Clients can be doing perfectly well. Their portfolios are growing, returns are steady, and the long-term plan is intact. Yet, like scrolling through Instagram, they begin to feel left behind. Everyone else seems to be living larger, travelling farther, dining like royalty, and investing smarter. Friends boast about “killer stocks” or “unbelievable returns”, and suddenly the steady growth in their own portfolio feels inadequate.
This is what I call the Instagram Illusion. Comparing your reality with someone else’s post on Reels. In investments, it’s just as dangerous as in life. Clients start chasing the mirage, inviting new advisors who promise shortcuts, and abandoning the discipline that built their wealth in the first place. The irony is that most of these stories are exaggerated, cherry-picked, or simply lucky. But envy doesn’t care about truths — it cares about appearances. And appearances can be costly.
The Winner’s Tale bears a close resemblance to the Instagram illusion. It usually happens after a holiday or a weekend away. Clients return from the coast, a wedding or a dinner party, and suddenly their portfolios feel lacking. Why? Because everyone they spoke to seemed to have “bagged a winner”. A friend brags about a biotech stock that doubled, another about a mining venture that soared, and yet another about a stake in a private equity deal that sounds too good to be true.
The Winner’s Tale is the belief that everyone else is making smarter, faster money. The problem is that cocktail parties are breeding grounds for selective memory. People rarely mention the losers they backed, the funds that underperformed, or the risks they took to get those returns. They only talk about the winners. Clients, hearing only the highlights, begin to wonder: why doesn’t my portfolio manager own that stock? Why isn’t my portfolio producing those returns?
The danger is obvious. Chasing other people’s tales of riches leads to impulsive decisions, unnecessary risk, and a portfolio built on envy rather than discipline. The truth is, most of those “winners” are either inflated or unsustainable. But in the glow of a cocktail party they sound irresistible. And that’s when rational investing gets left in the pub.
Death by tax obsession
Few topics stir more emotion than death. Clients spend an extraordinary amount of time and energy trying to outwit the taxman from beyond the grave. They set up trusts, structures and elaborate estate plans, convinced that the ultimate victory is leaving their heirs a tax-reduced fortune.
This is the Legacy Labyrinth. Living to die. The irony is that once the tax structures are in place, the obsession doesn’t end; it deepens. I often tell clients, half in jest: “Now I suppose you can die.” But the reality is, heirs rarely care about the tax mechanics. They don’t pore over estate structures or marvel at clever planning. They care about one thing: the money.
The tragedy is that in the pursuit of minimising death taxes, many clients forget to enjoy life. They sacrifice experiences, delay spending, and live in fear of the inevitable. The lesson is simple: tax structures are important, but they are not life. Wealth is meant to be lived, not hoarded in anticipation of death.
There’s a curious bias among investors: if something is simple, it can’t possibly be good. A straightforward proposal — clear, transparent, easy to understand — is often dismissed as “too basic”. Instead, clients swoon over alternative asset funds, structured products with guarantees, fund-of-funds and exotic emerging-market vehicles. The more obscure the investment, the more sophisticated it must be.
This is the Complexity Fog. Mistaking opacity for quality. Clients convince themselves that complexity equals superiority, even when they don’t fully understand what they own or how it performs. The absurdity is that the most reliable investments are often the simplest. Businesses with strong fundamentals, steady cash flows and transparent reporting. But simplicity rarely dazzles. Complexity, on the other hand, creates the pretext of brilliance.
The danger is obvious. When investors wander into a fog of complexity, they risk ending up with portfolios they can’t explain, products they can’t evaluate and outcomes they can’t control. The fog feels mysterious, but it’s still fog — murky, disorientating and, ultimately, empty.
Over-feathering your nest
For many clients, a home is more than shelter. It’s the ultimate comfort symbol: the warm, reassuring nest. The story they tell themselves is that this nest doubles as an investment, a safety net for retirement, a fortress of security.
This is The Fable of the Nest Egg: the comforting tale that owning a home is both a lifestyle and portfolio cornerstone. In reality, a house is one of the most expensive assets you’ll ever own. Repairs, repainting, replacements. The expenses never stop. The roof leaks, the plumbing breaks, the walls need fresh paint and the garden demands attention.
In fact the only time it truly becomes an “investment” is when the children ship you off to an old-age home, sell the house and pocket the proceeds. Until then, it’s not a wealth generator. It’s a consumption item dressed up as an asset.
So don’t confuse lifestyle with investment. A home provides shelter, comfort and identity, but it rarely delivers the returns clients imagine.
Markets rise and fall, companies succeed and fail, but the hardest part of investing has nothing to do with numbers. It has everything to do with human behaviour. The Instagram Illusion, the Winner’s Tale, the Legacy Labyrinth, the Complexity Fog, and the Fable of Nest Egg are not market forces — they are emotional forces. They push clients to compare, to envy, to overcomplicate, to obsess and to cling.
Investing is actually straightforward. Choose good companies, diversify, stay disciplined. What makes it hard is managing the emotions that constantly threaten to derail that discipline. The real work of wealth management isn’t just building portfolios; it’s guiding clients through the illusions, traps and mirages that come with money.
In the end, investing is easy. Behaviour is everything. Master the psychology, and only then will the numbers reveal the full story.
