26 Aug 2026

Sailing to Retirement: Do you want a Flotilla or a Navy to ensure you reach your destination?

Work and life keep us all busy, even distracted. Smaller less important things can often fill our day, leaving us postponing the big, important questions. When I first helped Serena* (not her real name) she had just begun to think about retirement, but it is still a number of years away.

After a few decades of working for various different employers, and then more recently running her own business, Serena had an assortment of pensions scattered about. I often compare the journey to retirement to an ocean crossing. In Serena’s case, she had a ‘flotilla’ of small boats – each sailing with their own crew, and having only a vague sense of direction. There was no clear rationale to why she had chosen these particular boats and their contents (the underlying investments made in each pension).

Usually when people have legacy pensions they are remnants from previous employments. They may provide cheap custody, but also typically offer a limited selection of funds or portfolios to choose from. Not surprisingly, the funds available are most often operated by the same large firm that acts as the pension provider. So, while each of these little boats in a flotilla may appear cheap, they leave you to co-ordinate, and trying to keep track of what’s going on, and it can also be a hassle dealing with paperwork from several different providers.

I often find that a client may be better off making their pensions more strategically coherent: turning a flotilla into a navy that operates with a clear and unified purpose. This can include consolidating the small boats together into a single larger vessel – better able to sail the open ocean, and with the guidance and support of an experienced co-pilot like me.

Key advantages that can result from my advice include:

• strategic clarity and unified purpose in retirement planning
• cost efficiencies may be available
• a globally diversified, risk-appropriate investment strategy that is independent of the custodian holding the pension account
• better understanding of your personal retirement needs and what is required to make your desired retirement a reality

In Serena’s case, she had also put some money aside into a self-managed pension where she had chosen an assortment of rather exciting investments that had performed very well recently. Effectively, Serena now had a racing catamaran, alongside her various hobbycraft. A racing catamaran can be a lot of fun, but it also needs much more care, can capsize far more easily, and getting it back up can take a long time, and you hope you haven’t snapped the mast!

Without stretching the metaphor too badly, my concern for Serena, or anyone with a DIY portfolio like this has always been that the level of investment risk taken can be far greater than is first appreciated, and the downturn in value at that level of risk can be quite dramatic and potentially catastrophic as one gets closer to retirement. I’ve also encountered numerous stories of people making irreversible mistakes while managing their own pensions. My support, by contrast, will help Serena to avoid emotional reactions when stormy seas or treacherous reefs might be perceived to threaten her long-term goals.

If you’re an experienced sailor who has crossed several oceans, it can make sense to sail un-aided: personal stress and factors outside your control may be less likely to force you into bad decisions. But even for good sailors, especially because their own life is busy and distracting, it makes much more sense to have professional support with the bulk of your retirement savings that are intended to support your lifestyle well into the future. And, if you like, you can still also have a ‘fun’ pot of money to speculate with, but suffer no lasting harm if it plunges in value.

I have spoken in greater depth in a recent presenation about the journey to retirement and how this is much more than simply a financial decision – a good retirement plan should encompass body, mind, and meaning. Please get in touch if you’d like access to the full video. As a starting point, here’s a short snippet from that webinar regarding the value of professional advice in planning for your retirement: https://tinyurl.com/rk5x2mfp

How are you sailing toward your retirement destination? What support do you have to make it a successful journey?

Get in touch if you would like to have a chat or would like to set up a no-obligation conversation with me for someone you care about.

NOTE: The value of your investment can go down as well as up. Past performance is not a reliable indicator of future results. None of the above is financial or investment advice and you should speak to me or someone else professionally qualified to give you advice specifically tailored to your circumstances.