I talked with Holly Gutwillinger about finding your way into writing, and what it takes to start seeing yourself as a writer before you necessarily feel like one.

We talked about inner critics, looking for validation, going back to school for writing, learning to trust your own voice, and what happens when creative ambitions start turning into pressure. We also got into writing on Substack, receiving criticism, trying to keep creativity enjoyable, and giving yourself some room when schedules and expectations become too rigid.

And because Holly’s dogs have played such a big part in her creative life, we talked about them too: how they inspired her first book, her podcast, and the stories she is still writing now.

Teresa and I started with a question: what happens when something that once helped us starts getting in the way?

From there, we ended up talking about the identities we build around old ways of coping, why they can be difficult to let go of, and whether what we often call “self-sabotage” might deserve a little more curiosity.

We talked about people-pleasing, gaming, boundaries, changing habits, the different versions of ourselves we bring into different parts of life, and what it means to choose something different when other people have become used to who we were before.

Teresa also shared the story of moving her family from Rome to Saudi Arabia after a difficult few years, and what made them keep pursuing that possibility even when the original plan fell apart.

We finished with a question I think captures a lot of the conversation:

What is this old habit still doing for me?

I sat down with Peter Ashby-Smith, who writes The Stoic Futurist, for a conversation about what it means to live and work in a world that seems to keep changing faster.

We started with our own somewhat overlapping paths through careers, entrepreneurship, higher education and writing, including Peter’s move towards a portfolio career and my own attempt to figure out what comes after building and exiting a company.

From there, we ended up talking about quite a lot: whether being a generalist can actually be a form of expertise, why AI sounds authoritative even when it is wrong, what parts of our thinking we should and shouldn’t outsource, and how ancient Stoic ideas might still be useful when dealing with very modern problems.

We also got into the “crisis competence trap”: what happens when being good in a crisis becomes part of how we measure competence, and whether constant busyness can quietly become something we start valuing for its own sake.

That led into work, presence, the difference between work-life balance and work-life integration, and why having some control over when to push hard might matter more than simply working less.

We finished by talking about agency and perspective. Peter brought up the Stoic practice of looking at your life from above, creating some distance between yourself and whatever problem currently feels enormous. I shared an experience from my own life that helped me learn something similar.

Thank you Peter for the thoughtful conversation.

Rough chapters

00:00 — Meet Danielle Wright and Your Next SprintDanielle’s recent rebrand, motherhood, project management background, and her discovery of Substack.

03:00 — What Agile looks like outside software developmentSprints, backlogs, capacity, choosing what matters, and breaking large ideas into useful smaller steps.

08:40 — Bringing Agile thinking into real lifeDan’s software background, Waterfall vs. Agile, and why plans need room to change.

13:30 — The messy middle is more interesting than polished successDanielle’s Sprint Showcase idea, showing unfinished work, and the discomfort of putting something imperfect in public.

16:20 — Do we actually want feedback, or reassurance?Critical feedback, coaching groups, getting uncomfortable input, and learning from other writers.

20:20 — Learning to write by publishingSubstack growth, unpredictable reactions, improving as a writer.

23:50 — Using AI without losing the person doing the writingAI for planning, drafting and structure, AI detectors, trust and voice.

32:00 — Creating alongside work, family, and everything elseDanielle’s young family, planning life with limited time, experimenting with systems, and using what works without insisting everyone needs the same system.

38:00 — Does your framework need to become your identity?The difference between using Agile internally and making it the public-facing brand.

42:15 — Niches, ideal readers, and figuring out who you write forDanielle beginning with moms, Dan deliberately writing more broadly, natural subscriber churn, and allowing the audience to sort itself out.

47:00 — Closing thoughts: small steps and having optionsDanielle’s suggestion for overwhelmed creators, Dan’s closing thought about the options available to us.

I sat down with Re1nGer, writer of The Liberation Project, for a conversation about some of the questions neither of us is interested in answering too quickly.

We started with meaning and purpose. Is purpose something we find, something we create, or something life sometimes chooses for us?

From there, we wandered into the different versions of ourselves we show other people, how much of our desires and thoughts are actually our own, what we’re both trying to do through our writing, and why finding a way to write that feels like yours can take a surprisingly long time.

We also had plenty of questions from people watching live, which took the conversation in a few directions neither of us had planned.

Eventually, the conversation took an unplanned turn into AI, software development, and what might happen when a useful tool makes it increasingly tempting to outsource not only work, but thinking itself.

Somewhere underneath all of it was a question we kept returning to in different forms:

How much of the life we’re living did we actually choose?

Rough chapter list:

00:00 — Introductions: Creative Living and The Adaptive Human

02:00 — When Doing Too Much Turns Into Burnout

04:04 — Learning to Say No and Making Space for Yourself

06:31 — Finding Time to Create in a Full Life

10:33 — Working With Interruptions Instead of Against Them

11:49 — Balancing Writing, Work, School, and Everything Else

15:53 — Rituals, Music, and Getting Into Creative Mode

18:01 — Why Have a Creative Life at All?

22:36 — Books, Ideas, and Where Creativity Comes From

25:36 — Flow, Marinating, and Different Creative Processes

29:00 — When Life Refuses to Follow the Plan

32:34 — Energy, Family, and Knowing When You Need Space

37:28 — Creating When You Don’t Have Much Energy

40:34 — Modern Convenience, Complicated Humans, and Emotional Signals

44:44 — Creativity as a Way of Staying Awake to Your Life

48:21 — Making Home a Place That Supports Your Life

54:01 — Personal Growth, Reading, and Learning From Other People

56:18 — Closing: Small Experiments and Moving Toward the Horizon

00:00 – Introductions: The Adaptive Human and Creative on PurposeDan and Scott introduce their publications and the ideas behind their work.

01:05 – Doing the Work You Have to Do While Building the Work You WantMaking space for meaningful work without prematurely abandoning financial responsibilities or burning bridges.

03:30 – There Is No Final DestinationHow previous roles continue to support what comes next, and why every finish line becomes another starting line.

06:35 – When Success Looks Right but Feels HollowScott introduces the “zest barometer” and the distinction between doing the wrong thing and doing the right thing in the wrong way.

10:20 – Scott’s Career Transitions and Building BridgesScott reflects on moving from teaching to music, guitar instruction, writing, and helping others realize their potential.

13:15 – Dan’s Experience of Stepping Down as CEODan tells the story of founding his company, leaving the CEO role, becoming a developer again, and questioning whether the decision was personally right.

18:05 – Decisions, Outcomes, and the Identity TrapWhy good decisions can produce bad outcomes, and how other people’s view of our identity can keep us inside roles that no longer fit.

21:05 – What Actually Changes Behaviour?Becoming something by doing it, the dangers of being dull, distracted, or delusional, and taking responsibility for what remains within our control.

25:00 – Stoicism as an Operating System for LifeScott discusses Marcus Aurelius, Stoic philosophy, and the principles behind his upcoming book.

26:40 – Dan’s Philosophy: Presence, Trust, and RecognitionDan reflects on The Power of Now, trusting that life has a way of working out, and the formative experience that taught him to see his life from outside himself.

31:15 – Emotions, Awareness, and the Pause Before ResponseHow emotions become harmful when we cling to them or react too quickly, and why recognition often requires another person holding up a mirror.

34:00 – Why More Tools Usually Aren’t the AnswerCommunity, clarity, subtraction, and why courses, software, tactics, and masterminds can become substitutes for confronting the actual problem.

36:20 – The Appeal and Limitations of ShortcutsWhy other people’s systems often fail to transfer, and the difference between enduring principles and strategies built for someone else’s circumstances.

39:00 – Looking Inward Instead of Writing Another GuideDan explains why he resisted turning recognition into a universal model, and why people may already know more about their next step than they admit.

41:10 – Does Meaningful Work Need to Make Money?The difference between earning a living and living meaningfully, including dreams and interests that may not need to be monetized.

42:55 – No Philosophy Has All the AnswersThe shared ideas beneath Stoicism, Buddhism, Christianity, Eckhart Tolle, and other traditions, without turning any one of them into an identity.

47:15 – Humour, Stress, and the Game of LifeDan reflects on laughter as both optimism and a response to uncertainty.

48:00 – Learning Through ConversationDan and Scott discuss live conversations as a way of refining ideas, expressing them more naturally, and changing their minds.

49:30 – Closing: You Can’t Win a Game You Don’t Want to PlayScott’s final reflection on deciding what matters, defining the gap, avoiding distraction, and enjoying the process.

In this episode of Behind The Adaptive Human, I talk about two essays from this week, a live conversation with Ryan Maxwell, and several experiments I'm currently running inside the publication.

Topics discussed:

• The idea behind At Some Point, I Became Someone Who Was Always Working on Himself• My conversation with Ryan Maxwell• How that conversation led directly to The Gap Isn't Always the Problem• Recognition poems and why I'm experimenting with them• Restacking other writers more intentionally• A preview of Sunday's upcoming essay• Why I'm retiring the old podcast format• The future of Behind The Adaptive Human• The return of Wednesday reflections

This episode is also a reflection on something I've been noticing more and more:

The publication is growing, but so am I.

Part of building The Adaptive Human is learning how to share ideas publicly, experiment in real time, and follow the topics that feel most alive when they appear.

Referenced:• At Some Point, I Became Someone Who Was Always Working on Himself• The Gap Isn't Always the Problem• Ryan Maxwell's publication, Chasing Maximus

Ryan Maxwell and I discuss adaptation, identity, drift, and the gap between the life we've built and the life we crave.

Discussed topics:

1 min – Introductions & Backgrounds7 min – The Origins of The Adaptive Human9 min – Why Adaptation Became the Central Theme13 min – When a Life That Works Stops Feeling Like Yours17 min – Direction vs Destination21 min – Listening to Yourself29 min – The Gap Between the Life We’ve Built and the Life We Crave31 min – Ryan’s Framework: Drift, Notice, Return37 min – How Do We Know Which Gaps Matter?40 min – Emotional Triggers, Blind Spots & Protection Mechanisms46 min – Conflict, Relationships & Emotional Withdrawal52 min – Closing Thoughts

Why I Write The Adaptive Human

In this episode, I share a bit of my own story and try to explain why I started both The Adaptive Human.

For a long time, I thought my challenge was figuring out what I wanted from life. Looking back, I think the deeper challenge was learning how to see what was actually happening inside me.

We talk about adaptation, identity, careers that look right on paper, and the difficulty of putting certain experiences into words while we're still living through them.

I also share why I started this podcast, how it differs from my essays, and what I hope to explore in future episodes.

Topics discussed:

- Adapting to life's different stages and roles- Feeling disconnected despite outward success- Why some experiences are difficult to name- The origins of The Adaptive Human- Why I started a podcast alongside my writing- Recognition, uncertainty, and understanding ourselves

If you're new here, this is a good place to start.

If something here feels familiar, you'll probably find more of it in the essays. New pieces arrive every Wednesday and Sunday.