This episode is the latest in our monthly PM Talks series, where I’m joined by my friend Patrick Rhone to explore timeless ideas around productivity, creativity, and everything in between. In this conversation, we take a deep dive into what it really means to be creative—especially when you’re busy, overwhelmed, or stuck in perfectionism.

We unpack how constraints can fuel creativity, how time and space are both essential and elusive, and why imperfection might be your creative superpower. There’s a lot of riffing, real talk, and reflection in this one—and if you’ve felt like your creative well is running dry, this might be the refill you’ve been waiting for.

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Six Discussion Points

• The relationship between speed, structure, and creativity
• Why constraints can actually enhance creativity (yes, really)
• John Cleese’s insight: creativity requires both time and space
• How perfectionism can sabotage creative flow
• Turning mundane tasks into creative opportunities
• The importance of being your own audience—and knowing what’s “for you”

Three Connection Points

This episode is a reminder that creativity isn’t just for artists—it’s for anyone trying to make something meaningful with their time. Whether you’re juggling routines, deadlines, or just trying to show up a little more intentionally each day, the ideas we explore here can help unlock creative momentum—even in life’s most constrained moments.

Want to support the podcast? You can subscribe to the show and leave quick rating and review wherever you listen to podcasts. You can subscribe on Spotify and also on Apple Podcasts.

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Have you ever made a decision, only to immediately question whether it was the right one? I just forgot how to spell the word “Cheers” after including it in a congratulatory statement in a post online today. Then I said to myself why do I doubt if the spelling was wrong or correct? Second-guessing is caused by fear of failure, low self-confidence, overthinking, perfectionism, and social comparison. It often stems from anxiety about making the wrong choice.

While some degree of self-reflection can be beneficial, excessive second-guessing can lead to anxiety, indecision, and even missed opportunities.

So why do we do it? And how can we manage it effectively?

Why Do You Second-Guess Yourself?

Don’t say no, I am confident if you are reading this, you might have searched for it.

At its core, second-guessing is a defense mechanism meant to help us make thoughtful choices. However, when taken to the extreme, it can hold you back. Here are some of the key reasons we tend to second-guess our decisions, believe me, I related to these reasons as well.

1. Fear of Failure

One of the biggest drivers of second-guessing is the fear of making a mistake. When the stakes are high, we worry about the consequences of a wrong decision, which can lead to hesitation and self-doubt.

2. Low Self-Esteem

People who struggle with self-worth often question their judgment. They may attribute negative outcomes to personal failings rather than external factors, making them more prone to second-guessing.

3. Perfectionism

The desire to make flawless choices can be paralyzing. Perfectionists tend to overanalyze their decisions, constantly searching for an option that is “better,” even when their initial choice is already good.

4. Social Comparison

When we compare our decisions to those of others—especially in an age of social media—uncertainty creeps in. Seeing someone else make a different choice can make us doubt whether we’ve chosen the right path.

5. Overthinking

Replaying different scenarios in our minds can make us feel trapped in a loop of doubt. The more we analyze, the harder it becomes to trust our initial judgment.

6. Lack of Clarity

When information is incomplete or ambiguous, it naturally leads to uncertainty. Without clear facts or guidelines, it’s easy to second-guess our choices.

When Can Second-Guessing Be Beneficial?

Not all second-guessing is bad. In fact, some level of self-reflection can be helpful in making well-rounded decisions. Here’s when it can work in your favor:

1. Critical Reflection

A moderate amount of second-guessing allows us to identify potential flaws in our decisions. It gives us a chance to course-correct before it’s too late.

2. Considering Alternative Perspectives

Taking the time to weigh different options can help us make informed choices rather than acting on impulse. It encourages critical thinking and problem-solving.

How to Manage Excessive Second-Guessing

While some second-guessing is useful, too much of it can be paralyzing. Here’s how to keep it in check:

1. Identify the Source

Understanding why you second-guess yourself is the first step to managing it. Is it rooted in fear? Perfectionism? A lack of information? Identifying triggers can help you break the cycle.

2. Focus on the Decision-Making Process

Instead of fixating on whether your choice was “perfect,” remind yourself of the factors you considered when making it. If you made a thoughtful decision based on the best information available, trust it.

3. Build Self-Confidence

Regularly remind yourself of past successes and the times when your decisions turned out well. Self-affirmations and positive reinforcement can strengthen your belief in your own judgment.

4. Seek Support

If second-guessing is affecting your well-being, talking to a trusted friend, mentor, or therapist can provide reassurance and a fresh perspective. Sometimes, an outside opinion can help you see that your choice is more than reasonable.

Final Thoughts

Second-guessing is a natural part of decision-making, but when it becomes excessive, it can hinder progress and create unnecessary stress. By understanding its root causes and adopting strategies to manage it, we can move forward with confidence and clarity.

So the next time you find yourself doubting a decision, take a step back, trust yourself, and remind yourself that no choice is ever completely risk-free—but growth comes from learning, not from fear. Stay tuned to Age and Wealth

Introduction

Last week, my teenage son spent six hours rewriting the opening paragraph of his college essay. Six hours. On one paragraph. Watching him agonize over every word choice, I saw myself—and realized how deeply I’d passed down my perfectionist tendencies. That’s when it hit me: my pursuit of flawlessness wasn’t making me excellent. It was making me exhausted.

Here’s the cruel irony of perfectionism: it promises to make us exceptional, but instead it keeps us stuck. We tell ourselves we’re maintaining high standards, but what we’re really doing is building invisible prisons. Every unstarted project, every delayed decision, every “not quite ready yet” moment—they all add up to a life half-lived.

The good news? There’s a way out. I’ve discovered how to overcome perfectionism without becoming mediocre or careless. It means learning to channel that drive for excellence into actual progress. It means understanding the difference between healthy standards and self-sabotage.

Because here’s what I’ve learned after years of wrestling with this demon: learning how to overcome perfectionism isn’t about lowering your standards—it’s about raising your quality of life. And that transformation starts with understanding why your brain’s quest for perfection is actually its biggest limitation.

The Hidden Cost of Perfectionism

Here’s the thing about perfectionism that nobody talks about at work meetings: it’s actually making you worse at your job. I know, sounds backwards, right? But perfectionists spend so much time polishing that first paragraph, they never finish the report. Studies show they actually complete 30% fewer tasks than their “good enough” colleagues. It’s the ultimate productivity paradox.

The mental toll? It’s brutal. Research has found that perfectionism significantly increases your risk of anxiety and depression (American Psychological Association, 2018). We’re talking about real people here—maybe you—lying awake at 3 AM, replaying that slightly awkward email they sent. Nearly 70% of perfectionists experience burnout within five years of starting their careers. That’s not dedication; that’s self-destruction.

And relationships? Forget about it. Perfectionism creates this invisible wall where you can’t let anyone see the “messy” you. Partners feel like they’re dating a resume instead of a person. Friends stop inviting you to things because you’re always “too busy” perfecting something that was fine three drafts ago. Research shows perfectionists tend to have fewer close friendships due to their fear of vulnerability and judgment.

Career-wise, while you’re waiting for the “perfect moment” to apply for that promotion, three other people already got hired. Studies indicate that perfectionists apply to significantly fewer positions and take much longer to make career moves due to fear of rejection. Those “imperfect” risk-takers? They’re becoming your boss.

Physically, your body keeps score. Chronic perfectionism triggers constant cortisol release—hello, insomnia! About 65% report regular sleep issues, 80% experience tension headaches, and don’t get me started on the digestive problems from stress-eating or forgetting meals while chasing impossible standards. Your perfectionism isn’t just exhausting your mind; it’s literally breaking down your body.

Understanding Your Perfectionism Type

Think you’re just “a perfectionist”? Not quite. Perfectionism comes in three distinct flavors, and recognizing yours is the first step toward breaking free.

Self-oriented perfectionists are their own harshest critics. You set impossibly high standards for yourself, then beat yourself up when you inevitably fall short. That presentation wasn’t just good—it needed to be flawless. Sound familiar?

Other-oriented perfectionists project their standards outward. You expect perfection from everyone around you—your partner should anticipate your needs, your coworker should never make mistakes, your kids should excel at everything. This type often damages relationships without realizing it.

Socially-prescribed perfectionists live in constant fear of judgment. You believe others demand perfection from you, so you exhaust yourself trying to meet imaginary expectations. Every Instagram post needs the perfect caption. Every work email requires three rewrites.

Quick Assessment: Which thought appears most often in your head?
– “I should have done better” → Self-oriented
– “Why can’t they get it right?” → Other-oriented
– “What will people think?” → Socially-prescribed

Why does this matter? Because each type needs different strategies to overcome perfectionism. Self-oriented perfectionists must learn self-compassion. Other-oriented types need to practice acceptance and realistic expectations. Socially-prescribed perfectionists have to challenge their assumptions about others’ judgments.

You might recognize yourself in multiple types—that’s normal. Most of us have a primary type with secondary tendencies. The key is identifying your dominant pattern so you can target it effectively.

The Neuroscience Behind Perfectionism

Think of your brain as a well-meaning but overprotective parent. When faced with potential failure, your amygdala—the brain’s alarm system—floods you with fear signals, screaming “Danger! Your reputation is at stake!” This fear response, originally designed to keep us safe from predators, now fires up when we spot a typo in our email or receive constructive feedback.

Here’s where it gets tricky: Every time you achieve perfection, your brain releases dopamine—that feel-good chemical that makes you crave more. It’s like giving a cookie to a child every time they cry; soon, they learn that crying equals cookies. Your brain learns that obsessive checking, endless revising, and sleepless nights equal that sweet dopamine hit.

Over time, these patterns literally reshape your neural pathways. The perfectionism highway in your brain becomes a six-lane superhighway, while the “good enough” path turns into an overgrown trail. Your brain defaults to the familiar route, even when it leads to exhaustion and anxiety.

But here’s the beautiful plot twist: neuroplasticity. Your brain can build new highways at any age. Every time you choose “done” over “perfect,” you’re laying down new neural pathways. It’s like learning a new language—awkward at first, but with practice, it becomes second nature.

How to Overcome Perfectionism: The 5-Phase Method

I’ve spent years watching brilliant people sabotage their own success, waiting for the “perfect moment” that never comes. After coaching hundreds of recovering perfectionists, I’ve developed a battle-tested method that actually works. Here’s your roadmap to freedom.

Phase 1: Awareness Through Pattern Recognition

The first step is catching yourself in the act. Start a “perfectionism log” for one week. Every time you delay, overthink, or redo something, write down: the trigger, your thoughts, and what you were afraid would happen if it wasn’t perfect.

You’ll discover your “perfectionism voice” – that internal critic with very specific phrases. Mine says things like “This isn’t professional enough” or “What will they think?” Once you identify these patterns, you can’t unhear them.

Try this cost-benefit analysis: List what perfectionism gives you (quality, pride) versus what it costs you (time, opportunities, stress). Most people are shocked when they see the real price tag of their impossibly high standards.

Phase 2: Rewiring Your Standards

Here’s a mind-bender: 80% quality delivered consistently beats 100% quality delivered never. Your new mantra? “B+ work that ships beats A+ work that doesn’t exist.”

Start setting “good enough” benchmarks before you begin any task. For emails: one proofread, send. For presentations: clear message, supporting data, done. For creative projects: does it serve its purpose? Ship it.

Create a “Done and Dusted” celebration ritual. When you finish something at 85% instead of endlessly polishing, do a victory dance, text a friend, or add a gold star to your calendar. Your brain needs to learn that “good enough” deserves rewards too.

Phase 3: Action Over Analysis

The “Messy Action” method saved my business. Set a timer for 25 minutes and work on something you’ve been perfecting for weeks. When the timer rings, you must share it, submit it, or publish it. No exceptions.

Time-boxing is your new superpower. Give yourself half the time you think you need. Parkinson’s Law states that work expands to fill the time given – so give less time. You’ll be amazed at what you can accomplish when perfection isn’t an option.

Public accountability changes everything. Tell someone about your imperfect action plan. Post your rough draft. Share your messy progress. When others see your journey, perfectionism loses its grip.

Small wins compound. Shipping one imperfect blog post leads to insights for the next one. Each “good enough” project builds evidence that the world doesn’t end when you’re not perfect.

Phase 4: Embracing Productive Failure

Mistakes aren’t failures; they’re data collection. When something doesn’t work, ask: “What did I learn?” instead of “What’s wrong with me?” This simple reframe transforms setbacks into setups.

Create a “failure resume” – a list of your mistakes and what they taught you. My biggest business flop taught me more about market research than any success could have. Your failures are your most expensive education; might as well use it.

Develop a “mistake ritual.” When you mess up, do ten pushups, donate $5 to charity, or write one lesson learned. This transforms the emotional sting into productive action. You’re training your brain that mistakes equal growth, not shame.

Phase 5: Sustainable Excellence

Stop seeking perfection; build systems instead. A good system performed consistently outperforms sporadic bursts of perfection every time. Focus on processes you can repeat, not one-time performances you can’t sustain.

The compound effect is real. Publishing weekly at 75% quality for a year beats publishing quarterly at 95% quality. Consistency creates excellence, not the other way around.

Define “done” for yourself. Write your personal definition and stick it somewhere visible. Mine is: “When it serves its purpose and I’ve given my current best effort within the time available.” What’s yours?

Remember: perfectionism is fear wearing a quality costume. This method isn’t about lowering your standards – it’s about raising your output. You’re not becoming mediocre; you’re becoming prolific. And in a world drowning in unfinished perfection, the person who consistently ships good work wins.

Start with Phase 1 today. Your future self will thank you for every imperfect action you take.

Practical Exercises for Daily Practice

Learning how to overcome perfectionism requires consistent, small actions. Here are four exercises that have helped thousands rewire their relationship with “good enough.”

Morning Intention Setting: Start each day by writing one sentence: “Today, I will complete [specific task] to 80% quality.” This primes your brain to value completion over perfection. For example: “Today, I will finish my presentation slides to 80% quality by 2 PM.”

The Progress Journal: Keep a simple notebook where you record three things daily: what you started, what you continued, and what you finished—regardless of quality. This shifts focus from perfection to momentum. Don’t judge the entries; just document your forward movement.

Evening Reflection Questions: Before bed, ask yourself: “What did I ship today that wasn’t perfect?” and “How did that feel?” These questions celebrate imperfect action and help you process the emotions around letting go of unrealistic standards.

Weekly Experiments in Imperfection: Choose one low-stakes area each week to deliberately do “poorly.” Send emails without triple-checking. Post social media content with minor typos. Cook dinner without following the recipe exactly. These controlled experiments prove the world doesn’t end when you’re imperfect.

When to Seek Professional Help

While self-help strategies work for many, perfectionism sometimes requires professional support—and that’s perfectly okay.

Consider therapy if perfectionism causes persistent anxiety, depression, or significantly disrupts your work, relationships, or daily functioning. If you’re avoiding important tasks entirely, experiencing physical symptoms like insomnia or headaches, or having thoughts of self-harm when you “fail,” it’s time to reach out.

Cognitive Behavioral Therapy (CBT) and Acceptance and Commitment Therapy (ACT) show excellent results for perfectionism. Many therapists specialize in perfectionism and high-achieving clients. Start with Psychology Today’s therapist finder, filtering for your specific needs. Your employee assistance program or insurance provider can also provide referrals. Remember: seeking help is a sign of wisdom, not weakness.

Conclusion: Your Imperfect Action Plan

If you’re wondering how to overcome perfectionism, know this: it isn’t serving you—it’s stealing from you. We’ve explored how it masks as excellence while breeding procrastination, how embracing “good enough” creates momentum, and how progress beats perfection every single time.

Here’s your 30-day challenge: Choose one area where perfectionism paralyzes you. Maybe it’s that business idea, fitness routine, or creative project. For the next month, take one imperfect action daily. Send that rough draft. Do that 10-minute workout. Write that messy first page.

Imagine life without the weight of impossible standards. Picture yourself shipping projects, building relationships, and actually enjoying the journey. As a CEO and father, I’ve learned that my sons don’t need a perfect dad—they need a present one who models courage over caution.

Your perfectionism ends today. That thing you’re overthinking? Do it badly. Do it scared. But do it now. Because messy action today beats perfect plans tomorrow.

Start messily. Start now. Start living.

“You yourself, as much as anybody in the entire universe, deserve your love and affection.”
Buddha

“People throw away what they could have by insisting on perfection, which they cannot have, and looking for it where they will never find it.”
Edith Schaeffer

One common way to get things done, to achieve and to motivate yourself is to be kind of hard on yourself.

To set very high standards for yourself that you want to stick to every time.

Now, this way of going about things can indeed help you to accomplish big things in your life and to get things done every week.

But it comes at a price.

Three negative things about taking this position towards yourself are:

You tear your self-esteem down. 

As you achieve things you tend to tear down your own self-esteem at the same time.

So you feel less and less like you deserve success. And frustration and being angry can become more and more common as you fail to reach those very high standards.

You suck the fun and excitement out of things.

A hard or harsh attitude towards yourself has a tendency to make things that used to be fun and exciting less and less so.

This attitude does instead over time turn those things into just work that you may start to dread because you fear failure or not meeting your high standards.

You’ll perform worse and worse.

As your self-esteem goes down you’ll feel less motivated to tackle the tasks and projects in your life. As the fun and excitement goes out of many of the things you do procrastination tends to become more and more common.

Plus, the work you put in becomes less energetic and focused and so the results aren’t that good anymore either.

I used to take the harder and harsher path. It did help in some ways. But it wasn’t worth it.

So what can you do if you feel that you are maybe too hard on yourself or you beat yourself up quite often?

Here are 4 tips that helped me to become kinder towards myself, to get more of the most important things done and to feel better about myself and my life.

1. Remind yourself of the negative effects of this attitude.

To just remind yourself of how damaging being hard on yourself has been is in my experience a very effective way to replace the old habit with going easier on yourself.

2. Go for more human and smarter standards for yourself.

Movies, books and the people around you may push standards on you that are just pure fantasy or some kind of perfect dream.

But life is life, not a fantasy or dream and to set such extremely high standards that no one can live up to just leads to what you may see as failure and disappointment in yourself and in your life.

Instead, relax a bit and accept that everything and everyone has flaws and things don’t always go as planned.

Accept that you can still improve things but they will never be perfect.

And realize that you won’t be rejected if things or you aren’t perfect. At least not by reasonably well-balanced human beings, like most people actually are in reality.

3. Focus on the positive and helpful feedback in setbacks.

It is very common to be hard on yourself when you make a mistake or fail.

But it is also a very destructive habit because it can magnify one such event into something that makes you feel depressed for days or weeks or makes you quit altogether.

So when you are hard on yourself for a failure or mistake then relax a bit and go a bit easier on yourself. Remind yourself of why this is a much better strategy to keep the motivation and self-esteem up.

And ask yourself:

• What is one thing I can I learn from this situation?
• How can I use what I learn from this to not make the same mistake again and to move forward in a smarter way?

4. Celebrate your small steps of forward.

If you are in the habit of only celebrating when you reach a big milestone or a perfect moment or two then you may lose your motivation and feel like you are never happy or arriving where you want to be.

So make a habit of celebrating your small daily and weekly successes too.

This will help you to keep the soul-tiring monotony away and help you to stay enthusiastic instead of getting more and more unmotivated until you may even consider quitting halfway to that big milestone.