More Conversations Like This: Sitting Down With Andy Reid on Success Curious

I was recently a guest on the Success Curious Podcast with Andy Reid, and I'm really happy to have had that conversation. Andy opened with an introduction that I told him was probably in my top five intros of all time, which set the tone for the rest of it. He's run well over a hundred episodes, asks every guest the same question about what a successful human looks like, and doesn't mind letting a conversation wander off the planned format when something more interesting turns up. Ours did that more than once. He called it a ride into the wilderness, intellectually, and that's about right.

You can listen to the full episode on Spotify. What follows is a written version of the parts I found most worth sitting with, for anyone who'd like to skim first.

We covered a lot of ground. Awareness over discipline, what fulfilment actually means, whether data or intuition should steer a decision, the idea that we're all live streaming life in the present moment, why familiarity keeps people in scarcity, what phones are doing to our identity, and the one thing I still need to get better at. Jump to whichever part catches you using the timestamps below, or listen from the start.

Who this conversation is for

Founders and operators who are good at execution and have started to wonder what it's all pointed at. If you've noticed your discipline covering for something, or hit a goal and felt oddly flat, a few of these threads will be familiar.

What we covered

Timestamps are approximate and follow the transcript.

• 00:31 Andy's introduction
• 02:30 Who I am and how I got into working with founders
• 04:12 Where conviction comes from, and why your word has to mean something
• 07:58 Awareness over discipline
• 11:27 Andy's question: what is a successful human?
• 13:33 What defines the core areas of a fulfilling life
• 15:02 Being adaptive and staying focused
• 20:33 Data, intuition and the live stream of now
• 27:12 Familiarity, scarcity and abundance
• 34:20 Smartphones and identity
• 42:51 A time I lost awareness of who I was
• 46:32 The one thing I need to get better at

The questions that stayed with me

Where does your confidence come from?

Andy started here, and it took me back to a rough stretch of my younger years. What I took from that period is that your word has to mean something. If you say you'll do something, you follow through. In business that gets tested over years rather than weeks. Anyone can come in hot and promise everything, but time reveals all, and five or ten years later the people who never followed through have used up their reputation, because people talk. Training keeps me honest in a similar way. You can't lie to the weights.

Do you believe in discipline?

Andy said he doesn't personally believe in discipline in the way most coaches sell it, and that a strong enough reason makes it mostly unnecessary. I agreed with part of that. My word for it is awareness over discipline. Discipline can point at the wrong thing for a very long time, and I know people who are extremely disciplined in the gym and use it to run from their relationships and their finances. I was one of them for a while.

What's your definition of a successful human?

Andy asks every guest this, and his own version has four parts: success, connection, influence and happiness, each needing the others to last. My answer on the day was that a successful human is someone who feels fulfilled in every core area of their life. That means fulfilment in their work, which doesn't have to be entrepreneurship and could just as well be a career. It means fulfilment in their body and health, being happy with what they see in the mirror and still striving for something. It means a few solid relationships, a supportive partner and kids if you're at that stage. And it means enough money to do whatever you're being called to do. You don't have to be Elon Musk.

Then Andy asked what defines those core areas, and I told him that was a bit deep and I might need to lie down.

My honest answer is that there's no framework or pillar system other than the one that's unique to you. I keep coming back to a growth-in-unison mindset, where you grow across the areas of your life together rather than pouring everything into one. I also have someone close to me who's well off, has a great mind and a strong connection to his faith, and struggles with his fitness. By his own definition he's fulfilled, and he's still chipping away at it. If a person can say what success means to them, they've more or less defined their own core areas.

It's worth noticing that I defined success as fulfilment and not as achievement. It's possible to hit every target on the list and still not feel fulfilled, and the two come apart more often than people expect. I'd rather aim at the one that's actually worth wanting.

How do you stay adaptive without losing focus?

It's a paradox, like most things. I try to ask enough questions to find where someone's potential is and where they're being drawn: what comes naturally, what they've done before, where the leverage is, what they're passionate about. That gives an educated guess at a direction. Once you have one, you need structure to execute it. I'm spontaneous by default, so I have other people hold me accountable to the steps.

Data, intuition and the live stream of now

Andy's view was that data gives you clues rather than answers, because it's always the rear-view mirror. I agree, and as data-driven as I am, my core is intuition.

The way I think about it is that life is happening now, and by the time I've said the word it's already three seconds ago. There's an ever-present moment that follows us into every next moment, and I picture it as a live stream. If you can still your mind enough, slow your nervous system and find some flow, you can start to tap into it. That's a muscle of awareness, and it can be trained. Data is the pattern of the past, and the live stream is what's happening now.

When the noise gets too loud, even the well-meant noise of advisors, mentors and the people closest to me, I need to still myself before anything gets through. For me that's a whiteboard with some jazz on and the lights low, moving around, sometimes shadow boxing. A clear direction tends to come out of it, and it doesn't rely on the numbers.

Why do people stay in scarcity, even when they're doing well?

Andy put a good question to me here. Some people sit in a scarcity mindset while being numerically better off than others, and still end up feeling like they have a worse life. Others have little money and feel enriched. Why?

I gave him two answers. The first is the old line that change happens when the pain of staying the same becomes greater than the pain of changing. For a lot of people the pain of change is bigger, so they stay, and some stay for a lifetime. The second is familiarity. If all you've known is scarcity, any other way of thinking can trigger the hell out of you. It's a paradigm breaker, and it can feel like an identity crisis.

Andy pushed back on the first one, and fairly: scarcity is already painful, so the pain of change can't fully explain why people don't leave it. I gave him that. Where we landed was identity. Scarcity is conditioning, and conditioning is what we're fed by society and media. You can't change it if you aren't aware of it, or aware of the identity it's shaping. So the work is to notice how you've been conditioned, decide how you want to be conditioned, and then control your environment accordingly, even when it hurts. I think of it as designing a version of yourself and moving toward it over five or ten years.

I see a version of this in my own work. I can often spot what someone is sitting on in their business or brand, a pot of gold they haven't noticed, and when I do I'll tell them and offer to help, even if it's only an introduction. Sometimes the response is that they've been trying to work this out for months. Other times the idea is so far from what they're used to that it intimidates them, and all I get is a double tap or a "thanks so much, maybe one day." Scarcity doesn't see the abundance that's already there.

Are phones taking our identity?

Andy is about to swap his smartphone for a basic phone and measure what changes. I told him his thesis is right, and that the technology isn't going away. I decided to stay at the frontier of it and keep my own awareness, so I can talk to the next generation about it. Every profile is a channel, and the risk is when you start identifying with the channel. If your mood follows your engagement, that's an attention score, and you should treat it as one.

When did you lose awareness of who you were?

I went back to my twenties and early thirties, when I reached the lifestyle I'd been chasing and felt exactly the same as before. Achievement and fulfilment turned out to be two separate things, and I'd only been working on one of them.

What's the one thing you need to improve?

Asking for help. I've spent most of my career being the person others come to. I'm growing a company further than I ever have, and I'm managing money at a scale that's new to me. Everyone who could help is within reach, and I have to get past the idea that I should already be able to carry it myself.

What I took from the conversation

• Define fulfilment on your own terms. A borrowed framework will have you optimising for someone else's picture of success, and fulfilment tends to need more than one area of life working.
• Check what your discipline is for. It's valuable, and it can also keep you from looking at the part of your life that isn't working.
• Stay adaptive, then add structure. Find the direction by asking good questions, then build the rigidity needed to execute it.
• Use data for clues and stay present for the rest. Data describes the past. I need quiet, a whiteboard and some space to hear what's actually in front of me.
• Respect how strong familiarity is. What you know can keep you where you are long after it stops serving you, and you can't change conditioning you can't see.
• Be careful what you attach your identity to. That includes metrics, attention and the channel you've built.
• Ask for help earlier than feels comfortable. It's the thing I still have to practise.

A thank you to Andy

Andy, thank you for the questions, for the pushback where you gave it, and for a conversation that didn't stick to the format. It was a pleasure, and I'd happily have more conversations like this.

Where this goes next

That last point comes up with almost every founder I work with. Most of us are very good at carrying things, and it takes someone close enough to see what we can't before we notice where it's costing us. That closeness is what the Founder Accelerator is built around.

If you'd rather hear the conversation than read it, the full episode is on Spotify.