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Perfection is the Enemy of Progress
The title is a quote from Winston Churchill. I have learned in my career that these behaviors can be very costly from a business perspective, especially when decisions affect large parts of a business. It took me years to learn this lesson as I transitioned from perfectionist to “reformed perfectionist,” which was challenging.
Below are a few examples that could help you better understand people like this, and if you are someone like this, it might even provide motivation to try to change.
Early in my career, as I expanded my role from Programmer to Analyst Programmer to Systems Analyst, I often found myself spending too much time and effort on things that had minimal impact. Applications and subsystems looked a little better, ran a little faster, integrated more easily, were easier to modify, and generally had fewer problems. Those are all good things, but in hindsight, those benefits often did not justify the associated costs.
Some industries and applications require a degree of quality and reliability, such as nuclear power plants and lifesaving medical equipment. Since very few things are perfect, there are usually a variety of built-in safeguards to mitigate the impact of errors and failure. I have worked on a few of those systems, and I get it. But they are not in the majority.
Identifying the intersection of meeting the stated requirements, delivering the required quality, and knowing what “good enough” looks like is essential. That’s where diminishing returns set in for every additional hour spent on an activity.
I worked with a hardcore perfectionist at a small software and services company. On a consulting engagement, he spent two days on a task that I viewed as a 2-4 hour effort. We discussed it, and he told me he had at least three more days to finish. We had a heated discussion, and he was frustrated with me for a while. Years later, he admitted I was right, talked about how difficult it was to change, and how much more productive he is now.
I had a consulting engagement with a small software company that spent 10+ years on a SaaS product and was always “just two to three weeks away” from their MVP (minimum viable product). I started working with them over three years ago, and they are still at that point today. Software is never perfect, so waiting for perfection can kill a company.
I have also sold to companies stuck in analysis paralysis because they (leaders and teams) are always second-guessing decisions and want to be 100% certain before making a decision. Those companies need to solve a problem, or they would not be seeking a solution. In most cases, making an informed decision on a proven solution now will solve their problems and deliver value quickly. There is an actual business cost for every month of delay.
Are these behaviors costing you or your company money? If yes, dig a little deeper to understand the potential positive impact making small changes could have. Daily improvement is a great thing!
Success is a Mental Game
This assertion is as true in business as in sports, individually and in teams. So, let’s break it down.

When I watch my local football team, I occasionally see a shift in facial expressions from excitement to frustration – often right before the end of the first half. Sometimes, they recover during halftime and come out renewed and ready to win, but the “gloom and doom” expressions usually translate into suboptimal performance and mistakes. It is frustrating because you know they have the talent to win.
The same thing happens in business – especially in Sales. Sometimes it occurs in the middle of a sales cycle, similar to the example above. Unfortunately, too many people allow a few data points to determine their future trajectory. Why is that?
Whether you own a company or manage a group of people, good leaders aim to optimize their workforce by balancing factors that lead to happy, loyal employees doing their best for themselves, their customers, and their company. Many motivational theories exist, such as Expectancy Theory, Reinforcement Theory, the Role of Instrumentality, Intrinsic vs. Extrinsic Motivation, and more. Since one size rarely fits all, the challenge becomes reward-focused personalization, which can be a lot of work.
People will often win or lose before they even start. Their negativity, self-doubt, and anticipation of failure become a self-fulfilling prophecy. This post focuses on self-motivation, attitude, mindset, and creating the habits that lead to better success.
Below are four simple questions that someone should ask themselves when they question their ability to succeed in a position, company, or industry. There are always many ways to point the finger of blame elsewhere, but the first step should be to look in the mirror.
- Do you believe that you can win where you are today? If not, why are you still there? Customers and prospects can sense insincerity, so if you don’t believe in yourself, you shouldn’t expect them to believe in you. Maybe the company is terrible, and everyone is failing. If that is true, then it is probably time to look elsewhere.
- What have you learned from past successes and failures, and how have you adapted based on those lessons learned?
- What are some early indicators of success or failure that you have identified? Are you adapting to the situation if you run into those indicators now? The best approach may be to cut your losses on this attempt and move to the next sooner rather than later (i.e., qualify out quickly).
- What are you doing to improve your skills? It is funny how small, continuous improvement efforts lead to a greater sense of confidence. Greater confidence often translates to increased success.
I have found that consistently doing the right things is the best way to maximize my success. Start developing habits and routines that have led to winning in the past, but don’t expect them to work forever. Everything changes, and you should change, too. Look for what’s working for others, try it out, and if it works, incorporate it into your routines.
Success truly is a mental game, and everyone can win. The person who keeps winning over time is the one who doesn’t get stuck in time. Be curious, get excited, and adapt. And once you get there, start helping others. Having mentors is nice, but it is also great to become one.
As the saying goes, the rising tide lifts all boats. Winning can be a team sport, but it begins with individual contributors having winning attitudes. Unfortunately, the same is true of losing, so decide now what you want and move forward with energy and confidence.
Acting Like a Startup
Over the years, I have heard comments like, “We operate like a startup,” “We act like a startup,” and “We are an overnight success that was 10 years in the making.” These statements are often euphemisms for “We are small and not growing as quickly as we would like.”
There are numerous estimates of startup and failure rates in their first few years. One of the best descriptions I have found is from Failory. Investopedia and LendingTree have similar but differing takes on the statistics and root causes. The net result is that failure is much more common than success, especially over time. So, “acting like a startup” is not necessarily good, even when true. Instead, you want to “act like a successful startup!“
Understanding the various causes and the data on success and failure should become significant inputs to business plans focused on long-term success. As a Founder, there are several points that I believe to be key to success:

- You have specific expertise that is in demand and would be valuable to an identifiable number of prospective customers. How would those customers use those skills, and how would they quantify the value? That understanding provides focus on what to sell and to whom.
- A detailed understanding of the market and key players is needed to hone in on a niche to succeed.
- Understand your strengths and weaknesses, then hire the most intelligent and ambitious people who complement your weaknesses and strengths.
- Understand how to reach those potential customers and the messaging you believe will compel them. Find a way to test and refine those assumptions as necessary – before you go all in. Remember, Marketing and Lead Generation are very important but also expensive, so it pays to get this right the first time.
- Have a plan for delivering on whatever you sell before you get your first sale. A startup needs to develop its track record of success, beginning with its first sale.
- Cash flow is king. It is far too easy to run out of money while looking at an excellent balance sheet because of receivables. Understand what matters and why.
- Founders need to understand the administrative side of a business – especially the financial, legal (especially contract law), insurance, and taxes. Find experts to validate your approach and fill in knowledge gaps.
- Consistency leads to repeatable success. You standardize, optimize, and automate everything possible. Wasted time and effort become wasted opportunities.
- Finally, there needs to be sufficient cash on hand to fund the time it takes to find and close your first deals, deliver and invoice the work, and then receive your first payments. That could easily be a 3-6 month period.
Those are the foundational items that are reasonably tangible. What is not as concrete but equally as important are:
- Having or developing the ability to spot trends early and identify gaps that could become opportunities for your business.
- An agile mindset allows you to pivot your offerings or approach in order to refine your business model and hone in on that successful niche. Don’t fall into a sunk-cost fallacy.
- Foster a sense of innovation within your business. Always look for opportunities to deliver a better product or service, improve the efficiency and effectiveness of your business, and create intellectual property (IP) that adds long-term value.
- Focus on being the best and building a brand that helps differentiate you from your competition.
- Become a Leader, not a Manager (lead people, manage processes). Create your vision of success, set expectations for each person and team, and help eliminate roadblocks to their success. Trust your team to help you grow and replace members quickly if it becomes clear they are not a good fit.
Steve Jobs once said, “It doesn’t make sense to hire smart people and then tell them what to do; we hire smart people so they can tell us what to do.” To grow, you need to choose the best people you can afford, guide them, and trust them to perform in the best interest of your company. That is true in any size organization.
Winning is hard, so focus on the journey. Making your customers’ lives easier and allowing your employees to be creative while doing something they are proud of will lead you to your destination. But when things start going well, don’t sit back and convince yourself you are successful. Instead, feel the pressure of the competition – they are out there – and continue to focus on ways to improve and grow.
Success means different things to different people, but longevity, growth, profitability, and some form of contributing to the greater good should be dimensions of success for any vision.
Diverse Testing for the Best User Experiences
Long before I began consulting, I was developing new applications for a Marketing company. Nearly everything was built from the ground up then, and there was very little reuse. That changed over time as I developed reusable functions and eventually created a “standard system” that significantly reduced development time due to reuse. Throughout this multi-year period, I had an unplanned but valuable assistant – “Wendy”
My user interfaces were generally well received for their layout, workflow, help screens, etc. But a new hire on the Customer Service team consistently ran into problems. I was young, and one of my first interactions with her probably went something like this: “Why would you do it that way? That doesn’t even make sense? Have you ever worked with computers before?”

She began crying. I felt like a jerk as my frustration began to wane. Days later, I realized Wendy was a gift and not a problem. She had an incredible knack for finding obscure flaws and breaking things. I embraced it, bought her lunch, and asked her to help improve my software. She was excited to help, and eventually we laughed about our initial encounters.
Wendy and I had become allies in a quest to create custom software that provided a better, problem-free user experience. Nothing was taken for granted. Everything became more robust. Surprisingly, everyone appreciated these changes, not just Wendy. She helped me become a better programmer and analyst, and I gave her an experience that helped her become one of the first Quality Assurance Analysts in the company. It was a win-win.
There is often a considerable difference in the expectations and ways that Gen Z, Millennial, Gen X, and Baby Boomer users interface with applications. Creating a one-size-fits-all application is far more challenging today because of this simple fact. But it is essential to success.
People today tend to move on when their experiences fail to match their expectations. Investing in your system’s “Wendy-proofing” can become a competitive advantage. I have long believed that “People buy easy.”
If one person encounters a problem, others will likely follow unless you implement a remedy. It is more work, but the result can be increased satisfaction, usage, and loyalty. That seems like a good tradeoff to me.
What are your thoughts?
Spaces Learning — Composable Education in the Cloud
Great article.
This is an extremely powerful Teaching and Learning Experience Platform (LXP) that I have been using for close to a year now. It is amazing how a better approach to learning leads to better retention and understanding.
“Tell me and I forget. Teach me and I remember. Involve me and I learn.”
Benjamin Franklin
Life is filled with unexpected events. In most cases, we make tiny adjustments and carry on. We trip. We stumble. We pick ourselves up and pay closer attention to where our feet are taking us.
Others force us to rethink what we previously took for granted. These are the big events that come out of the blue, grab us by the collar, and give us a good shaking. The death of a loved one. The sudden loss of a job.
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