquiries on the way to and home from work, and designing logos for £120 on my laptop on park benches during lunch breaks, my hands were so cold I could hardly work the mouse.
I was working pretty hard. I think this is a necessary stage in growing your side-hustle into a career.
But it’s not sustainable. Eventually caught up with me in a big way…

My boss found out I was side hustling and he didn’t like it.
I never hid Design Hero, but I never shouted about it either, for obvious reasons:
Most bosses don’t like their employees to have their own motivations and aspirations outside of the job.
Most bosses expect employees to be 100% loyal and dedicated to putting more money in the company’s pockets, instead of helping themselves first.

But loyalty should work both ways; I was underpaid for the number of roles I was filling;
I was a web designer, coder, project manager, social marketer, SEO and more.
I’d been promised multiple raises, commissions etc for a while, which never materialised, I was getting pretty fed up of waiting already was watching my Design Hero income.
I started wondering if I could make the leap to full-time freelancing.

Then fate made the decision for me:
Some of my work won some awards, I posted it on LinkedIn. My boss found out about Design Hero.
At the time I was working remote from home, and I made the fatal mistake of calling an enquiry for Design Hero during work time.
It was my failure and I shouldn’t have done it. I failed to maintain a proper separation between work and my sidehustle; something I was normally very strict about.
I justified it because I often worked late and overtime for my 9-5. I never asked or expected to be paid overtime for this, working hard is just part of who I am. So I didn’t see any harm in swapping the time and making it up later.

But it was a conflict of interest, he found out and fired me on the spot.
I don’t blame him, he was a nice boss, he was hurt as he felt betrayed and that I was living a double-life. He wasn’t wrong!
I was working full-time and working my side-hustle on evenings, weekends and even lunch breaks. My heart was with Design Hero rather than my full time job.

So he did me a favour and forced me to make the leap.
Looking back now, as a boss myself, I think it’s naive to think that people who work for you won’t also work for themselves.
This is even more true now as living costs outpace the rate of pay.

There’s a certain type of person who is always learning. Who picks up multiple valuable skillsets. Who takes initiative without instruction. Who questions “Why”? Who stays curious, works hard and outgrows their job title again and again.
If you are someone like this, then most bosses at small businesses can’t afford to pay you what you are due and you’re probably destined for freelancing or solopreneurship.
I try to keep this in mind. If my team have aspirations, instead of trying to stop them, or making them think they have to hide it, I teach them, help them, and advise them.

From Freelance to agency owner

I see being fired as a turning point where my income took a quantum leap over a short period of time.
Looking back, I think this route gave me an advantage over other designers:
Because my time was so limited I was forced to work differently:

I didn’t have hours to call clients, to chase enquiries, to churn through the admin, to chase invoices.
I had to work smart not hard.
I thought now that Design Hero was my only job I’d have loads of free time.

But it turns out your tasks expand to fill the time you have. It even has a name: “Parkinson’s Law”.
I reached my first £10k/m and I was miserable. I was totally burned out, and maxed on time.

I was working for myself, I’d reached 6 figures, I’d achieved everything I had everything that I’d strived for.
So why was I miserable?

It was a critical realisation for me:
After you have enough, more money won’t make you happy.

This cliche is so commonplace it’s practically gospel.
But it’s one of those one’ you have to experience first-hand to understand.
Many never earn enough to learn this lesson.
It’s a good problem to have. Certainly better than burning all your time to make enough money.

‘Enough’  is different for everyone. But it’s probably less than you think:
I have a theory most folk would be much happier earning £70k/yr on a 3day workweek than £120k+ working 5 days.
After that point, time quickly becomes far more valuable to you.
You’ll find yourself spending what would have previously been obscene amounts of money, just to buy back your free time.

So I built systems, automations, scheduling, templates etc. to 10x the limited time I had.
Every time I did a task I would spend twice as long trying to figure out a way to avoid having to do it again.
This was the foundation that allowed my business to scale without me putting in more time.

1 year after being fired I had periods where I made more in 1 month than my whole annual salary.
Nevertheless, there’s a limit to how much you can grow by yourself…

By that point, I’d spent ten years building websites, and I had to continue to support existing clients, whilst finding new ones to grow my income.
It became so that I was spending more time on support than growth.
So my first hire was someone to help me with small support tasks for WordPress sites.

This I guess is the first step towards an agency:

Moving from doing everything yourself to having help with fulfilment, so you can free yourself up to work on big picture tasks, growth, sales, systemizing your business etc.

By the next year I’d managed to optimize my business down to a 3 day workweek.

I still prefer not to think of myself as an agency owner.
I still think of it as a solo business, but I guess since I do have a small team,
I’d describe Design Hero as a micro agency for startups.

Yet I have to face the fact that I do have a small team under me,
and I spend more time running the business, building systems etc than I do doing design these days.

It’s a new set of skills to learn, new challenges, new problems.
Life is always learning.
In a solo business, you ARE the business.
So personal growth = business growth.

They say being a manager is watching someone take x10 longer to do the job half as well as you would lol.
But as always you have to think super long-term. If you take the time to train, and to teach, with patience, it pays off in the form of more freedom.
I teach every freelancer as if they were a student of mine, and were paying for my time.

I take the time to review, critique and explain everything I do for them.
I record my work, explain my thinking, outline the strategy, the Why, and the Why nots.
I teach the soft skills like client management, policy settings, boundaries etc, all the difficult stuff that they don’t teach you in design tutorials on Youtube.

From Agency Owner to Mentor

At this point I had enough money to live comfortably. I had systemized a lot of my business so I also had free time.
At first I used this time for leisure.

I hiked, I played video games, I worked in the garden, I took bike trips, and I even did a bit of lifestyle design;
I looked at my childhood dreams and got into motorsport in a small way. It was a great summer.
But I’m not made to sit still.

I started to feel a creeping anxiousness that I couldn’t explain.
I used the Five Whys to work through it to figure out what I was feeling and basically, I found that I was bored.

It’s like video games: When things get too easy, you get bored.
People need a challenge. So I sought my next challenge and took time to think about my life and what I wanted to do.
I sought something which would give me a sense of purpose, of how I could do something with meaning.

Just as I never set out to be an agency owner, I never set out to be a mentor either.

Teaching my team naturally led into teaching other freelancers.
I was already recording training, doing daily teaching and c oaching to nurture my team’s skills.

My freelancers kept telling me that instead of my paying them, they should really be paying me, just for the stuff I was teaching and mentoring.
I wasn’t fishing for complements, several of them said this unprompted. So I thought there was something in that…
I figured a good way to do that would be to help other freelancers navigate the problems I’d already had.

I was already getting questions on social from freelancers on how to solve some of them.
I repurposed my social accounts for my coaching platform, I write every day about running a multi-six-figure business on a 3 day workweek,
and I share the systems and strategies I use every day in Design Hero.

I write about all the problems I’ve had, how I solved them, and how to do it without getting burned out.
(spoiler alert, I still get burned out sometimes!)
But people get value from the content, they contact me to ask me questions, just like this, and I give them answers freely, and then I ask them if they want further help.

That’s how I got into coaching.
It doesn’t make much money.
But I have enough money, it gives me purpose to help freelancers.

I try not to let it become a business;

I write for the sake of writing and nurture the habit.
I treat it the same way as I did Design Hero when it was still a sidehustle:
Instead of focussing on profit, I treat it as getting paid to learn about coaching, and learn my audience’s problems.
I’ve been helping freelancers solve their problems for about a year now.

They bring me their problems, and I give them solutions that have worked for me, and I check-in to make sure they are working through the problem to a solution.
I’ve noticed they often bring me the same problems, and that they often aren’t aware of what the real problem is.
So sometimes I give them a roadmap and framework to go through to…

• Redesign their lives
• Optimize the business for profit & freedom
• Systemize their business as a lifestyle business

So the next step for me is taking my 1-1 coaching and turning the format into a more structured cohort-based course which I’m calling Systemized Solopreneurs;
The goal is to help frantic freelancers redesign their lifestyle, build a 6 figure business around it that puts life first, and systemize it to give them freedom without burnout.

That’s pretty much where I’m at now!
I’m sure there’s more to it that I’ve forgotten, but that’s the broad strokes!

If you’d like help along this journey, reach out for a chat, I’d love to talk to you more about it.