What I Would Tell My Younger Self About Careers and Running a Business

If I could sit down with my younger self today, I wouldn’t start with advice.

I’d probably start by listening — to the ambition, the urgency, the desire to move fast, and the quiet fear of falling behind.

Back then, everything felt like it needed to happen quickly. Career progression. Titles. Income. Recognition. Certainty.

What I didn’t realise then was how much of life and business is shaped not by speed — but by judgment.

On Career Choices: Progress Isn’t Always Upward

When you’re younger, it’s easy to believe that a good career is a straight line.

Better role. Better title. Better pay. Repeat.

What experience eventually teaches you is that some of the most important career moves don’t look like progress at the time.

They look like:

• lateral shifts

• uncomfortable learning curves

• roles that stretch you but don’t impress others

• periods where you gain perspective, not status

I would tell my younger self this: Don’t optimise only for momentum. Optimise for learning and judgment.

Titles fade. Skills age. But how you think compounds.

On Corporate Life: Learn the System Before You Try to Escape It

It’s fashionable to dismiss corporate life once you start a business.

But looking back, I’m grateful for my years there.

Corporate environments taught me:

• how decisions are made at scale

• how stakeholders think

• how risk is managed

• how structure creates stability

• how governance protects longevity

If I had skipped that phase, I would have lacked the perspective to see what actually breaks when businesses grow.

I’d tell my younger self: Learn how the system works before you decide it doesn’t suit you.

You don’t have to stay forever — but understanding it deeply is an advantage.

On Starting a Business: Freedom Comes With Weight

Running your own business is often described as freedom.

And in many ways, it is.

But what’s rarely talked about is the weight that comes with it.

Cash flow stops being theoretical. Decisions follow you home. Mistakes feel personal. There’s no one else to escalate to.

I would tell my younger self this: You don’t just gain freedom when you run a business — you inherit responsibility.

If you’re not prepared for that trade-off, the freedom won’t feel freeing at all.

On Cash Flow: Respect It Early

No spreadsheet, forecast, or business plan truly prepares you for the emotional reality of cash flow.

When you’re responsible for payroll, commitments, and timing, money becomes more than numbers.

It becomes judgment.

I learned this the hard way — and I’d tell my younger self to learn it earlier: Cash flow discipline isn’t conservative thinking. It’s survival thinking.

Growth without cash discipline is fragile. And fragility eventually shows up.

On Decision-Making: This Is the Real Skill

If there’s one thing I’d emphasise above all else, it’s this:

Careers and businesses don’t break because of a lack of ideas. They break because of poor decisions made under pressure.

The most valuable skill I’ve developed over time isn’t execution. It’s learning how to think clearly when:

• information is incomplete

• stakes are high

• time is limited

• emotions are involved

That skill wasn’t taught in school. And it wasn’t taught early in my career.

I wish I had invested in developing it sooner.

On Seeking Help: It’s Not Weakness, It’s Maturity

When you’re younger, asking for help can feel like an admission of inadequacy.

Later, you realise it’s often the opposite.

The people who progress most sustainably are those who:

• seek perspective

• test their thinking

• talk things through

• recognise their blind spots

If I could tell my younger self one final thing, it would be this: You don’t have to figure everything out alone.

At certain stages of life and business, thinking with someone else isn’t optional — it’s essential.

A Closing Thought

If you’re earlier in your career, you don’t need to have everything figured out.

And if you’re already running a business, you’re not behind for still having questions.

Both paths are complex. Both require judgment. Both benefit from reflection.

If there’s one thing I’ve learned, it’s that clarity doesn’t come from rushing forward.

It comes from understanding yourself, the environment you’re operating in, and the trade-offs you’re willing to make.

That’s what I’d tell my younger self.

And that’s what I try to practise now.