"I'll go freelance,": Avoiding the obvious solution
Believe what you read on LinkedIn and freelancing is a golden ticket to freedom.
They're queuing up to tell you (they seem to have a lot of time to post on LinkedIn) how they feel a sense of 'control', 'choice' and 'autonomy'.
I did it. I worked as a marketing consultant for about three years. And I don't buy it. V+-ery few freelancers believe the half of it either. These warriors of independence have become the worst of the lot: flaunting a cappucino in a shared workspace like it's an anti-nazi league flag level of radicalism, charging by the hour to write messages that help one payment software homepage outconvert another, and telling the world that this is self-determination and values-driven: that this is something you should aspire to.
Be Honest About Freelancing
Freelancing is the hype diet that leaves you fatter than before, and wondering why.
Freelancing feels like the easiest option for a reason: it doesn't really change anything.
It's a way to keep one foot in the system while telling ourselves we’re breaking free. And a sign of this is how fervently freelancers will insist: there are no other options. They're victim playing at some pretty low-oxygen levels: after as little as 10 years in a corporate role, their entire human value has been reduced irrevocably to the deployment of three skills in two sectors and one org size.
Freelancers I'm not calling YOU out. But the shaky table leg this whole game rests on needs attention.
Noticed 80% of fractionals take a full-time gig within a year?
Noticed freelancers offering 'slots' they have available for...well, anyone with cash wanting them to do anything at all? It's not honest, it's not autonomy in any sense; it's not what they're telling themselves and anyone who'll listen it is. They don't have slots available, they have bills to pay. There's not enough work to go round, and you have to be realllllllllly good, connected and lucky to not have months that are tough. And years.
And that's why I'm speaking out against the freelance = freedom lie. Because too often it's not a first step on a good journey, it's the rainy, ill-prepared for weekend in Snowdonia that puts you off ever trying to have an adventure again.
True freedom and purpose require us to go deeper. We need to dismantle the old patterns and assumptions that have tied us to the corporate world in the first place. We need to be a little more honest.
The Illusion of Freedom in Freelancing
Freelancing within a broken, morally ambiguous, economically unstable system doesn’t offer true freedom.
Freelancing can look a lot like corporate life, just with fewer benefits and less security.
When we leave the corporate world only to freelance for the same clients, within the same industries, we’re essentially saying: I want to keep using my skills in the same ways, in pursuit of the same goals, and working with the same sort of people.
And if you can say that, and your there's no conflict between your values and the ends to which your work is put, and you genuinely are living the best version of you, I curtsey to you and invite you to write an article and tell us all how it's done.
Many freelancers quickly find themselves locked into a cycle of endless pitching, competing for contracts, constantly proving their worth, chasing unpaid invoices and dealing with clients who treat them as on-call, replaceable and last of the priorities.
Add to that, we're now in a culture which is icreasingly see people declare their politics on LinkedIn both as a heartfelt and inevitable response to injustice and - let's be honest with each other here on Unplugged Ambition - as a kind of signalling, tribalism and attempt to win kudos.
when we freelance, we remain deeply dependent on a system that operates according to values feel conflicted about. But now we have less power. And speaking out about anything becomes riskier. No one has your back. You have no idea where next month's rent is coming from. Another freelancer will alwaus do it faster, for less, or without the attitude.
It's a race to the bottom dears, not an aspiration.
Freelancing as a Delusion: Facing the Fear of True Change
The idea that freelancing is the path to autonomy is a delusion born from fear. It’s the kind of thinking we turn to when we feel exhausted and lost, and instead of asking, “What do I really want?” we cling to an option that seems 'allowed', and which we see role-modelled and which seems rapidly achievable.
Freelancing feels like a brave move on the surface, it feels like a change because it sounds like a change, but it's sticking a new label on an old jam jar and expecting the jam to be different.
It's motivated often by trivialities: avoiding the commute, enjoying a lie in, dropping the kids (who are old enough to get the bus) at school, not having to work with dev teams.
Or it's motivated by a reluctance to own and embrace failure.
I'm sure you've seen those folks...the ones made redundant from your org, who hit you up for ay contacts you had, then wore the Open to Work badge for six months, then excitedly announced on LinkedIn that
I get it. But is this drive coming from a sense of purpose, a realistic prospect of economic success...or a personalisation of the shame of being unemployed
but without a clear purpose, it’s simply a way to avoid the scarier reality of redefining who we are.
Often, the impulse to freelance stems from a subtle form of Stockholm Syndrome. We’re so steeped in corporate values, in seeing ourselves as our job titles and KPIs, that we think we’re nothing beyond our current skill set. We forget that our value doesn’t come from our resumes or our deliverables; it comes from who we are outside these structures. But when we don’t know how to start discovering that, we default to freelance work, hoping we can escape the system while secretly staying dependent on it.
This is not freedom. This is a symptom of not being well.
Freelancing Won’t Fulfill Your Deeper Needs
How did you get here?
Were you made redundant...left with feelings of failure and rejection, to hastily rebuild a life that had been orientated around the salary and status of corporate life? Is freelancing your face-saving fallback option you'd abandon at the first opportunity? Are you in the denial stage of growth?
Go easy on yourself.
Were you burned out...one too many bad bosses and bullshit loyalty tests? Is freelancing your big brave fuck you to a world who wishes you had the balls to bring your authentic self out to the pitch.
Go easy on yourself.
When we step into freelancing without a greater sense of purpose, we often find ourselves re-creating the very dynamics we were trying to escape. Many freelancers end up with worse financial security,greater unpredictably as to their week, and a lingering feeling that they’re still just “working for the man,” just with a different email signature and, er, a logo you bought on Fiverr.
Freelancing doesn’t ask us to rethink the way we work, only where we work. But if we’re truly ready for a radical change, we need to go beyond these surface-level adjustments and ask ourselves: What would I be doing if I didn’t feel beholden to the skills that corporate life taught me?
Real Freedom: The Courage to Go Beyond
Choosing an alternative path means breaking free of the belief that we’re only as valuable as our corporate skills. True freedom is the courage to undergo a real learning journey, the kind that may take you far beyond the familiar limits of your current expertise. It’s a path that might lead you to ask different questions, build connections outside your usual circles, and discover talents and values that were hidden under years of corporate conditioning.
This takes time. I'm always straight with you guys: this 'journey' from corporate clone to alternative entrepreneur, to being a person you actually like, and like being, and are proud of, takes three to four years.
We're working desperately hard to build pathways, programmes, community and resources that might reduce that to say 2-2.5 years. We've already got a bunch of resources and 12 focus areas that require your attention.
But there's work involved: self-awareness, learning to learn, building new sustaining relationships, redefining your relationship with money, healing from toxic workplaces, understanding the likely future of work in a technology-driven world.
I think what you like about the idea of going freelance is...it's so damn quick. Spin up a wordpress site, make an announcement on social media...you've done it. And all without ever having to face a lot of uncomfortable truths.
Unplugged Ambition, and coaches and other programmes, help professionals unravel these corporate beliefs and build a life around their values, not just their skillset. Joining a group of like-minded individuals who are also shedding the expectations and limitations of traditional work allows you to go deeper than freelancing alone ever could.
Or consider working with a coach who can help you craft a vision that goes beyond just finding a few clients; they can help you set objectives that align with who you want to become, not just what you want to do.
Freelancing Can Be the First Step, but Don’t Let It Be the Last
Freelancing isn't a wrong or a bad choice. It can be a valuable stepping stone in your journey if you use it as a launching pad, not a destination.
But if you’re dreaming of liberation, remember that freedom isn’t the absence of a 9-to-5 or being able to go the gym in your lunch hour. Freedom is the courage to break away from the systems that tell us we’re only worth what we can produce, and the audacity to craft a life based on purpose and authenticity, even if that life looks entirely different from the one you’ve been told to pursue. Eve if your Aunt Susan tells people you're still Head of Customer Success because she's embarrassed you make artisan jams and sell them in the farmers markets of Umbria with your bad Italian accent.
What I'm saying is, Fuck Aunt Susan.
Working the same jobs for the same companies under a freelance banner isn't alternative entrepreneurialism. It's a poor route to happiness from the many freelancers who are honest with me about the constant pitching, the constant pressure on pricing, the Groundhog-day like way of working which seems them having the same tell-me-like-I'm-five-years-old
True freedom isn’t found by staying comfortable; it’s found by being brave.