Summary of Mistakes Were Made

Overview of ChooseFI — “Mistakes Were Made”

This roundtable episode features Brad Barrett with Katie and Alan Donegan reflecting on major financial and life mistakes they’ve made, and what those mistakes taught them about investing, confidence, communication, and building a life on their own terms. The core message: you do not need a perfect path to reach financial independence, and many of the best lessons come from expensive errors—especially when you learn from them and keep moving forward.

Key Themes and Takeaways

• Mistakes are normal, not exceptional

  • Everyone makes them, including people who are financially independent.
  • The important part is learning quickly and not letting one bad experience define your future.

• Index investing beats speculation

  • Several of the worst mistakes discussed came from trying to get fancy with stock picks, actively managed funds, and speculative real estate.
  • The episode repeatedly reinforces that boring, low-cost index funds are the simplest and most reliable long-term path.

• Confidence matters as much as net worth

  • Fear, comparison, and people-pleasing can cost money and limit freedom.
  • Building confidence can improve career decisions, negotiations, relationships, and business growth.

• Financial independence creates optionality

  • Having “FU money” or even just more breathing room makes it easier to speak honestly, set boundaries, and make decisions based on values rather than fear.

Biggest Financial Mistakes Discussed

Alan’s investing mistakes

• Went all-in on a high-tech managed fund before the dot-com crash

  • Invested about £7,000 of life savings into a tech-heavy active fund.
  • It collapsed to under £1,000.
  • The real mistake, Alan says, was not the loss itself—it was being scared out of investing for 13 years afterward.

• Misunderstood the stock market

  • He assumed the market was inherently dangerous and gravitated toward property instead.
  • Later learned the difference between stock picking, sector bets, and simple index fund investing.

Brad’s early investing mistakes

• Bought company-recommended stock picks as a student/intern

  • Invested in top-pick stocks from a major firm; both went bankrupt.
  • Reinforced the idea that “expert picks” are often just sales pitches.

• Paid high-fee mutual fund loads

  • Was sold an expensive fund with large upfront and ongoing fees.
  • Learned that hidden fees can quietly destroy returns over time.

Katie’s investing mistake

• Trusted a random financial advisor who called her at work
  • Was sold actively managed funds with very high fees:
    • 3% entry charge
    • 2.71% ongoing fee structure
  • Initially accepted the advice because she lacked experience and didn’t know what fees were reasonable.
  • The couple estimates this choice could have cost them around £1 million / $1.3 million in long-term wealth.

Brad’s speculative real estate mistake

• Bought speculative golf-course land in North Carolina
  • Used interest-only loans with balloon payments.
  • The purchases were driven by hype and “greater fool” speculation.
  • The market later collapsed, leaving him paying the properties for years.
  • The stress lasted more than a decade and likely cost over seven figures in opportunity cost.

Brad’s speculative fund mistake

• Bought into the Cathie Wood ARK investing craze
  • Later admitted he ignored his own advice and got swept up in narrative-driven speculation.
  • The lesson: when everyone is excited, it’s often already too late.

Life Mistakes and Personal Growth Lessons

Alan’s “write a book on the work laptop” mistake

• Wrote a critical book about bad business practices using his employer’s laptop.
• Got caught and fired, then had the firing unwound and was paid to leave.
• The deeper lesson:
  • He should have spoken directly to the boss.
  • He also learned not to use work resources for personal projects.

Alan’s honesty/avoidance mistake

• Lied to avoid a social interaction instead of saying no directly.
• The lie damaged a friendship.
• Takeaway: honest no’s are usually better than polite lies.

Katie’s comparison and confidence issues

• As a child, she compared herself against peers to determine self-worth.
• Felt good in netball because she ranked well locally, but less confident in football because she was surrounded by stronger players.
• The same pattern showed up in school and university: being a “big fish in a small pond” didn’t prepare her for environments where everyone is talented.
• Main lesson: confidence based on comparison is fragile; confidence needs to come from inside.

Katie’s “studies over everything” decision

• A coach encouraged her to continue pursuing netball seriously.
• She immediately declined because she believed academics had to take priority.
• The reflection wasn’t “I ruined everything,” but rather:
  • life is full of alternate paths,
  • you don’t always need to choose one identity over another,
  • and being open to multiple paths can be liberating.

Business and Career Lessons

Build your own audience

• Alan regrets not building an email list while growing his business.
• Social platforms are fragile and controlled by outside companies.
• Email remains the most reliable way to communicate with your audience.

Don’t outsource your business to platforms you don’t control

• The episode warns against relying on Facebook, Twitter/X, Amazon, or other platforms that can change rules, algorithms, and fees at any time.
• Build direct relationships with customers, readers, or community members.

Don’t ignore salary negotiation

• Brad admitted he under-negotiated a job move because he lacked confidence and the right language.
• Better scripts and more confidence would have improved the outcome significantly.

Notable Insights

• “The wisest thing you can do is learn from other people’s mistakes.”
• “Spend as much time building your confidence as you do your net worth.”
• “You are more free when you have financial independence.”
• “Try” usually means no. It’s often better to say no clearly.
• People choose suppliers because they are fun to work with as much as because of price or quality.

Action Items / Practical Advice

• Keep investing simple:
  • Prefer low-cost index funds over stock picking or speculative funds.
• Watch for hidden fees:
  • Even small percentage differences can cost millions over time.
• Build an email list if you run a business:
  • Don’t rely on social platforms as your only audience channel.
• Practice saying no clearly:
  • Honesty and boundaries prevent confusion and resentment.
• Work on confidence:
  • Especially around salary negotiation, speaking up, and comparison.
• Learn from mistakes faster:
  • Make them, reflect, adjust, and keep going.

Final Takeaway

The episode is a reminder that financial independence is not the result of a flawless track record. It’s the result of learning, adapting, and avoiding repeated expensive errors. Brad, Katie, and Alan show that you can make huge mistakes—bad investments, bad business choices, bad communication habits—and still end up building a rich, flexible, and meaningful life.