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The 5 Biggest Mistakes I've Made In My Career

I’ve made some good decisions in my career.

I’ve made my fair share of bad ones, too – some of them before I even had a full-time job.

These mistakes have made me conscientious, confident, pragmatic, and resilient – but I haven’t always viewed them this way.

It’s taken a year of deep self-reflection for me to be thankful for everything that’s happened to me, good and bad.

I’ve realised that the adverse moments and mistakes have brought out more in me and taught me more about myself than any of my successes.

However, in my younger years, I didn’t have this mindset. Not only was I oblivious, initially, to many of the mistakes I was making, but I also feared that they’d break me.

Here are the five biggest mistakes I’ve made in my career.

Table of contents

1. Not gaining more experience at a young age

I didn’t work in any capacity until I was two weeks away from turning 21 – and that was a three-day stint at the Southport Flower Show manning the gazebos.

My first regular job was at H&M, aged 22 (fresh out of university), and I didn’t have a full-time job until I was 23.

However, I’ll cut myself some slack and provide a wider context here.

There were a number of variables that thwarted my genuine intentions to get a job:

  • The worldwide recession from 2007 to 2009, which further diminished the availability of part-time jobs in Southport (which wasn’t exactly the epicentre of employment opportunities for teenagers who didn’t already have a job). At that point, it felt like unless you had concrete experience, nobody in the world would give you a job. But I go back to that age-old argument – how can you be expected to have experience if nobody takes a chance on you?

  • The fact I’d just moved from one part of the country to the other at the age of 17, didn’t know the area, and was more focused on making friends and regaining some sort of social stability.

  • My lack of serious willingness to get one.

I know what you might be thinking. How can I say I had genuine intentions to get a job but then say I wasn’t serious about getting one?

Well, it’s a bit like the film I, Daniel Blake. I did want to find work, but I wasn’t going to break my back to find it.

You see, I was extremely fortunate that I was the only child in a middle-class family, and money was never unattainable growing up. Not when it came to living a comfortable life, anyway.

Therefore, when I finished my A Levels, I spent three months not doing anything except waking up at 10 am every day, wandering aimlessly, and waiting for the weekend.

When I came home from university for the summer, I spent four months not doing anything except waking up at 11 am every day, reading books, and waiting for the weekend.

You might see this as an idyllic lifestyle. And you’d be wrong.

My life felt directionless. Purposeless. Hollow. I always felt I hadn’t ‘earnt’ my nights out, the Topman check shirt on my back, or the food I ate. (Here's a photo of me wearing said Topman shirt from 2010 to momentarily lighten the mood. Man, I miss that jawline. I'm also showing my age by posting a photo that was clearly taken on a digital camera.)

When I was around friends who had jobs and had established the value of earning money at a young age, I felt like the child in the room. A child in a room of children.

Looking back, I should have done more. At the very least, I should have volunteered to work for the local charity shop (which I eventually did in my early 20s), so that I understood and appreciated what a day’s work felt like. And I would’ve given something back to the local community.

I should’ve applied for more part-time jobs. Despite the scarcity of them, there were many I didn’t apply for simply because I had the mindset of ‘I don’t need to.’

I could’ve contacted local newspapers or marketing agencies in Liverpool and Manchester asking if they needed an intern for the summer (I didn’t know exactly what I wanted to do when I was 17 or 18, but I knew it would be something in marketing or journalism). I’m not certain any would have said yes, but I’m pretty confident one or two would have if I’d persisted over several years.

Aside from the fact it stopped me from learning about the value of money, this mistake also derailed my career before it even started. I was about two or three years behind people who gained work experience during university and subsequently worked in entry-level positions until I was 27.

It’s only in the last five years that I’ve managed to catch up – and I have no doubt that getting that work experience early on would’ve changed my career trajectory for the better.

2. Not fighting my corner

I could frame this as an overall life mistake rather than just a mistake limited to my career, but let’s keep it professional for the purpose of this article.

As with the previous example, I actually made this mistake before I even had what I would consider a ‘career’. It was when I was training to be a journalist, at the very start of my career.

One of the tutors was super aggressive. I mean, he could be a real Grade-A prick. I think he was compensating for something when he stepped through the door to the building because he seemed rather timid in external social situations.

He frequently chastised people in front of their peers, sometimes in a room of 30 to 40. He made some really below-the-belt remarks if you didn’t understand his instructions or did something he didn’t like. He was sarcastic when angry. He’d send emails highlighting individual mistakes, with your name in bold letters. He addressed me in this way once, and I didn’t respond or ever address it with him, which I regret.

To give him his credit, I learnt some valuable tips from him. He dished out praise when he felt you merited it, and he was forthright in his communication. There was no ambiguity – you always knew when you’d screwed up!

But his management philosophy (which I later replicated) seemed predicated upon the idea that you manage the situation, not the person – and I know that demoralised many people.

He’s one person I’d tell to fuck off now, perhaps in slightly less profane words. Perhaps.

I could cite countless other examples throughout the last ten years, but here are a few worth highlighting.

My first job in journalism

There’s a hilarious irony to my first-ever full-time job offer (I find it hilarious, anyway). I was offered a reporter job at the Bolton News on the condition that I passed my driving test and had my own car within three months.

So, I suppose even if I'd turned out to be the world’s best journalist, I would’ve been let go on the basis that I didn’t have a car. That theory makes sense. After all, this was Newsquest, and the company had frozen pay rises for five years, so it wasn’t going to continue reimbursing me for £2 bus tickets or £6 taxi fares.

The minions, of which I was one, had to park a ten-minute walk from the office because the staff car park was reserved for sales staff and one or two editors, yet the reason they gave for needing a car so soon after being offered the job was ‘so you can get to jobs quicker’. In some instances, it took less time for me to get the bus, or even walk.

Anyway, what’s ironic is a conversation I had with my then-editor two days into the role.

I needed to take time off work to continue my driving lessons (because, contrary to whatever ideas my editors had in their head, driving instructors don’t tend to work at 8 pm and all weekend), so I asked one of my editors if I could take the afternoon off a couple of weeks in advance. I was told, in no uncertain terms, that this wouldn’t happen and that “The fact you’ve not passed your driving test isn’t our fault.”

Had this happened now, I’d have asked her how she felt I could pass my test if I couldn’t have time off during the week and my instructor (who I’d built a rapport with for just under a year) didn’t work weekends. I’d have asked for her proposed plan of action and watched the cogs rigorously turn in her brain as they often did whenever someone dared to demonstrate free thinking.

Back then, though, I didn’t feel as though I could.

I could write another two thousand words on the smart alec peers I worked with (some of whom I told where to go, which I was proud of myself for), the dreadful working conditions I didn’t speak up about, and how I was backed into a corner when I left my job.

But what I’ve written here will suffice.

My time in PR

This article is becoming a rigorous test of my ability to say more with less. I'm not sure which traumatic experiences from my two-year PR career to highlight and which to leave out, as there are that many.

I’m going to be more abstract in the interest of not going off-piste and retaining my composure while writing.

There were several aspects of Public Relations that I wasn’t cut out for. I was cut out for some, but not for others. And the parts that I wasn’t cut out for, I really wasn’t cut out for – namely, admin-related activities.

However, I didn’t have to be told I wasn’t cut out for them in quite such a sadistic, backhanded, or agenda-driven way. And for all of my limitations, nobody ever asked me which areas I felt were my strong points or where I felt I offered the most value.

Believe it or not, I can think of at least ten unsavoury characters I met during my time in PR – and I only worked in the industry for two years and two months. They were unsavoury on the outside, anyway. I try to remember that everyone has internal struggles we don’t see, and these struggles manifest themselves in complex, often unpredictable ways. That said, I’ve never made someone cry in the middle of a meeting, as I once saw happen, so maybe I’m being too lenient.

I encountered people I thought were bullies, overt narcissists, people who deep down weren’t really that callous but felt they had to be in order to survive, and people who were at breaking point because of things going on in their personal life.

I had ‘conversations’ with these people I’d rather forget. I often replay these conversations numerous times in my head (which I know is only detrimental to me – I’m working on it). I imagine myself speaking to them in a completely different way from how I did at the time, which isn’t too difficult a concept to imagine given that I often didn’t say anything at all for fear of further reprisal.

Fortunately, from around 2017-18 onwards, I didn’t have many more of these conversations. I worked with mostly great people, and I’d found my niche in content marketing.

But the period from 2013 to 2017 had left its mark. When I became a manager, I wanted to set a different precedent – much like when someone becomes a parent and tries to eradicate the mistakes their parents made. This leads nicely to my next point.

3. Being too ‘pally’ with people when I became a manager

I wasn’t sure that I wanted to be a manager until about three or four years ago.

The idea of managing someone’s career development didn’t appeal to me – I still felt like I needed to develop in numerous areas before I could help someone else do the same. I also knew that such a role could entail a great deal of pressure, patience, and perseverance, depending on the type of personality I was managing.

But becoming a manager is just about the only way to gain a promotion (and a salary that reflects your expertise) in a lot of full-time in-house roles. A sad reality, but a reality nonetheless.

So, when I found out towards the end of 2019 that I was in line for a managerial role, I put my hang-ups to one side, and my initial reaction was one of optimism.

Not only did this promotion represent more responsibility, more authority, and better compensation, it was a golden opportunity to rectify the mistakes my managers had made.

What I never accounted for was the fact that I’m a human being and I was always going to make my own unique mistakes.

I didn’t manage the transition from being an executive to being a manager well. I thought I could be almost a carbon copy of myself, give out a few instructions here and there, and only ‘crack the whip’ when absolutely necessary.

I incorrectly saw management as dichotomic. I thought you were either:

  1. A manager who kept everyone at arm’s length, dished out a few ‘bollockings’ (as we say in the UK) to keep people on their toes, and exercised an almost Stalinist level of rule over your so-called subordinates.

  2. A manager who was a ‘friend first, boss second, entertainer third’ (to quote Ricky Gervais’ character David Brent from the UK (/superior) version of The Office.

However, my stint as a manager taught me three things:

  1. My theory was wrong. There are many more management styles than just two (the exact number varies depending on which article you read, but the general rule of thumb is seven. I’m not sure how you can condense billions of working human beings into seven categories, but who am I to argue with science?)

  2. Even the managers you think are Stalinist by nature are probably nothing like that outside of work. They’re just like that so that they don’t get caught out or exploited because, let’s face it – there are exploiters aplenty in the workplace. Speaking of which…

  3. Being a ‘friend first’ can seriously backfire on you if you’re managing people capable of abusing your laid-back nature. So, you shouldn’t be this type of manager unless you’re absolutely sure that you can revert to serious mode when you need to.

I learnt the first two lessons after my stint as a manager had ended, and I didn’t learn the third lesson until it was too late. Without referring to specific instances in this article, I'll say that I repeatedly found myself in a vulnerable position by trying to be 'one of the gang' or all things to all people.

My management style wasn’t as black and white as being everybody’s friend at all times – in fact, at times, I went too far in the opposite direction – but my willingness to be transparent and ‘real’ was more my undoing.

I walked a thin line over the space of two years, trying to be the person some of my managers weren’t. But I never fully appreciated the risks of my approach until it eventually blew up in my face.

I should have realised the distinction between being a manager and a peer, because there is a distinction – a big fucking distinction. And the people who nail this distinction without making any enemies are to be admired.

I can attribute my misfortune somewhat to covid, and the fact I was managing people from the front room of my house (which I barely left for two years except to go to the gym). I was in my head too often, and that caused me to make misjudgements and poor decisions.

In making this mistake, I empathised somewhat with my previous managers, because I realised how difficult a managerial role can be. Or, rather, how difficult it can be when you receive no fucking training whatsoever, which seems pertinent to most workplaces.

I asked. I was told, 'We're looking into it'. I asked again. I was told, 'We're still looking into it'. You get the idea. It never happened.

I learnt on the job. I had to suffer. But it moulded me as a person and showed me the path I don’t want to go down. So, as I said at the start – I have no regrets, even if, in a perfect world, things could've gone differently.

4. Being too aggressive at times

This was the other side of me as a manager. The Hyde to the Jekyll.

I don’t think I crossed the line too often, but when I was angry, people knew about it.

If I felt like my capability as a manager was being unduly questioned or threatened by the people I managed, or anybody for that matter, I lashed out. There’s no nice way to frame it.

You see, I didn’t want to be put in a vulnerable position like I was before I became a manager. And when I became a manager I got a bit high on my own self-importance.

I really wanted to put people in their place and remind them not to fuck with me again. I must have said ‘Have some of that, you cunt’ internally at least half a dozen times. To my mind, it was so easy not to annoy me, yet they’d somehow achieved that feat.

However – when I look back, I was too easy to piss off at times. Or rather, I showed that I was pissed off too much.

But that also doesn’t mean that the people I got pissed off with weren’t in the wrong in some way. They just weren’t as culpable for my frustration as I initially assumed. I have to take personal responsibility for the way I reacted because when I reacted that way, nobody won. And I definitely lost.

Before I said or did anything, I should’ve probed more. I should’ve asked someone why they felt the way they did or made the decisions they did or expressed the opinions they did. This not only would’ve put me in a position of control (‘adult mode’ as my therapist calls it), but it also would’ve allowed me to understand those people better, empathise with them more, and ultimately would’ve calmed tensions in the short and long term.

Instead, I was vulnerable (in ‘child mode’) and resorted to the easy action of wanting to get them back. In doing this, I showed myself in a bad light and misjudged people.

This part of my character was borne out of repressing my feelings for so many years, and I took all the anger that I’d bottled up out on the wrong people. Unfortunately, we all do that sometimes.

I would think that everyone above me in an organisation was out to get me and make my life difficult, and everyone below me was lazy and out to make my life difficult. Whichever way I looked at it, the world was out to get me – and I thought I had to show them who was boss. I’d say that theory was 90% paranoia. There was a modicum of truth to it.

Sometimes, in the aftermath of a tense situation, I took a mental step back, reflected, and feared that I was morphing into the managers I didn’t like much.

I often managed the situation rather than the person and I should have remembered that – shock horror – not everyone thinks like me. And this is a good thing – each of us needs to bring something new to the table.

Having undergone therapy for around eight to nine months, I've established some universal truths about life and people. Therefore, I think that if I were to work in a managerial role again, I could do it justice. As things stand, though, it seems unlikely that I ever will. And maybe that's a good thing.

5. Not believing in myself enough

Every single one of these mistakes comes down to this. It’s all about this. This is the biggest mistake I’ve made in my career and throughout my life.

I gave up applying for jobs because I didn’t think I’d get one. In truth, I didn’t think I deserved one. I thought I was a naive young layabout who couldn’t hack a proper job or provide value to a business. From the outside, I was nonchalant, bordering on arrogant about not having a job, but deep down I felt lesser than the people my age who worked.

I didn’t fight my corner when I was in my 20s because I didn’t think I could. I thought I’d struggle to get my words out if I tried to say my piece, or I might end up losing my composure and doing or saying something I’d regret. Therefore, the most appropriate course of action was to keep quiet and suck it up.

I frequently acted the same around my co-workers as I did around my friends because I didn’t trust myself to be professional without losing the essence of my character.

I was aggressive with people because I didn’t trust myself to manage difficult moments without resorting to anger.

In a nutshell, not believing in myself only caused problems in my professional life.

It also led me to experience what people call ‘imposter syndrome’.

I’ve lost count of how many times I’ve been in a meeting or presentation or worked on a project and thought, ‘I shouldn’t be here’ or ‘I’m not good enough to be doing this’.

On one particular occasion, I was doing a pitch for a pretty major client in the cookware industry – I really wanted to nail the presentation, and my slides were towards the end.

I’d slept about four or five hours the night before, even though I went to bed eight hours before I intended to wake up. I couldn’t eat anything the next morning. I sat down on my sofa, did some breathing exercises to calm down, and felt like I was on the verge of a panic attack. I almost closed down the lid of my laptop and went for a walk midway through the presentation because I was so nervous.

When it came to me, I’d breathed in through my nose and out through my mouth so many times (subtly, because I was on camera) that I was remarkably relaxed and nailed the presentation. But afterwards, I thought, ‘Why didn’t I think I was capable of this?’

Another prime example of not believing in myself at one point is – FourNine Marketing. I set this business up in June 2021 but did hardly any work on its behalf for the few months of its existence. I was too afraid to take the jump because I never thought anyone would want to work with me. I wasn't capable of running a business.

As I sit here now, one year into being a full-time freelancer, I can say that:

  • I am capable.

  • I am successful.

  • I’ve conquered so many of my inner demons.

  • I'm surrounded by pure people with a positive energy.

  • I’m determined to help impact people’s lives for the better.

I’m also aware that making mistakes is an innate part of the human experience. But being able to acknowledge some of my bigger mistakes, and share them with you, has been a massive catharsis for me. You have no idea.

I hope that, in some way, it has been for you, too.

Thank you for reading.


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