Case Study
Retirement planning for a successful business owner
Nearly a decade ago, Denise – a successful entrepreneur and business owner – began working with Jon Orchard at Old Mill. While she had no immediate plans to retire, she had started to consider stepping back from her business within the next ten years. Her primary objective was clarity: to understand when she could realistically retire, how much she could afford to spend, and what kind of lifestyle her wealth could sustain after leaving the business.
From the very beginning, the conversation wasn’t just about products or investment returns. It was about purpose. Jon’s approach centred on lifestyle financial planning — helping Denise articulate a clear vision for life after work and building a financial strategy to support it. The goal was peace of mind, not just performance.

29th April 2025
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Jonathan Orchard See profile
The process began with the creation of a comprehensive long-term cash flow forecast – a cornerstone of Denise’s ‘Personal Financial Plan’. This living plan provided the strategic foundation for both her personal and business decisions in the years that followed. It confirmed that retirement within her ten-year horizon was achievable, assuming a few key financial levers were optimised.
- With the business performing well, Jon and the team focused on enhancing tax efficiency and extracting capital in a way that protected Denise’s long-term wealth.
- Significant pension contributions were made to take advantage of available tax reliefs.
- Existing pensions were reviewed, consolidated, and moved into a more suitable investment structure.
- Accessible investment portfolios were created alongside pensions to provide flexibility – ensuring funds were available should Denise choose to retire earlier than expected.
- Tax allowances were fully utilised each year, gradually building a diverse, tax efficient portfolio designed to support income needs in retirement.
- As Denise’s retirement plans became more concrete, the financial plan was regularly updated and rigorously stress tested – including modelling the effects of a market downturn at the point of retirement. This provided the reassurance she needed to move forward with confidence, regardless of market conditions.
Following the eventual sale of her business, Jon helped design a structured plan for the proceeds.
- A cash portfolio was established to provide immediate liquidity and stability.
- The balance was invested into longer-term, tax efficient structures, aligned with her income needs and investment preferences.
- Initially, income was drawn from cash reserves – allowing her invested capital to grow undisturbed during periods of market volatility.
Today, Denise is fully retired and financially secure. Through thoughtful planning and disciplined execution, she now has the freedom to enjoy life on her terms – with absolute clarity around her finances and no pressure to return to work.
Her personal financial plan remains a central tool, providing structure and guidance through life’s inevitable twists and turns. With a robust strategy in place and a trusted advisory team on hand, Denise can confidently focus on what matters most in this next chapter – knowing her financial future is both resilient and aligned with her lifestyle goals.
“Working with Jon and the team gave me the clarity and confidence I needed to step away from my business and into retirement. Having a clear plan meant I could make decisions without fear, knowing my future was secure. It’s given me the freedom to enjoy life without worrying about finances.” – Denise