My Five Biggest Career Mistakes (and What I’d Do Differently)

Mistakes happen. Growth is optional. Choose growth.

A career isn’t built by getting everything right. It’s built by learning quickly, adjusting often, and realising that the behaviours that feel small in the moment can shape how people experience you for years.

Some of the mistakes below didn’t even feel like mistakes in the moment, they felt normal, harmless, or even justified. But small behaviours compound, and the things you overlook early in your career can come back to bite you later.

Looking back, these are the five mistakes that taught me the most. I share them not to criticise my younger self, but because they’re the kinds of lessons that help you grow faster, lead better, and show up as the person you want to be at work.

1. Being negative instead of lifting the energy around me

Early in my career, I didn’t realise how much my attitude affected the people around me. I thought I was being “realistic” or “honest,” but what others experienced was negativity.

And here’s the subtle part I completely missed:

Sometimes I actually agreed with the initiative, I was only pointing out potential pitfalls. But if you don’t first verbalise your support, all people hear is the criticism.

When you skip the “I’m aligned” part, you sound like you’re pushing against the idea, even when you’re not. It creates friction you never intended.

It’s absolutely okay, and necessary, to highlight risks or challenges. But the difference between being respected and being avoided is simple:

Show your support, then bring your concerns, and always pair them with solutions.

People follow those who stay constructive, calm, and forward‑looking. I learned that your energy is part of your professional reputation, and it compounds just like your skills do.

2. Treating HR like a therapist

This one took me a while to understand.

HR is there to protect the company, not to process every feeling you’re having about your role, your future, or your frustrations.

Sharing every doubt or moment of stagnation doesn’t help you. It can actually limit your options.

What HR does respond well to is:

• Solutions

• Proposals

• Clear thinking

• A plan for how you want to move forward

It’s not about hiding how you feel. It’s about communicating in a way that shows maturity, stability, and direction.

3. Not being prepared with alternatives when the numbers slipped

When results weren’t tracking to budget, part of me wanted to stay loyal to the strategy and avoid panicking. But leadership doesn’t want to hear “trust the plan” when they’re under pressure.

They want agility. They want options. They want to see you thinking ahead.

And here’s something I learned the hard way:

Your alternatives don’t even have to be perfect, they just have to exist. Sometimes the value is simply showing that you’ve thought ahead, explored possibilities, and are willing to test ideas.

Being prepared with options isn’t abandoning the plan; it’s demonstrating leadership. It shows you’re not rigid, you’re not defensive, and you’re not caught flat‑footed.

4. Proving a point instead of doing the work correctly

There were times when I disagreed with a methodology or process, and instead of simply doing it the right way and explaining why, I followed the flawed method exactly to show how broken it was.

It was immature. And it wasted everyone’s time.

You don’t need to “win” the argument. You don’t need to make a point by letting something fail.

Just do the work well. Then explain your reasoning clearly and respectfully.

People listen more when you’re focused on outcomes, not ego.

5. Forgetting that conferences are still work

I once had too big a night at a conference with friends and couldn’t make my booth duty the next morning. A colleague covered for me and I was lucky.

But it was a wake‑up call.

When you travel for work, you’re representing the company. People remember how you show up. One misstep can follow you longer than you expect.

Just like how you dress, how you behave becomes part of your professional brand. You want to be known for your reliability, not your late‑night stories.

What I’d Tell My Younger Self

Stay positive. Stay solutions‑focused. Communicate with intention. Protect your reputation. Be ready with options.

None of these mistakes ruined my career, but learning from them accelerated it. And if you’re early in your journey, avoiding even one of these can save you years of frustration.

Growth isn’t about perfection. It’s about awareness. And awareness creates freedom.

Next Step: Bring This Into Your Five‑Week Calendar Review

Awareness only matters if you use it.

During your next Five‑Week Monday Review, look ahead at your upcoming meetings, projects, and interactions and ask yourself:

“Where do I have a chance of falling into one of these traps?”

• Is there a meeting where you might sound negative if you don’t express alignment first?

• A conversation with HR or leadership where you need to bring solutions, not frustrations?

• A performance discussion where you should prepare alternatives, even imperfect ones, instead of defending the plan?

• A process where you’re tempted to “prove a point” instead of just doing it correctly?

• A work trip or event where you need to be intentional about how you show up?

Flag these moments now. Name them. Then move forward with intention.

Small adjustments made early prevent bigger problems later and that’s the whole point of the Five‑Week Review. It gives you space to lead with clarity instead of reacting in the moment.