“I Have Enough Money to Last Me the Rest of My Life… Unless I Buy Something.”

“I Have Enough Money to Last Me the Rest of My Life… Unless I Buy Something.”

— Jackie Mason

It’s a humorous line from the late comedian Jackie Mason, but for business owners approaching retirement, it cuts close to the bone.

When you're in control of a profitable business, it’s easy to feel financially secure. You have flexibility over income, dividends, and investment decisions. But once you retire, the equation flips.

You move from building wealth to drawing it down. And suddenly, every purchase—whether it’s a new car, a second property, or helping children financially—directly impacts how long your money will last.

What Does This Mean for Prospective Retirees?

Many directors underestimate what it takes to sustain their current lifestyle once the salary and dividends stop.

Retirement isn’t a straight line:

• The early years are often active—travel, leisure, and lifestyle spending.

• Later years may bring care costs or increased health needs.

• Inflation steadily erodes the purchasing power of your money over time.

Without proper planning, the pot you thought would last comfortably can deplete far faster than expected.

What Is a Comfortable Retirement?

According to the Pensions and Lifetime Savings Association (PLSA), a “comfortable” retirement for a single person means around £43,100 per year, and for a couple, £59,000 per year. This allows for regular holidays, a new car every five years, and generous food and leisure spending.

However, for many business owners accustomed to a six-figure lifestyle, a more realistic target might be £60,000 to £100,000 per year—adjusted over time for inflation and evolving needs.

So How Much Do You Need?

To fund a retirement income of around £60,000 per year (after tax), sustained over several decades, a pension pot of approximately £1.25 million is typically needed.

This can seem like a daunting number—but it becomes far more achievable when broken down into a consistent, long-term contribution strategy.

Key Considerations for Limited Company Directors

1. Time is your greatest asset
The earlier you start, the easier the journey. Small but consistent contributions over time are far more effective than trying to play catch-up in your 50s.

2. Maximise the tax efficiency
Company-paid pension contributions are usually fully deductible against corporation tax, and funds grow free of income tax, capital gains tax, and—if structured properly—inheritance tax.

3. Don’t treat your business as your pension
A future business sale can be a welcome bonus, but it shouldn’t be your entire plan. Deals fall through. Timing can be unpredictable. And liquidity can be limited.

4. Build flexibility into your plan
Your retirement won’t be linear. A good strategy allows for different spending levels across the decades, plus buffers for care, emergencies, or gifts to the next generation.

Final Thoughts

Jackie Mason’s quip might make you laugh—but the truth behind it is serious:

You may feel like you have enough now—but without a structured, tax-efficient plan to support the decades ahead, you could find your retirement vulnerable to lifestyle drift, inflation, or unexpected events.

At Caldwell Financial, we help limited company directors and high-net-worth families build tailored retirement strategies—turning business success into long-term financial independence with clarity, control, and confidence.

If you’re unsure whether your current pension strategy is robust enough for the life you want, it may be time for a conversation.