In this presentation — When Do I Sell? — I explore why selling is the hardest part of investing. We’ll look at the many reasons investors sell, the common pitfalls we’ve all fallen into, and then I’ll share the framework I use today. I support this with recent examples of stocks I’ve sold, and finish with a look at some of my current holdings and how I’m thinking about potential exit points.
1. Introduction
-
Selling is the hardest decision in investing.
-
Paper trading can’t capture the psychology.
-
Biases: anchoring to entry, waiting for breakeven, falling in love with a story.
-
My biggest past issue: cutting winners too soon.
-
Improved by using a framework + building skill at buying back in when I’ve sold too early.
-
It’s not about winning every hand. It’s about stacking probabilities. Fold when odds aren’t in your favour and wait for the better hand.
2. Reasons People Sell
(broad, neutral list — not judged, meant to spark recognition)
-
Technical breakdown
-
Falling through support or resistance levels.
-
Overbought / oversold indicators.
-
Moving average crossovers (general).
-
Breakdown of a clear trend.
-
-
Change in investment thesis
-
Fundamentals shift.
-
Earnings downgrades.
-
Significant earnings misses.
-
-
Portfolio reshaping
-
Selling weaker positions to fund higher conviction opportunities.
-
Rebalancing for risk control.
-
-
Market-driven selling
-
Fear of crashes, recessions, geopolitical shocks.
-
-
Personal reasons
-
Tax planning.
-
Liquidity needs.
-
-
Behavioural reasons
-
Chasing another idea.
-
Boredom / story fatigue.
-
Overconfidence in calling tops.
-
-
Profit-taking
-
Locking in gains.
-
“You never go broke taking a profit” — first heard this from Rene Rivkin as one of his rules. I’ve come to realise thinking like this cost me a lot of money as it often means cutting winners too soon.
-
Capitulation
-
Selling because you just can’t bear the pain anymore.
-
This last one, capitulation, is where we cross into pitfalls. When selling shifts from disciplined to emotional.
3. Pitfalls
-
Anchoring to entry price.
-
Waiting for breakeven.
-
Selling too soon (my biggest past issue) – happy with a quick profit.
-
Falling in love with a story/company.
-
Not admitting you’re wrong quickly (and refusing to buy back in).
4. My Framework
-
Multi-period analysis (monthly, weekly, daily alignment).
-
3EMA crossovers — my consistent technical signal.
-
Fundamental triggers:
-
Change in investment thesis (downgrades/misses).
-
Selling weaker positions to fund stronger conviction ideas.
-
-
Other indicators I’ve trialled but don’t rely on now:
-
ATR trailing stops.
-
% fall rules.
-
Dollar-loss limits (% of portfolio).
-
5. Case Studies – some recent sells
-
Trigger: Technical weakness led to sell and recent unexplained CEO change added risk.
-
Outcome: Now 17c, higher than my sell point.
-
Lesson: Rules kept me disciplined, but sometimes that costs upside. Could have bought back in but change in fundamental picture has kept me out.
-
Trigger: Technical signals rolled over and change in fundamentals (new acquisition).
-
Outcome: Now ~$10 lower than when I sold.
-
Lesson: Framework worked. Reinforces discipline. Recent change in fundamentals brings about more short-term risk.
-
Trigger: Purely Technical entry and exit.
-
Outcome: ~$1 lower today.
-
Lesson: Reinforces technical discipline and trust in the process.
Portfolio walk-through – when would I sell?
-
SRV → Sold, then re-entered lower.
6. Wrap-Up
Selling is the hardest decision. There are many reasons investors sell — some rational, others emotional traps. My journey has been about moving from cutting winners too early to developing a more disciplined framework. I’m now better at cutting losers, holding winners, and buying back in when I’ve sold too soon. In the end, it’s about consistency and discipline: stacking the odds like in poker, and living to play the next hand.
Over time, consistency and discipline beat emotion.
7. Group Discussion
Prompts:
-
What’s your biggest struggle with selling?
-
Do you recognise yourself in any of these reasons or pitfalls?
-
Do you set sell rules before you buy?
-
Do you buy back in if you think you’ve sold too early?
-
What’s been your best or worst sell?
-
Looking ahead: how do you plan to improve your selling discipline?
Disclaimer: This information is provided purely for educational purposes. It takes no account of an individual’s personal financial circumstances and hence can in no way constitute financial advice. The above data may be subject to errors or inconsistencies for which the author takes no liability. It is imperative that all investors do their own research or if they need advice, seek it from a qualified financial adviser.
Presentation: When Do I Sell?