You Don’t Know How Much Money You’ll Need in Retirement — and That’s a Problem

For many business owners I speak to, especially those running creative agencies, the idea of retirement feels vague, far off, or simply overwhelming. When I ask, “How much do you think you’ll need in retirement?” the most common answer I get is simply:

“I don’t know.”

Some have tried to think about it but didn’t get far. Many haven’t really considered it because they’ve just been too busy building the business, focusing on revenue, and keeping things moving. The assumption is that retirement will sort itself out. Eventually.

But here’s the problem:

If you don’t know where the finish line is, you’ll never feel like you’ve arrived.

Why Business Owners Struggle with This

Unlike employees, business owners don’t have set salaries or employer pensions. They have to take ownership of their long-term financial security, and when everything is urgent, retirement takes a back seat.

The result? A subtle but persistent unease.

A quiet fear that you’re not doing enough… or maybe you’re doing too much.

Over time, that low-level anxiety builds. It becomes easy to ignore, but that doesn’t make it go away. It just becomes part of the background stress many founders carry with them.

What Happens When You Don’t Know Your Number

When you lack clarity on how much is “enough,” you can’t make confident decisions:

• You don’t know if you’re safe to slow down or sell.
• You may keep working long after you could have stepped back.
• You risk spending your 50s worrying about a problem that’s already solved, or worse, ignoring one that isn’t.

One of the most common questions I hear from clients in their 50s is:

“What do I need to do to be financially secure?”

Often, when we run the numbers and talk about their goals, they’re already okay. The money’s there, they just needed clarity. And that clarity often leads to one thing: relief.

Money Is Emotional

Once you can meet your day-to-day needs, money becomes more than just maths. It’s about time, freedom, identity, security and avoiding regret.

Creative professionals especially feel this tension. They take on difficult clients or projects they don’t enjoy because “what if…” There’s a fear of the famine, even when the feast is consistent. Not knowing your number keeps you locked in that mindset.

Knowing you have enough lets you say no to what drains you, and yes to what truly matters.

So, How Do We Figure It Out?

It’s both simple and complex.

We start by looking at your current lifestyle, what you spend, what you value, then we project that forward. What will still matter to you in retirement? What might cost more? What might go away?

Then, we model all of this using cashflow planning tools factoring in inflation, investment returns, business exit values, future spending patterns, and even later-life care.

What we get is a clear, flexible picture:

• Are you ahead? Great! maybe you can retire earlier or enjoy more now.
• On track? That brings peace of mind.
• A little behind? Let’s adjust course early enough to make a difference.

Retirement Is a Process, Not a Plan on a Page

We don’t just talk about numbers, we talk about you.

What does your ideal day look like in retirement? What would you regret never having done? Who do you want to spend time with? What kind of life are you working toward?

The process is conversational, iterative, and deeply personal. Often, people don’t have answers at the start, they discover them as we go.

The Real Goal: A Retirement Without Regret

The biggest risk isn’t running out of money.

It’s reaching your late retirement with plenty of money, but not the health, freedom, or clarity to enjoy it.

A successful retirement isn’t about numbers alone. It’s about freedom, purpose, and living a life that feels like yours.

If you’re not sure whether you’ve done enough, or just want to explore what’s possible, it might be time to start the conversation. If not now.. when?