Eli sat in front of his laptop, staring at a nearly finished proposal for a potential client. He’d been at it for hours—tweaking a phrase here, shifting the layout there, rewriting sentences that were fine the first time. The funny part? The client wasn’t paying him for perfect grammar or a flawless design. They wanted his creative approach to a problem. But Eli had hooked onto a detail loop, and now he was at risk of missing the submission deadline altogether.
Sound familiar?
For many entrepreneurs, overthinking and perfectionism are invisible productivity killers. While hustle culture glorifies “sweating the details,” in practice, circling endlessly around the same project prevents you from moving forward. You’re not bouncing between opportunities—you’re polishing, stalling, and second-guessing.
Why Entrepreneurs Overthink
Running a business is high-stakes, and when the stakes feel high, the brain defaults to caution. Overthinking becomes a defense mechanism: “If I just polish this idea a little more, I’ll protect myself from criticism.”
But here’s the trap: the more time spent overthinking, the less time you spend testing, learning, and iterating in the real world. That’s where growth happens.
Harvard Business Review once noted that perfectionism can masquerade as a strength but actually leads to procrastination and stress (HBR article on perfectionism). For founders and leaders, that stress gets compounded when it stalls momentum.
Perfectionism in Disguise
Sometimes overthinking doesn’t look like perfectionism at all. It can show up as:
Never sending the email because you’re waiting for the “perfect” wording.
Redesigning your website for the third time instead of launching your service.
Over-researching every possible outcome before making a decision.
The cruel irony is that clients, investors, or customers often value speed and authenticity over spotless execution. In fact, LinkedIn’s founder Reid Hoffman famously said, “If you are not embarrassed by the first version of your product, you’ve launched too late.”
The Overthinker’s Survival Guide
Overthinking feels productive, but it’s really disguised procrastination. Here’s how to break the cycle:
Set a Deadline for Decisions Give yourself a specific time frame: “I’ll polish this for 30 minutes, then it’s done.”
Redefine “Done” Done doesn’t mean flawless—it means ready for feedback, testing, or launch.
Shrink the Task Break a project into smaller pieces so you can ship something quickly instead of stalling on the whole thing.
Use External Accountability Tell a colleague, coach, or friend when you’ll hit “send.” Accountability creates momentum.
Interrupt the Loop If you’re spiraling, step away: change location, take a short walk, or switch mediums (talk it out, record a voice note).
Ask the 80/20 Question What 20% of effort will create 80% of the result? Focus there and let go of the rest.
Remember the Opportunity Cost Every extra hour spent perfecting one thing is an hour lost to growth, rest, or creativity.
And if you want more science-backed strategies, psychologist Thomas Greenspon has written extensively about the perfectionism trap (APA overview on perfectionism). His takeaway: perfectionism doesn’t improve performance—it stifles it.
Progress Over Perfection
Back to Eli. Eventually, he decided to set a two-hour timer and force himself to send the proposal when it rang. The client loved it—and didn’t notice the small “imperfections” Eli had obsessed over. That experience taught him something many entrepreneurs eventually learn: momentum matters more than microscopic details.
Overthinking feels like working hard, but it’s really just spinning your wheels. The cure isn’t lowering your standards—it’s recognizing that progress, feedback, and iteration will get you further than perfection ever will.
If you see yourself in Eli’s story, ask: Do I need help working through my tendency to overthink and insist on perfection? Consider CoreCoaching. Contact me at Rebecca@MindfulCommunication.com The answer may just be the key to unlocking your next big leap forward.
In his recent DarrenDaily episode titled “The Fatal Flaw in Smart Decision-Making,” success mentor Darren Hardy sheds light on a common trap that even high-achievers fall into: the paralysis of overanalyzing decisions in pursuit of perfection. His core message? “Perfect decisions made too late are the same as wrong decisions.”
This insight challenges the popular belief that smart decision-making is about always getting it right. Instead, Hardy argues that timely action is far more valuable than flawless execution. Waiting for the “perfect” choice often results in missed opportunities, delayed progress, and stunted growth.
To support his point, Hardy references well-known leaders who embrace speed over perfection. One powerful example is Jeff Bezos, founder of Amazon. Bezos has famously promoted a principle he calls “disagree and commit” and often refers to making decisions with “70% of the information.” His view is that waiting for 90% or more of the data can slow down innovation and responsiveness. In his annual shareholder letters, Bezos emphasizes that “speed matters in business” and that being wrong isn’t as costly as being slow. This bias toward action has been central to Amazon’s culture of experimentation and rapid scaling.
Similarly, Hardy nods to leaders like Abraham Lincoln, who made bold and timely decisions in the face of uncertainty during the Civil War, and Elon Musk, who is known for moving quickly and iterating based on results—even when it means taking calculated risks.
So how can we escape the trap of perfectionism and become more decisive? Hardy recommends four key strategies:
Set Clear Deadlines: Give yourself a time limit for making each decision. This reduces the temptation to endlessly analyze.
Embrace Imperfection: Recognize that no decision is ever 100% right. The goal is momentum, not flawlessness.
Prioritize Action: Execution brings clarity. Even a mediocre decision, when acted upon, can lead to real progress and better insight.
Learn and Adjust: Decisions should be followed by reflection. Use what you learn to improve future choices—this is how true mastery is built.
To wrap it up, Hardy challenges his audience with three questions:
What decision will you make in the next 24 hours?
What action will you take today?
What perfectionism will you let go of?
These are not just rhetorical questions—they’re invitations to break free from decision paralysis and step into bold, imperfect action.
In essence, Hardy’s message is simple but profound: You don’t need perfect decisions—you need timely ones. Whether you’re leading a company or leading your own life, adopting this mindset can be the key to real momentum and long-term success.
You may ask, “What is the 70% of the information I need to know to make a smart but speedy decision?” These are some of the topics we discuss in CoreCoaching. Contact me at Rebecca@MindfulCommunication.com. Visit my website at www.MindfulCommunication.com
When Victor Hugo, the playwright, procrastinated and wanted to go out to a café instead of writing, he coaxed himself to get work done by having a servant take away all his clothes and return them only until he completed his work. A bit extreme, but it worked.
It’s tax season, time to get back to the gym, plus all the other things you may be putting off. Don’t fret, keep your shirt on! I have a better solution. Check out my 80→20 Nocrastination tool.
Go to my websitewww.MindfulCommunication.comand hit the TOOLS menu. Open the 80→20 Nocrastination Tool. No downloads, and it’s free!
The 80→ 20 tool will walk you through the steps to get started on the task you are putting off. My clients describe procrastination as an ever-widening deep, scary chasm between them and the start of the task. The gap is filled with potential obstacles: uncertainty, boredom, the fear of failure and the dreaded emotions that accompany them. The longer you put off a task the greater the gap.
The 80→20 gets you started, and gently guides you through each step towards DONE. The 8 questions (the 80%) gradually clear the obstacles making the task more approachable. The last 2 steps (the 20%) help you follow through to DONE. The process is easy and can move quickly. Every step narrows the gap and eases the stress.
Give the 80→ 20 a try. I would love your feedback!
Still stumped by procrastination? Seriously? Contact me at Rebecca@MindfulCommunication.com
Len wants to leave his job to start his own design studio. As Len smartly assesses his entrepreneurial readiness, he wants to rid himself of one habit that could doom his startup — perfectionism.
Mark Cuban of the TV series Shark Tank said, “Perfectionism is the enemy of an entrepreneur.” It cannot be cured over night, but can be broken down gradually through coaching.
Frustrated with the indecisiveness and stress that come with perfectionism, Len agreed to apply a strategy to a current problem: Len owes HR five staff performance reviews (perfs) by the end of the week. They are six months overdue.
In light of other tasks that beg for Len’s attention, I asked him to describe what an “adequate” perf would look like. Would it sufficiently meet the expectations of the employee and HR? How much time would it take to do each one? Len could not identify any downsides to an adequate perf.
A “perfect” perf would include more flowery language and several links to training videos that would likely be ignored. Compared to an adequate perf, Len admitted that a perfect perf was excessive and a poor use of time with no upsides.
Contrasting the two versions in terms of time and benefit was a practical step towards tempering Len’s perfectionism. It eased the ability to get started and complete the task in time.
Perfectionism may require more than coaching, however. It is essential to manage this behavior efficiently before starting your own business. Contact me at Rebecca@MindfulCommunication.com
Rebecca’s CoreFour Coaching
"It takes more than courage to be an Entrepreneur, it takes CORE." Find out more.
Cookie Consent
We use cookies to improve your experience on our site. By using our site, you consent to cookies.
ID used to identify users for 24 hours after last activity
24 hours
_gat
Used to monitor number of Google Analytics server requests when using Google Tag Manager
1 minute
_gali
Used by Google Analytics to determine which links on a page are being clicked
30 seconds
_ga_
ID used to identify users
2 years
__utmx
Used to determine whether a user is included in an A / B or Multivariate test.
18 months
_ga
ID used to identify users
2 years
__utmz
Contains information about the traffic source or campaign that directed user to the website. The cookie is set when the GA.js javascript is loaded and updated when data is sent to the Google Anaytics server
6 months after last activity
__utmv
Contains custom information set by the web developer via the _setCustomVar method in Google Analytics. This cookie is updated every time new data is sent to the Google Analytics server.
2 years after last activity
__utmc
Used only with old Urchin versions of Google Analytics and not with GA.js. Was used to distinguish between new sessions and visits at the end of a session.
End of session (browser)
__utmt
Used to monitor number of Google Analytics server requests
10 minutes
__utmb
Used to distinguish new sessions and visits. This cookie is set when the GA.js javascript library is loaded and there is no existing __utmb cookie. The cookie is updated every time data is sent to the Google Analytics server.
30 minutes after last activity
_gac_
Contains information related to marketing campaigns of the user. These are shared with Google AdWords / Google Ads when the Google Ads and Google Analytics accounts are linked together.
When Victor Hugo, the playwright, procrastinated and wanted to go out to a café instead of writing, he coaxed himself to get work done by having a servant take away all his clothes and return them only until he completed his work. A bit extreme, but it worked.
Len wants to leave his job to start his own design studio. As Len smartly assesses his entrepreneurial readiness, he wants to rid himself of one habit that could doom his startup — perfectionism.
"It takes more than courage to be an Entrepreneur, it takes CORE."