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Plan well for the future, while living well now

17 September 2026

Chris Kennedy has spent almost two decades advising some of the UK’s highest-earning professionals: partners at City law firms, barristers, and senior accountants. He’s spent his career helping people who are good at earning money to keep, grow, and eventually pass on their wealth.


A natural saver who grew up understanding the value of financial discipline, Chris, who’s based in London, helps clients find answers to the questions that matter most: how much is enough, when to stop working, and what ‘living well’ actually costs.


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Article last updated 17 September 2026.

Were you always careful with money, or did something teach you to be?

I think I was always a saver. It's just part of my character. My sister and I had quite different attitudes towards money, growing up. I was generally the one putting money aside rather than spending it straight away, so I developed saving habits fairly early.

There wasn't a single dramatic moment of realisation, but my father's influence was important. He often shared a lesson his father had passed down to him, “seven good years and seven bad years”. The principle was simple: when times are good, save, because they won't always stay that way.

Life has a habit of throwing up challenges when you least expect them, whether that's a change in circumstances, a period of uncertainty, or an unexpected expense. Having a financial cushion gives you choices and resilience when those moments arrive.

That's a lesson that has stayed with me throughout my life and career. It still shapes how I think about financial planning today.
 

Chris Kennedy | Financial Planning Area Lead, London

Having a financial cushion gives you choices and resilience.

Invest Well. Live Well.

Did the 2008 financial crisis change the way you thought about investing and planning well?

I started in the industry in 2006, so the financial crisis arrived very early in my career. It was impossible not to be affected by it. Across the financial services industry, many people were suddenly made redundant and faced significant uncertainty. It was a powerful reminder that circumstances can change far more quickly than most of us expect.

I also remember preparing a client review report early in my career, where a portfolio was around £1m lower than it had been six months earlier. Seeing that on paper was a powerful realisation. It brought home not only the scale of market volatility but also how difficult it can be for investors to remain calm and focused on their long-term plans during periods of uncertainty.

At the same time, it reinforced what I still believe is one of the most important principles of successful investing: don't let short-term market movements drive long-term decisions. In 2008 and 2009, many investors were understandably tempted to sell and move to cash. But those who did so risked turning a temporary decline in value into a permanent loss and missing the recovery that followed.

Over the course of my career, every major market setback has been accompanied by claims that "this time it's different". While each crisis has its own causes and characteristics, the lesson has remained remarkably consistent: markets can be unpredictable in the short term, but patience, discipline and a long-term perspective have repeatedly been rewarded.

 

How do you balance planning well for the future with living well now?

It's a genuine balancing act, and it's possible to get it wrong in either direction. I've always tried, both personally and with clients, to make full use of the available tax reliefs and allowances, whether that's higher-rate pension tax relief, salary sacrifice arrangements, or ISAs. Part of that is recognising that these opportunities may not always exist in their current form. More importantly, when you combine them with the power of compounding, taking action early can make a remarkable difference. Small, consistent decisions made over time often have a far greater impact than trying to make up ground later.

That said, I wouldn't subscribe to some of the more extreme interpretations of the FIRE movement (Financial Independence, Retire Early), where the objective is to stop working as early as possible. I’m wary because in some instances, this can mean sacrificing almost all current enjoyment. Life is inherently uncertain, and there’s a risk in postponing everything for the future.

For me, the right approach is somewhere in the middle. Financial discipline matters, but so does enjoying life along the way. The goal isn't deprivation; it's making thoughtful decisions consistently, so that you can build financial security for tomorrow while still making the most of today.
 

What does retiring well actually look like for your clients?

It's rarely a clean full stop. Many of the people I work with have spent decades building successful careers and reaching very senior positions. For them, stepping away isn't just a financial decision, it's a personal and psychological one. Some choose to gradually reduce their work commitments, while others prefer a more definitive break. Either way, the transition often takes time.

One of the biggest surprises is that the challenge of retirement is rarely the money itself. More often, it's adapting to a completely different relationship with money. During your career, income arrives regularly through salary, withdrawals from investments, or bonuses. In retirement, you're relying on assets you've spent years accumulating. That can feel uncomfortable at first, even when those assets are more than sufficient to support your lifestyle.

I regularly meet people whose financial plans show they can spend confidently and sustainably for decades to come, yet they're understandably cautious about making that shift. Part of our role is helping them understand where their income will come from, whether that's pensions, ISAs, investment portfolios or other assets, and giving them the confidence to enjoy the wealth they've worked so hard to build.

Ultimately, retiring well isn't simply about having enough money. It's about having the confidence and peace of mind to use it in ways that support the life you want to live.
 

What are the biggest financial decisions your clients face along the way, as they seek to live well before retirement?

For many of the people I work with, the biggest challenges aren't about whether they can afford something; it’s more about prioritisation when faced with competing goals. School fees, family experiences, helping children onto the property ladder, building retirement savings, and maintaining a lifestyle they enjoy today all vie for the same resources.

Education is often a good example. When I speak to clients who’ve paid for private education, it's not always a straightforward decision in hindsight. Some feel strongly that it was money well spent, while others question whether those resources could have been used differently. A common discussion is whether a significant sum spent on school fees might have a greater long-term impact if directed towards helping the next generation financially later in life.

There’s rarely a right or wrong answer. Good planning helps people understand the trade-offs and long-term implications of different choices. For example, taking advantage of allowances such as Junior ISAs and investing consistently over many years can create substantial opportunities through the power of compounding.

Ultimately, planning well often isn't about finding the perfect answer. It's about making informed decisions, understanding the compromises involved and ensuring your money aligns with what matters most to you and your family.
 

Chris Kennedy | Financial Planning Area Lead, London

Retiring well isn't simply about having enough money. It's about having the confidence and peace of mind to use it in ways that support the life you want to live.

Find out more

How does the conversation about planning well change as clients move into retirement?

The whole focus shifts. In the accumulation phase, the question is: do I have enough? Once that’s settled, it flips to: how do I not give too much to the taxman? Inheritance tax planning then becomes the dominant concern. It’s a fine balance – you can’t aim to have nothing left, because you don’t know when the end will come. It might be 75, it might be 100.

Care costs are part of that picture, but perhaps less alarming than people assume for higher spenders. The average care home stay is around four years, and around £60,000 to £90,000 a year. If you’ve been spending that in retirement anyway, as many of our clients have, it’s almost a continuation of your existing expenditure – just in a different setting.
 

What advice would you give your younger self about planning well financially?

Use the reliefs and allowances that exist, while they exist.  Don’t assume they’ll always be there. And start earlier than you think you need to – the compounding effect over time is genuinely extraordinary.

But don’t sacrifice the present entirely for the future.  Living well isn’t something that starts at retirement.  It’s something you should be able to do throughout your life – the holidays, the experiences, the things that matter to you and your family.  The goal isn’t to retire with the maximum possible pot.  It’s about looking back and feeling that you invested well in every sense of the word.

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