The Milano–Cortina Winter Olympics started, and it reminded me of a decision I made seven years ago – a small bet with uncertain outcome. Optional upside investing for doctors is about making similar decisions with limited downside and asymmetric potential.
Back in 2019, I registered a domain linked to this exact event. No master plan, no guarantees. Just a small, deliberate action that could one day pay off. Seven years later, I’ll find out whether it was a minor loss or a surprisingly good investment.
Doctors and medics can apply the same principle to their financial planning. While you may not be buying domains, you can structure your portfolio so a few well-chosen positions have outsized potential, all while limiting the downside.
If you want a framework for building wealth and protecting what you’ve earned, check out Financial Protection for Doctors, which guides busy medics on how to prioritise income protection, life insurance, and critical illness cover before chasing growth.
Collecting Optional Upside: Lessons from My Domain Portfolio
Some people collect cars. Others collect watches. Some collect handbags. I collect domains.
Over the last decade, I’ve acquired 60+ domains:
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One paid back six figures.
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A few others did reasonably well.
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Most never had tangible financial value.
Some domains became real businesses, some useful tools, others are still “sleeping.”
That’s fine because I never saw them as guarantees. Each acquisition represented limited downside with potential upside – the essence of optional upside investing.
The lesson for doctors is clear: you don’t need every investment to be a home run. A few wins can make a significant difference if your risk is controlled.
Applying Optional Upside to Investing
You could even view index investing similarly. As of early 2026, the top 10 companies in the S&P 500 make up ~38% of the index, and the top 50 account for ~60%. Most of the gains come from a small number of winners.
Legendary risk thinker Nassim Taleb, author of Fooled by Randomness, describes situations where the downside is capped, but the upside is potentially unlimited.
Mohnish Pabrai, investor and author of The Dhandho Investor, summarises it simply:
“Heads I win, tails I don’t lose much.”
That’s a guiding principle for optional upside investing. You limit your losses, but position yourself where positive outcomes can disproportionately grow your wealth.
Real-World Examples of Optional Upside
Dharmesh Shah, co-founder of HubSpot, once bought chat.com for $15.5 million. He later sold it to OpenAI, reportedly in shares, giving him a stake in one of the most valuable private companies in the world. That wasn’t luck, it was positioning.
In finance, you can apply similar thinking:
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Small, low-cost, speculative bets in emerging sectors.
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Targeted exposure to high-growth companies within diversified portfolios.
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Structuring long-term investments in ways that protect principal while offering upside.
For busy doctors, automation makes this feasible. Using a system like AMASS — Automated Monthly Allocated Saving System lets you allocate capital systematically to both safe, predictable instruments and optional upside bets without constant monitoring.
Optional Upside and Career Assets
Optional upside investing isn’t limited to financial markets. Career moves, book projects, or side businesses can also generate asymmetric returns.
For example, I authored Moneywise Doctor, not for immediate royalties, but as a long-term credibility and business-building tool. The book became a trust-building asset, generating speaking opportunities, community engagement, and indirect income streams – all optional upside outcomes.
Doctors can leverage career projects similarly:
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Publishing guides, creating tools, or writing professional content.
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Developing a niche expertise that pays dividends over time.
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Making small investments of time or money with potential for larger future returns.
How to Start Making Optional Upside Bets
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Define your downside: Only commit capital you can afford to lose or risk. Optional upside only works when the negative is limited.
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Keep the upside optional: Position for large potential gains, but don’t rely on them for essential financial goals.
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Diversify: Just like my 60+ domains, not all bets will succeed. A few wins make the portfolio worthwhile.
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Automate: Systems like AMASS ensure regular contributions and optional upside allocations happen without decision fatigue.
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Think long term: Optional upside often takes time to materialise. Patience is part of the strategy.
Positioning Yourself for ‘Luck’
Sometimes, the smartest decisions don’t look smart at the time. They simply give the future a chance to surprise you.
Optional upside investing allows busy doctors to:
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Participate in high-reward opportunities.
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Maintain financial stability through structured protection.
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Benefit from asymmetric outcomes without taking unnecessary risk.
Your career and financial life both have optional upside opportunities. By combining deliberate protection, automated saving, and selective high-potential exposure, you position yourself where luck and timing can work in your favour.
Takeaway for Doctors
Optional upside investing isn’t about guarantees. It’s about:
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Limiting downside risk.
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Giving yourself exposure to rare but impactful wins.
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Leveraging systems and automation to make it feasible alongside a busy medical career.
Sometimes the most valuable decisions are the quiet ones you make years ahead. A small, deliberate bet today — whether financial, career-related, or personal can have a disproportionate impact on your future.
So, ask yourself: what small bet could you make today that may pay off years from now, without jeopardising what you already have?
Just Because Others Are Investing Doesn’t Mean You’re Ready
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