my biggest critic (exposed)

From harsh inner critic to wise mentor: transforming self-criticism, finding joy in high performance, and building a sustainable path to excellence

My biggest critic finds flaws in everything I do, even during my best moments.

I remember riding home after winning a big rugby game, only for my critic to fixate on that one missed tackle or bad pass.

When I was young, this criticism was mostly limited to occasional low-stakes rugby games. As I got older, my critic began hovering over my shoulder at work, scrutinizing my productivity, critiquing my pitch decks, and waiting off-stage after speaking events to remind me of every fumbled word and mispronunciation.

You see, as long as I can remember, I've been my own harshest critic.

Having played alongside varsity athletes and worked with high-level entrepreneurs, I'm not unique in this—quite the opposite.

For those with ambitious goals, we often unnecessarily shoulder the weight of the world. This burden eventually steals the joy from our pursuits, as the fear of self-criticism becomes our primary motivator—hardly a healthy drive.

I see this pattern in the founders I work with:

  • CEOs who can't celebrate wins with their team because they're fixated on minor setbacks

  • Entrepreneurs who burn out chasing an impossible standard of perfection

  • Athletes who forget why they fell in love with their sport in the first place

The truth is, self-criticism has been both my kryptonite and my superpower. That same inner voice that pushed me to excel in rugby, start new businesses, and get better everyday… is a bit of an asshole at times.

Here's the challenge: not silencing this voice, but refining it.

The path forward is about transforming raw self-criticism into constructive self-awareness:

  1. Redefine success: While maintaining high standards, shift your focus from perfection to consistent progress. Embrace the Stoic mindset—expect challenges and focus on what you can control. In rugby, for instance, nobody plays a perfect game, so concentrate on bouncing back from mistakes rather than beating yourself up.

  2. Create breathing room: Balance productivity with intentional breaks. Rather than frequent small rewards throughout the day, establish meaningful milestones and celebrate them properly. Set aside dedicated time - like Friday nights - for genuine rewards, whether it's date night or solo relaxation. This makes achievements feel more significant and sustainable.

  3. Practice self-compassion and selective hiring: I learned this the hard way. In the past, I tiptoed around setting high standards with employees because I didn't want to be an "asshole boss"—having experienced those bosses myself. Here's the problem: if you hire people whose ambition and drive don't align with yours, you'll harbor resentment, even when they're doing a good job. But when your team naturally pushes themselves toward excellence, you don't need to be the constant taskmaster. This isn't about lowering standards—it's about creating a culture of sustainable growth through aligned motivations.

Remember: The goal isn't to silence your inner critic—it's to transform that voice from a harsh internet troll into a wise mentor.

After all, true excellence comes from knowing when to push yourself and when to step back.

idea of the week 💡

  • problem: Gym-goers struggle to maintain proper form during exercises, leading to ineffective workouts and potential injuries. Traditional mirrors and recording yourself aren't optimal solutions.

  • idea: AI-powered fitness app that uses your iPhone camera to provide real-time form feedback during workouts. Uses computer vision to analyze movement patterns and gives voice cues for corrections. Could integrate with Apple Health and allow trainers to remotely monitor client form through recorded sessions.

  • how it makes money: Freemium model with basic features free, premium subscription ($9.99/month) for advanced form analysis, trainer integration, and progress tracking. Additional revenue through trainer marketplace (15% commission).

  • why it might fail: Accuracy might be limited by phone camera placement and angles. Market is saturated with fitness apps, making user acquisition expensive.

workout of the week

Three different workouts to challenge yourself this weekend:

at-home workout:

Complete 5 rounds:

  • 25 alternating jump lunges (total)

  • 15 close-grip push-ups

  • 20 v-ups

  • 45-second plank hold

Rest 90 seconds between rounds

gym workout:

  • 5x5 barbell rows

  • 4x10 front squats

  • 3x12 incline dumbbell press

  • Finisher: 100 burpees for time

outdoor workout:

Complete 4 rounds:

  • Run 400m

  • 20 box jumps (park bench)

  • 15 decline push-ups

  • Bear crawl 40m

Rest 2 minutes between rounds

tweet of the week

Always nice to hear this type of life advice from someone who can afford the private jet or fancy car (Tim)

my plugs