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What successful retirees sell before they stop working

By Sam Instone, 15 Mar 26

Most retirement planning focuses on accumulation – but Sam Instone of AES says the more interesting question is what to let go of

Most retirement planning focuses on accumulation - but Sam Instone of AES says the more interesting question is what to let go of

Most retirement planning conversations focus on what clients need to accumulate. After twenty years working with international families, I’ve found the more interesting question is what they need to let go of.

The retirees who thrive aren’t those who hold onto the most. They’re those who’ve made deliberate decisions about what genuinely serves the life they want now. Not the life they were building towards. The one they’re actually living.

Here are five things worth examining with your clients before they retire, and a straightforward framework for making those decisions well.

The family home is often the biggest trap

A client of mine, a senior partner at a Dubai accountancy firm, owned a six-bedroom villa in a desirable neighbourhood. By the time he retired, upkeep, utilities, service charges, and maintenance were running at over $50,000 a year. He sold, bought a low-maintenance apartment, unlocked $2 million in equity, and cut his annual costs significantly. He stopped being a villa manager and started being a life manager.

The question worth putting to clients with large properties: does this genuinely enhance my lifestyle and finances, or does it mainly reflect my past? If the honest answer is the latter, a detailed cashflow analysis with sensible capital market assumptions will usually tell you what to do.

Financially supporting adult children has a real cost

I worked with a couple who delayed their retirement by three years to help a son purchase a property in the UK. They lost three years of travel, hobbies, and family time. The son could have leveraged a mortgage and built equity gradually. A sibling dispute over the arrangement added further strain.

Support given without clear boundaries can compromise financial freedom and, paradoxically, undermine the independence it was meant to build. The most useful thing advisers can do here is help clients think through the second-order effects before making a commitment.

Luxury hobbies need honest accounting

One client owned five classic cars. In retirement, they were costing him over $50,000 a year while he barely drove them. He kept his favourite, sold the rest, freed $1.5 million in capital, and cut $40,000 in annual costs. The joy came back once the burden was gone.

The pattern is consistent. Assets that were once symbols of success can quietly drain the time, money, and energy needed to enjoy retirement. They deserve the same scrutiny as any other investment.

The 90-day vehicle test

A couple I worked with had two luxury SUVs. They committed to living with one for 90 days. They barely noticed the difference. Selling the second freed capital for travel and reduced ongoing costs. It’s a simple test, but an effective one. If clients can’t remember why they kept the second vehicle at the end of the trial, they’ve answered their own question.

Letting go of a work identity is the hardest sell

A senior partner at an international law firm retired comfortably but found himself missing the title more than the work. Volunteering helped briefly. What genuinely worked was a consulting arrangement, what I’d call ICE: Independent Continue Earning. He stayed intellectually engaged, maintained an income, and controlled his own schedule. Once he stopped needing external validation, he found new passions and a clearer sense of purpose.

This isn’t something that shows up in a cashflow model, but it shapes retirement more than most financial decisions do.

What to tell your clients

The framework is simple. For any asset consuming significant money, time, or energy, ask three questions: does it genuinely serve the life I want now? What is it actually costing me, including time and opportunity cost? What becomes possible if I let it go?

The 90-day test applies broadly. Ask clients to live as if the asset is gone. If the feeling is relief, that’s the answer.

Retirement doesn’t have to mean deprivation. It means optimising for what actually matters to them. Every asset demands attention. Letting go of the right ones frees space for the things that don’t.

Watch the full analysis here:

Sam Instone is CEO of AES International, the only CEFEX-certified fiduciary firm across the Middle East, Asia, and Africa.

Capital at risk. Any examples used are for illustrative purposes only, and you may get less back than the figures shown. Any financial promotions are intended for information purposes only and do not constitute an offer to invest or provide personal financial advice or tax advice. We do not take any responsibility for third-party websites and content linked to from this channel. Issued on behalf of AES Middle East Insurance Broker LLC, registered with the Ministry of the Economy, licence 571368, commercial registration 75162, regulated by the UAE Central Bank, licence no. 189. This material is intended for Retail Clients within the UAE.

Tags: AES International | retirement planning

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