What I Learned in 4 Years of Self-Employment
Clarity, just like mastery, is an outcome of action; it arrives when you are already on the path.
Who is self-employment for?
What skills or qualities does it actually take?
What often gets overlooked?
I reflected on these questions as I celebrated my 4-year Quitting Corporate anniversary recently.
While I reminisced on some of the most important lessons I’ve learned (like how business revenue ≠ what you get to pay yourself…ouch!), I couldn’t help thinking about some of the myths that endure.
Self-employment is certainly not for everyone, but I vehemently disagree with most business media that there is only one mythical “personality type” who can do it.
Over the past 4 years of advising, coaching, studying from and collaborating with many founders and independents (as well as running several businesses myself), I’ve been curious about what is actually required for success in self-employment.
High executive functioning skills? Useful but not essential.
Extraversion? Charisma? I know plenty of thriving entrepreneurs without both.
Always having work on the mind? ("essential" according to Forbes magazine) Well, we all know where that leads.
In my humble opinion, these are the 5 skills to develop and strengthen that almost guarantee self-employment success.
What Does It Actually Take To Succeed in Self-Employment?
1. Imperfection
There is no amount of preparation that will ever have you feeling ready to embark on the journey that is self-employment. The position itself teaches.
Those who triumph are willing to be beginners, to be “bad” on their first try, to be wrong and have to change course, to be wholly imperfect — again and again and again.
Clarity, just like mastery, is an outcome of action; it arrives when you are already on the path.
Over the past 4 years, I’ve evolved imperfectly through trying many different roles and business models: starting as a Social Media Consultant, then becoming a Brand Strategist, beginning (and quickly abandoning) a small agency set-up, then eventually moving into coaching with a few more steps in between.
I gave up printing business cards in 2019 and my website until Year 4 was a messy cohabitation of all these iterations (but I still created clients and sold products without a hitch).
Your clients and customers don’t need you to be perfect in order for you to provide value. They just need you to be one or two steps ahead of them.
2. Self-Awareness
It makes sense that self-employment and self-improvement are so enmeshed: there’s nothing quite like becoming 100% responsible for your own livelihood to make you face parts of yourself you’d rather not.
Want to become the mistress or master of your own destiny? Then buckle up: you’ll be confronting your greatest fears and trauma triggers, the sources of your deepest shame, and where you cling to attachments that don’t serve you.
Self-Awareness means having a clear perception of yourself including:
Your strengths (and how they can blind you)
Your weaknesses (and how they can benefit you)
Your thoughts (and where they come from)
Your beliefs (and their legitimacy)
Your motivations (and whether they’re healthy or harmful)
And your emotions (and how to use them)
Self-awareness is hands-down your best business strategy – it's the difference between those who struggle for years and those who see every obstacle as a way to grow.
Which is why I spend 80% of my time with my coaching clients in this area, and why I created my Unstoppable framework to guide anyone considering self-employment.
3. Intuition
The number one reason new businesses fail? “No market need” according to CB Insights.
🤦🏻♀️
Years ago when I moved in startup circles in London, I was startled by the multitude of aspiring founders pitching ideas that were unresearched, untested and unnecessary.
You don’t need to have an MBA or have attended a fancy accelerator to come up with a lucrative business idea. You DO need to be able to tune into the resonance of the collective to listen for unmet needs and intuit how customers will behave.
This is why empaths make very astute businesspeople. “WOW, you really get me — take my money!” is the happy outcome of intuition, not bravado.
Here’s a mini-course I wrote on how to get people to buy what you’re selling, and the sales process I use that has a 93% close rate.
4. Imagination
Intuition is just the first step, because next you need to imagine manifold possibilities to create what is missing.
Being too realistic is often a hindrance, not a help, in business because limiting your scope to what is already real puts you at a great competitive disadvantage.
No one is going to give you a pre-made plan to follow, or a list to tick off (and if someone tries to sell you one — don’t trust them). You have to invent it all.
Imagination was what saved me from burnout because in order to prevent it from happening again, I had to invent a whole new system for working that I had never seen modelled by anyone else.
As entrepreneur Derek Sivers once said: “When you make a company, you make a utopia. It’s where you get to design your perfect world.”
Here’s a fun exercise I use with my clients to get their imaginations going.
Don’t waste energy fretting about the future.
Get curious about what’s coming.
5. Curiosity
The unpredictability of self-employment is a microcosm for the mystery of life itself. Taking your livelihood into your own hands requires the fortitude to acknowledge everything moves in cycles of gain and loss, motivation and disenchantment, fortune and failure.
You’re never going to know how well your product will sell until you try.
You’re never going to be able to control exactly how even the best-laid plans unfold or stop a big client from leaving at just the wrong moment.
Don’t waste energy fretting about the future. Get curious about what’s coming.
Over time, curiosity for the great unknown can mature into devotion. If you can go to the place everyone else most fears and make a home there, that’s when the magic really begins.
Cheering you on in your journey as I begin year five of mine.
I’m Imogen and as a business mentor and leadership coach, I help people to be more prolific, purposeful, and present in their life and business…without burning out.
If you’d like support in your self-employment journey in strengthening these 5 essential skills, book a free call with me to talk about coaching.
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