I went through a situation this tax season that reinforced a value I’ve slowly developed over the past half decade: an important lesson not to over-rely on others blindly. As an optimistic person, I see the best in others, and it has led me into several avoidable problems. As Peter Thiel stated in his interview with Joe Lonsdale this month:
“At the extreme, optimism and pessimism are the same thing. If you’re extremely pessimistic, there’s nothing you can do. If you’re extremely optimistic, there’s nothing you need to do. Both extreme optimism and extreme pessimism converge on laziness.”
I was lazy and suffered from inaction due to optimism because “there was nothing I needed to do.” I over-relied on others blindly.
I’ve learned to rely on the help of others but never to 100%. I historically went from being very independent, where I knew I could rely on myself and refused any help as I wanted to do everything myself, to the other extreme of 100% reliance.
How I Found Balance Between Two Extremes
Firstly, when I started Canadian Web Designs, I did everything — the websites, marketing, communications, the books, essentially everything top to bottom. After starting a team, I stepped into matters excessively and micromanaged, middle-manning everything. Then after COVID, I started going hands-off and placed a manager in charge whom I relied on 100%. Here lies the first mistake I made that cost me $20-50K depending on how you calculate wasteful spending, and a lot more if you factor in opportunity cost.
The person was good-willed but suffered from the same problem of being overly optimistic and trusted that everyone was doing everything properly without error. Without any checks in place, many holes formed in our systems with payments forgotten, clients neglected, and more fundamental problems arising. After the painful lesson of realizing I am ultimately accountable, I needed to establish my own checks and not rely on someone else entirely.
Implementing Checks and Balances
I set a few KPIs and measures for testing our systems and protocols. Here are some examples:
- Periodically, I pretend to be a customer and run through the website inbound lead process. I assess response times, how I am responded to, etc.
- I pick random clients and do a deep dive into conversations and billing to try and poke holes in our system to find breaks.
- I jump into meetings and ask questions to gauge the team’s understanding of a client or situation.
- One KPI is the number of Google reviews coming in.
Overall, this takes a few hours a month and serves as a method to check if the company is moving in the right direction and to catch issues early.
Leadership Evolution
An important change in leadership I implemented over the years is to not tolerate repetitive errors. What I tolerated, I would get, and I was overly accepting of errors. I still believe that with the right attitude, making mistakes faster means learning faster. It’s the repetition of the same or similar mistakes where I draw the line, as it shows an inability to learn — that’s what I have developed an intolerance for.
A Recent Example
Going back to my accountant, as she filed our HST and T2 this year, I had a quick calculation of what to expect in my head using QuickBooks. When the number was off by more than I expected, I investigated and discovered she had not inputted the data I had provided her. Furthermore, I caught her in a cover-up — essentially providing an excuse. Thanks to Grok, I discovered the audit logs in QuickBooks, and her statement did not match what the audit logs showed.
In the past, I would have relied on the accountant fully, without question, as I did not know QuickBooks and the tax system well enough. I’ve since learned it to avoid blindly relying on a third party. It’s foolish to assign a 100% probability that everything is done perfectly, despite hiring an expert. It’s foolish to be so optimistic that you believe there’s nothing you need to do regarding it.
The Balance I’ve Found Between Optimism and Pessimism
The balance I use now is to hope for the best but know that the true probability likely lies around 70-90%, depending on their expertise and skillset. Despite hoping for the best and expecting things will likely be done properly, I plan for the worst and have my own independent way of verifying.
Those who are more pessimistic might expect a different probability, perhaps 30-50%, where they believe it’s more likely to be incorrect than correct. The problem with this approach is that you’ll have to spend a lot more time and effort going much deeper to find errors — to the point where you might wonder if you should just do it yourself rather than hire someone. Without a healthy balance of optimism and pessimism, it’s hard to achieve a well-balanced approach.
