Becoming the Overseer of Your Investment Results
- Purple Lilac
- Dec 11, 2025
- 4 min read
By David Fagan

Most people spend their whole lives earning money and saving for retirement - but very few spend even an hour a year checking how well that money is actually working for them.
That gap between earning and overseeing is one of the biggest financial blind spots people have. Your investments might be the second-largest financial engine in your life - yet most people rarely check whether that engine is running properly.
This article is about fixing that. It’s about becoming the overseer of your own investment results.
Why People Avoid Checking Their Results
Whenever I ask someone how their investments have performed - a very
quantitative question - the answer usually starts the same way:
“I’m not sure, but…”
And then one of three familiar lines follows:
“My advisor is a great friend or relative.”
“I trust my advisor.”
“My advisor’s a really nice person.”
Trust is a wonderful thing.But trust becomes dangerous when it replaces oversight.
Trust feels good - but the results are your livelihood.
Being the overseer doesn’t mean managing your own money or picking your own investments. It means staying aware - knowing your numbers, asking direct questions, and understanding whether your returns line up with what the market is actually giving you.
Just like you wouldn’t hand your child over to someone and never check how they’re doing, you shouldn’t hand your financial future to someone and never check the results.
Oversight is not mistrust.
Oversight is care.
Client Story #1: The Cost of Blind Trust
Early in my career, I worked with a couple who had spent decades building a small business. They trusted a friend to manage their investments - someone they’d known for years.
After the financial crisis, their business was nearly wiped out. They sold what remained and barely made it into retirement.
When I reviewed their investment history, I discovered something alarming:Over the previous 15 years, their portfolio earned an average of 2.3% per year. Their advisor had them in segregated mutual funds.
If they had simply earned what the market offered - around 8% - they would have retired with roughly three times the amount they had.
That missing 5 or 6% wasn’t just numbers on a page.It was the difference between confidence and concern.Between a comfortable retirement and a fragile one.
And it wasn’t bad luck.It was a lack of oversight.
Client Story #2: The Cost of My Neglect
This one is harder to share because it was partly my mistake.
One of my long-time clients, a family doctor, saved $8,000 a month for 16 years. She started her career late, she worked incredibly hard, and she was the main provider for her large family.
One day, she sat across from me and said:
“David, I’m tired - I need to retire.”
When I reviewed her investment performance, I realized her portfolio had earned about 5% per year. If she had earned 8%, I could have told her she could retire that day.
That missing 3% - the quiet difference that compounds year after year - meant she needed to work another 6 or 7 years to secure the retirement she wanted for her family.
She did everything right.But she still didn’t reach her goals soon enough.And that wasn’t her failure - it was partly mine.
When I began working with her, I was only 28. I didn’t pay close enough attention to her returns. Later, I avoided the uncomfortable conversation with her broker because she was such a strong saver.
But I wasn’t doing my job as the overseer of her financial life.
That missing 3% represented something far more valuable than money - it represented time.Time she could have spent with her family, traveling, or simply resting after decades in a demanding career.
That’s the real cost of not overseeing.
How to Become the Overseer of Your Own Results
Becoming the overseer is easier than most people think.It requires awareness, not expertise.
Here are five simple steps:
1. Set clear goals.
Knowing what you’re investing for - retirement, freedom, helping your kids, or building a legacy - grounds every financial decision.
2. Review your actual results every six months.
This is crucial.
Ask yourself:“What was my return, and how does it compare to the market?”
You don’t need to understand every detail - just whether your results are keeping up with what the market is already offering.
3. Know your fees.
If you’re paying 2% or more, understand that even a 1% difference compounds into hundreds of thousands of dollars over time.
4. Ask direct questions.
Don’t accept vague answers like, “You’re doing fine.”
Instead ask:“How do my results compare to a balanced index portfolio?”
This isn’t confrontational - it’s responsible.
5. Stay curious.
You don’t need to be an expert.You just need to stay engaged enough to recognize whether your money is compounding the way it should.
Take One Step This Week - Here’s my challenge to you:
Take 15 minutes this week to check your investment return for the last 1, 3, and 5 years.Then compare it to a simple market benchmark.
That one small step can teach you more about your financial future than most people learn in a lifetime.
Oversight isn’t about spreadsheets or complexity -it’s about paying attention to the results that shape your life.
Trust feels good - but the results are your livelihood.



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