𝗧𝗿𝗮𝗻𝘀𝗳𝗼𝗿𝗺𝗮𝘁𝗶𝘃𝗲 𝗚𝗿𝗼𝘄𝘁𝗵 𝗖𝗼𝗮𝗰𝗵𝗶𝗻𝗴 𝗳𝗼𝗿 𝗙𝗶𝗿𝘀𝘁-𝗧𝗶𝗺𝗲 𝗙𝗼𝘂𝗻𝗱𝗲𝗿𝘀
It’s not just about scaling your business.
It’s also about scaling you.
From Fortune 500 companies to fast-growing startups, I’ve coached leaders at every stage. Today, my mission is focused: helping first-time founders scale themselves as fast as they scale their companies.
 
𝗠𝘆 𝗙𝗼𝗰𝘂𝘀
Your startup can only grow as fast as you do. As a first-time founder, you’re under pressure from investors, your team, and your family—all while learning on the fly skills that others spend decades mastering. Whether you’re raising capital, hiring your first team, or pushing toward product-market fit, I help you close the gap between where you are and where your company needs you to be.
 
𝗪𝗵𝘆 𝗠𝘆 𝗔𝗽𝗽𝗿𝗼𝗮𝗰𝗵 𝗪𝗼𝗿𝗸𝘀
I bring 20+ years of coaching 10,000+ leaders, founder experience, and cutting-edge insights from neuroscience and behavioral psychology. The result: a proven path to accelerate both personal and company growth. My frameworks help you:
• Transform self-doubt into clarity and influence
• Build and inspire high-performing, durable teams
• Raise capital while staying true to your vision
• Create sustainable success without burnout
• Leverage your existing strengths while closing critical skill gaps
• Grow yourself as fast as your company 
 
𝗪𝗵𝗼 𝗜 𝗦𝗲𝗿𝘃𝗲
My one-on-one clients are founders who:
• Want tailored, responsive coaching that meets them where they are
• Care deeply about building strong teams and cultures
• Aim to create both impact and enterprise value
• Refuse to accept that success means sacrificing their families, health, or lives outside the company
• Are willing to grow personally and professionally to become the leader their company needs 
 
𝗥𝗲𝗮𝗹 𝗜𝗺𝗽𝗮𝗰𝘁
From doubling revenue to unlocking fundraising rounds to transforming team dynamics, my clients consistently achieve breakthrough results—while building lives they actually want to live.
 
𝗪𝗮𝗻𝘁 𝘁𝗼 𝗖𝗼𝗻𝗻𝗲𝗰𝘁?
Visit www.andrewpoles.com/contact or DM me here.

Andrew Poles

This is one of those leadership truths that sounds simple and may take years to embody. Early on, being the hero feels like care, competence, and responsibility. Over time, it quietly becomes a ceiling. 
The real work is shifting from proving your value to building others’ capacity and confidence. 
When people grow stronger around you, leadership stops being exhausting and starts being expansive.

Coaching first-time founders to grow themselves and their companies | 3x Founder | 22+ years coaching partners like NASA, Dell, Schwab + 10,000 people worldwide

Your success, my mission | CEO @ Polished Carbon | Former CIO $4B company | DEIB ally | Sharing 25 years of hard-won wisdom on people-first leadership + emotional intelligence + self-mastery

Leadership isn't about being the hero.

It's about creating heroes.

You don't earn your team's respect by showing off
your superpowers.

You earn it by helping them discover their own.

Because true leadership is seeing potential
in someone before they see it in themselves.

Then showing them how to unlock it.

It's not about:
➟ Being the smartest in the room
➟ Solving all the problems
➟ Having every answer

It's about:
➟ Asking the right questions
➟ Drawing out hidden talents
➟ Building confidence in others

Your legacy isn't measured by your achievements.

It's measured by the people who grew
stronger under your guidance.

Remember:

Great leaders don't create followers.
They create more leaders.

That's the privilege of leadership.
That's the responsibility.
That's the gift.

Your superpower isn't what you can do.

It's what you help others become.

♻️ Agree? Repost to share with your network.
🔖 Follow Justin Wright for more on leadership.

You and me against the problem - never you against me, or me against you.

That is a key shift that allows for productive disagreement between cofounders.

How many times do we find ourselves at odds over some issue or decision with someone with whom we share decision making or execution responsibility, and then quickly, the disagreement over the issue becomes a break in the relationship inside of which we're attempting to work out the issue? 

What I find works is to practice - it's always you and me against the challenge. Never one of us against the other. 

In marriages. In co-founder dynamics. In Board meetings. On teams.

You & Me. 

Check out the full interview. Link in the comments.

It was great to be interviewed on The Secrets of the High-Demand Coach podcast with Scott Ritzheimer. 

We dove deeply into the issues of co-founder tension, how to run a business when you disagree, covering situations where one co-founder has more legal control than the other as well as situations where control is shared and decisions must be agreed upon. 

Having seen several co-founder relationships blow up unnecessarily over challenges of disagreement, I know how challenging this topic can be to navigate. 

I’d really love if you gave this episode a listen.

Open article: Podcast Template with Scott Ritzheimer – Ep. 0–duplicate-1 by scalearchitects.com

Podcast Template with Scott Ritzheimer – Ep. 0–duplicate-1

Who knew we could learn so much from trees about how to build powerful companies?

In this interview with Scott Ritzheimer of the Start, Scale and Succeed Podcast, we explore the intricacies of co-founder dynamics and how to successfully navigate some of their thornier aspects.

Part of our discussion centered on what I feel is a hidden secret to greasing the gears of performance - human connection.

Do you tend to the quality of your connections with the people you partner with and lead? 

If not, you might want to reconsider. 

For the full interview, see link in the comments below.

Most founders I work with are running on a fuel they never question: chronic dissatisfaction.

It drives results–but it also quietly burns you.

This article introduces a different fuel for elite performance–one that keeps your edge without costing you your health, relationships, or joy. 

If you’ve ever felt afraid to slow down or feel “good enough,” this is for you.

Most leaders I work with are driven by a deep, often unspoken fear: If I let myself feel satisfied, I’ll lose my edge. We’ll stop pushing. There will 

Open article: And Why “Satisfaction” Isn’t the Answer Either by Andrew Poles • 4 min read

And Why “Satisfaction” Isn’t the Answer Either

The holidays are supposed to feel whole.
But for a lot of leaders, they don’t.

Old tensions with teammates.
Unspoken resentment with a cofounder.
Judgment you’re still holding against yourself for a decision that didn’t work.

This issue isn’t about being “nice.”
It’s about forgiveness as a leadership skill–and why it might be the thing that restores trust, clarity, and momentum in your company heading into the new year.

If relationships at work feel heavier than they should this holiday season, this is for you.

The word holiday comes from holy day. And before “holy” was a religious word, it meant something simpler—and deeper: set apart, venerated, whole, unbr

Open article: The thing that actually nourishes collaboration gets buried under performance, pressure, and expectations. by Andrew Poles • 4 min read

The thing that actually nourishes collaboration gets buried under performance, pressure, and expectations.

This proverb keeps coming back to me.
Not because it dismisses sorrow - but because it draws a clean line between *experiencing* it and *living inside* it.
We don’t get to control the thoughts or emotions that pass through on a hard day.
We DO get to choose whether we let them take up residence and start shaping our identity, our decisions, or our future.
That small pause - one breath, one reset - is often the difference between wisdom and rumination.
And over time, those pauses compound.

NYT Bestselling Author | Entrepreneur | Investor

This proverb lives rent-free in my head.

(read it once and you'll see why):

"You cannot prevent the birds of sorrow from flying over your head, but you can prevent them from building nests in your hair." - Chinese Proverb

If you attach yourself to the sorrow, continue to think all of the negative thoughts it brought about, repeat the patterns of your past, dwell in the pain, and bemoan your bad luck, you allow the nest to be built.

If you pause, breathe, give yourself a moment to reset, and choose a balanced response, you send the birds flying off into the distance.

The choice is yours…

—

♻ Repost to remind someone: don’t let sorrow build a nest.
🔔 Follow Sahil Bloom for more life wisdom like this.

—

📌 Want 50 simple rules for living calmer and clearer?

Download my Most Powerful Life Hacks PDF (free) and join 800,000+ who get my newsletter: https://lnkd.in/edxXi82t

This is a solid reminder that momentum doesn’t come from hype - it comes from clarity. 
Looking back honestly isn’t about judgment; it’s about separating what actually worked from what just kept you busy. 
The quality of 2026 will be shaped less by new goals and more by how cleanly you integrate the lessons from 2025. Reflection done this way becomes a strategic advantage, not a sentimental exercise.

Founder at Bloomful | Helping founders and execs build a credible LinkedIn presence | Keynote Speaker, Medical Doctor, Ex-BCG

Your strongest 2026 starts with a brutally honest look at 2025.

Growth always demands reflection.

Future successes depends on the questions you ask today.

7 powerful questions to supercharge your 2026:

1. Where did you show resilience this year?
↳ When did you prove your strength or resilience?
↳ Use resilience to tackle bigger challenges in 2026.

2. Who supported your growth this year?
↳ Who made a real difference to your growth?
↳ Invest in meaningful relationships to fuel success.

3. What fears held you back this year?
↳ What stopped you from acting on what mattered?
↳ Stop avoiding fears; face them head-on instead.

4. Where did you excel & create impact?
↳ What moments made you feel proud of your work?
↳ Lean into strengths to have bigger impact in 2026.

5. What brought you the most joy this year?
↳ What moments or people made you happiest?
↳ Prioritise what lights you up to build a fulfilling '26.

6. What would you do differently in 2026?
↳ What choices would you approach differently?
↳ Turn the lessons into a smart strategy for next year.

7. What vision will guide you into 2026?
↳ What inspires you when you imagine life in a year?
↳ Let a clear, bold vision drive your decision making.

As the year wraps up, taking time to reflect
Helps set the stage for a successful 2026.

What’s your top tip for reflecting on the year?
Let me know in the comments below👇

📌 If you like this content, you might like my free newsletter—sign up here: https://lnkd.in/ekfMRpWJ

♻️ Repost to help others plan their best year yet.
➕ Follow Dr. Dupe Burgess for more.

7 Powerful Questions To Supercharge Your 2026

What's the answer to unequal co-founder, or decision maker, authority?

What do you do when one co-founder will have the ability to overrule the decision in nearly every case? Is that a workable situation?

That depends, but the work of determining if this can be a workable agreement mostly falls on the co-founder or decision maker who is ceding authority to their partner.

It can work if the right work gets done IN ADVANCE.

Otherwise, I've seen this situation broil, and turn into co-founder resentments that can cost you the company.

For a full discussion on how to navigate co-founder tension, see the full interview with Scott Ritzheimer on his podcast Start, Scale and Succeed. 

Link in comments below.

Exited founder turned CEO-coach | Helping founders discover who they are as leaders and build high-performance, low-drama companies

Over 15 years I founded and served as CEO to three VC backed companies (one big exit and two learning experiences), all while presenting only the most polished, hyper-competent version of myself and my company, at all times. And then, in 2020 I left it all behind.When I signed the papers, officially removing myself as CEO of the company I’d started a decade prior, it felt like I’d been punched in the gut.Without my persona as the “CEO of VNN,” I realized that I had no idea who I was anymore, or what to do with my life.It was the opportunity of a lifetime.I spent the next 2 years searching, meditating, hanging out with monks, diving into psychedelics, and trying on new identities that never felt right.I was stuck.And then, I finally opened up.I started being honest about my struggles, despite the voice in my head telling me to play a role. I let go of my compulsion to be “Ryan the CEO,” or “Ryan the entrepreneur,” or even “Ryan the guy who’s raised a ton of money and scaled a media company.”I was just, Ryan.And the most surprising things happened.1. The more I opened up, the more everyone else did around me. My network grew and developed into one of deep relationships spanning life and business.2. The more I let go, the more the universe seemed to place exactly what I needed on my doorstep. Things began to happen organically, in ways much better than I could have planned.3. The quieter my mind got, the more I was able to access an innate wellspring of creativity and inspiration that, frankly, made work feel easy and joyful.Me, the guy who’d worked so hard his whole life to be perfect, when I learned to let go and be me, great, meaningful work flowed out of me.And from that foundation, I started Inside-Out Leadership, a boutique executive coaching firm that helps founders transform their companies into their masterpieces and step fully into their lives.Today, in my work as a coach I see the tendency to present that veneer of polished competence in nearly every founder I meet. And while I recognize the need for presentation in some cases (fundraising, recruiting), I also see how that need to look good actually gets in the way of our learning and growth.If you're tired of doing your own impression of the "perfect leader," you're not alone.Shoot me a DM. There's another way. And it's fucking incredible.

Ryan H. Vaughn

Once upon a time, I won $500k from a five-minute business pitch, but I still think the business pitch, as currently constructed, is leading investors to fund the wrong entrepreneurs...

I have a friend. Immigrated from a war zone in Haiti with his family. Served in the military with distinction. After becoming a civilian, he founded multiple businesses, including a few aimed at helping vets. I have some high-capacity friends, but this particular friend is a force of nature.

I got to witness him pitch to a couple of angels & seed investors a while back. 

He told his story, explained what he was raising money for, but even as he was pitching, I found myself getting confused. The pitch didn’t follow the format I’m used to, and as a result, it wasn't as clear as it could have been. I noticed this, so I wasn’t surprised when the investors told him he was too early. 

These investors, who will tell you until they’re blue in the face that at the seed stage they bet on the jockey and not the horse, unceremoniously turned down a force of nature because his pitch didn’t match the pattern they’re looking for. 

And it got me wondering: is the investor pitch really the best way to make an investment decision at the seed stage? 

If it really is about the jockey, and not the horse, shouldn’t our attention be on learning about the jockey?

Now I get it. A good presentation at the seed stage is indicative of someone who will be able to give a good presentation at later stages. This is important.

But this is also a learned skill. 

There is a “right way” to present your business, which I or any other experienced fundraiser could teach a young entrepreneur in an afternoon. It’s glorified paint-by-numbers.

At the seed stage, having a great pitch is compelling. But however compelling it sounds, the business is wrong. 

It’ll change a ton of times between then and any sort of exit, so having a good pitch really only proves that you know the combination lock to get investors excited. 

Instead, we should be looking for someone who can create their own path when there is no clear way forward. 

What if, instead of focusing our diligence on the fundamentals of a business that will change umpteen times, we asked entrepreneurs to tell their stories? 
What if we tailored the process to finding the best jockeys, knowing that we can train them to pitch to later-stage investors as we go?

The best entrepreneurs, invariably, have incredible stories from their lives, school, the military, previous companies, etc. Stories of amazing resilience in which they've overcome incredible odds. Learning about how a person has navigated these environments in their past will tell us more about their ability to do those same things than asking them to make up pretty-sounding shit.

If what we’re really looking for at the seed stage is good people, shouldn’t we design our vetting process around figuring out who it is, really, that is pitching us?

I'd love to hear your thoughts below.

Exited founder turned CEO-coach | Helped early/mid stage startup founders raise over $500m, and create equity value over $12bn (and counting...)

No alternative text description for this image

Jim Carrey stood on the Golden Globes stage, a two-time winner, looking out at a room full of the most successful people on earth. What he said next is a valuable lesson to us all: 

“I am two-time Golden Globe winner Jim Carrey...
And when I dream, I don’t just dream any old dreams. No sir. I dream about being three-time Golden Globe winner Jim Carrey. 
Because then I would be enough. 
It would finally be true. 
And I could stop this, this terrible search. 
For what I know, ultimately won’t fulfil me.”

He was joking, but at the same time, he definitely wasn't.

This is the sacred, self-inflicted wound that drives every high-achiever.

It starts with a dream. And with the first whisps of the dream, the machine locks in, and the outcome is set.

You create details, bringing the dream to life. And the minute it's real, a tension is born: a taut rubber band stretching between the dream and you. 

The dream is always pulling. 

You feel this tension as the disappointing, unself-actualized side of yourself, which compels you to chase, to change today to conform to your vision for tomorrow. This tension propels you out of bed every day.

We deify this tension as ambition. We call it "making something of yourself." But in addition to propelling us, it permeates life with a generalized dissatisfaction that no amount of achievement can solve. The moment you attain a piece of your dream, it becomes irrelevant, overwhelmed by the necessity of attaining the next piece. If you attain the whole thing, your dream will have receded, sitting as far out of reach from your hard-won perch as it was at the start.

The bargain is this: to succeed in getting closer to my dream, I offer in trade my contentment, in full, and vow to never be satisfied. 

This is the trade many high-achievers make. They get the allure of the chase at the cost of the moment.

Chasing a dream translates roughly to "wishing things were different from what they are." Since they cannot possibly be, our perpetually unfulfilled wishes leave us wanting. The game of chasing an ever-receding mirage is a game you can't win. 

I see this most often with founders right after an exit, to whom I say:

If you can still convince yourself that building a bigger company will finally make you feel complete - considering the last exit didn't - then do it. It is by far the easier path. 

It’s just like Jim Carrey's "dream" of a third Golden Globe. 

But eventually, you realize that no exit is big enough to make you feel whole in a lasting way. 

That is the moment the real work begins. The work that leads you away from chasing achievements to feel complete, and into the actual work of your life.

That transition - from performer to person - is the most exciting part of what I do.

It’s when you finally stop searching. And start living.

---

Proud to coach with Inside-Out Leadership, CEO coaching by exited founders who've been there.

Somewhere along the way, many of us lose the ability to pretend.

We stop softening our words.
We stop managing the room.
We stop spending energy trying to be palatable.

What once felt automatic starts to feel exhausting. And then, quietly, it stops working.

This is not bitterness. And it is not a personality flaw.

There is actually some interesting science behind it.

I recently read an article by Ellen Scherr that explored how, as we age, the brain reorganizes itself. Neural pathways tied to constant social monitoring and emotional labor get pruned. Energy becomes more precious. And the brain becomes less invested in managing how we are perceived. 

In simple terms, we become less compelled to please.

The article talks about women in particular, but I see this shift in the men I work with all the time. Founders in their 40s and 50s become more direct. They people-please less. They stop contorting themselves to fit rooms they have already outgrown.

And almost without exception, life feels more intense: More alive, Less numb.

Usually, they often become more effective too, because they are no longer self-limiting just to fit in.

A lot of my clients come to me wanting to trust themselves more and show up as more thoroughly themselves, with fewer filters in their lives.

That transition matters.

When people let go of those filters, everything sharpens. And in our work, we help people get to know themselves deeply enough to trust what wants to come through.

But there's another way this happens: Age

I see it in most clients as they grow older. They care less about what they used to care about, especially socially. They become more direct. They give less fucks.

There are ways to accelerate that. Inner work is one of them. But age is a very reliable indicator. Think of your nana, farting loudly in the middle of dinner and completely ignoring it. It's that sort of thing.

Now, you may not want to go around farting everywhere.

But letting go of all the subtle ways you limit yourself to fit in is, in my experience, unquestionably a happiness and effectiveness amplifier. 

When you stop checking whether you're acceptable and adjusting yourself in real time, you stop outsourcing your authority to the room.

This is not about becoming careless or abrasive. There's a difference between authenticity and unintegrated impulse. It's about reclaiming parts of yourself that were kept hidden primarily to keep the peace.

Age will eventually take you there. Inner work can take you there sooner.

Either way, the destination is the same.

 A life that feels less managed. Less split. More honest.

If this feels familiar, nothing has gone wrong. You may just be growing into yourself.

And that is not something to fix.

-

Proud to coach with Inside-Out Leadership, CEO coaching by exited founders who've been there.

Step 2, The Eulogy: Imagine that you are at the end of a long, rich life. You’ve accomplished everything you wanted, behaving honorably and building meaningful connections with your family, friends, and colleagues....

You are proud of yourself for leaving a great legacy and for having led an organization that brought great value to the world.

You’ve done your work here and feel ready to go. 

So when you learn that your days are numbered, you take the news in stride. A lot of people who appreciate and admire you want to pay their respects, so they organize a “living funeral." At the ceremony, a dear friend will stand in front of the audience and read a eulogy.

Here is your instruction:

Spend at least 20 minutes and write the eulogy you would like your friend to give.

Please don't be humble or shortchange yourself by limiting this in any way. If it's possible for anyone, it's possible for you, and you only get this one shot. This kind of eulogy can become a north star for your life. It can help you discover who you want to be and how you want to act in order to feel complete when you leave your life.

Once you're done writing your eulogy, you're done with this step.

Pro tip: Don’t allow yourself to edit; just let yourself flow in a steady stream of consciousness.

The reason most people get stuck doing deep writing like this is that two competing energies lock horns: the Madman and the Judge.

The Madman is the raw, creative energy inside you. He’s full of ideas and writes crazily, driven by pure emotion. But the Judge - that critical, educated voice of perfection - peers over your shoulder and says, "That's trash!" The Madman loses confidence, shrivels up, and the writing stops.

If you want the truth of your deepest purpose to emerge, you have to separate these energies:

The Madman must be allowed to speak freely, without editing or censoring, for the full 20 minutes. He doesn't worry about punctuation or grammar. He just writes.

For this exercise, your job is to bypass the internal critic and allow your deepest, non-performative truth to flow onto the page. The judge can come in after the 20 minutes are up to fix the errors (or he can take a break from this exercise entirely).

Let your legacy define your actions. What are the truths about your character you want to be read from the podium?

The biggest risk to your life is not failure, but the quiet compromise of your own truth. 

Follow along for the next five days as we continue the reflection sequence. 

And, if you'd like access to the full Annual Reflection Template, comment "Gimme gimme" below.

Exited founder turned CEO-coach | Helping early/mid-stage startup founders scale into executive leaders & build low-drama companies

Anxiety is the price of the life you were meant to live. James Hollis said that years ago, and I’ve found it to be painfully accurate.

If you’re building something new, stretching beyond who you’ve been, anxiety is inevitable. 

Not as a flaw. As a signal.

Most people treat anxiety like an enemy. Something to suppress, outrun, or eliminate. And when that doesn’t work, they assume something is wrong with them.

Usually, nothing is wrong.

Anxiety is your nervous system doing its job. It’s an alarm designed to pull your attention toward something that matters.

The problem isn’t anxiety. It’s our relationship to it.

When you resist anxiety, it tightens.
When you try to override it with logic, it gets louder.
When you numb it, you mute everything else too.

What actually helps is learning to interpret it.

Some anxiety is functional. It’s telling you to act. Make the call. Fix the problem. Adjust the plan. Once you do, it quiets down. Feature, not bug.

Other anxiety is patterned. Old. Installed early. Designed to protect you from hurts that are no longer present. That kind of anxiety doesn’t resolve through action. It resolves through feeling it fully. Listening to it all the way, until it has nothing more to say.

That’s the part most people avoid.

Because feeling anxiety fully takes courage. It requires slowing down instead of muscling through. Listening instead of fixing. Trusting that the emotion isn’t here to destroy you, but to show you something.

When you learn to work with anxiety this way, it stops running your life from the background. It becomes guidance instead of interference.

The irony is that the leaders who feel the most alive, most grounded, most effective aren’t the ones without anxiety.

They’re the ones who stopped fighting it.

---

Proud to coach with Inside-Out Leadership , CEO coaching by exited founders who've been there.

If this resonated and you want to dive deeper, shoot me a DM.

Step 1, A Look Back: In my last post, I talked about creating the liminal space - the gap between who we were and who we are becoming. But, to clarify where you’re going, first you must look at where you’ve been...

It’s easy to focus solely on what to build next. It feels productive. It keeps the high-performer persona safe. But if you rush to the finish line without seeing the patterns that drove you all year, you just end up running the same tired race with a new trophy.

The most potent clarity for your future is hidden in the truth of your past. You have to close the chapter that was 2025, not just slam the book shut.

Give yourself 30 minutes to answer the following questions:

1. What happened this year?

Go quarter by quarter. List the major milestones, professional setbacks, and relational events. Don't curate the list - just the facts.

2. What are you most proud of this past year? Personally? Professionally? In your relationships?

Look past the revenue. Where did you lead from authenticity, bravery, or kindness? Where did you choose the hard, quiet thing over the loud, easy one? 

3. What were you most challenged by this past year? Personally? Professionally? In your relationships?

This is where you drop the armor. Don't self-protect - name it directly. These pressure points show you precisely where your growth is waiting.

4. When did you feel most alive?

These are your signals. For me, it’s rarely when I’m winning. It's often when I’m up against an edge, totally exposed.

5. What would you do differently if you could?

This is less about regret and more about optimizing for wisdom. Name the specific choices you’d reverse. You can't change the past, but you can harvest the insight.

6. How are you different based on what you experienced this past year?

Look for the subtle shifts. Maybe you shed a layer of armor. Maybe you found the strength to say no. Identify the permanent psychological or relational change that was forged in the fire of this year.

7. What behaviors, habits, or people held you back this year? Which helped you evolve?

Be ruthlessly honest. Bring awareness to the negative whilst celebrating the positive.

8. What lessons did you learn this year? What did you learn about yourself? What did you learn about yourself as a leader?

Every event is just data until you extract the salient principle. What are the 1-3 core, non-negotiable truths about leadership, life, and your own patterns that you now know for sure?

9. Tell the story of your year.

Complete this sentence: “When I look back 10 years from now, this year was the year that...” This distills the whole chaotic experience into a single, mythic arc.

The lessons from this exercise are some of the most valuable assets you own.

Tomorrow, we move into Part Two: The Eulogy 

And, if you'd like access to the full Annual Reflection Template, comment "Gimme gimme" below.

Step 6, Setting Goals for Momentum: You’ve brought a clear definition for success in 2026 into focus, and with that, you’ve done the hardest part. Now it’s time to develop the plan to make it a reality...

When building an action plan, the key is to focus on building momentum. Feeling like you’re succeeding can be the difference between going that extra mile or letting “just this one” slip.

Traditional goal-setting processes can actually be demotivating to people trying to make a change because of the uncertainty inherent in the change process.

Instead, build momentum by separating the actions you take from the outcomes they produce and anchoring the success of your efforts to things that are in your control.

Intentionally doing so is the key to creating momentum without burning out.

By allowing yourself to define “success” as having completed the actions, and ignoring the outcomes (apart from regularly scheduled analysis in which you can dial in your actions ⇒ outcomes pipeline), you position success entirely within your control. 

Let's do it:

1. From the three definitions of success you set out, choose one outcome you want to produce (best to do one at a time, though you can return here as many times as you need for additional outcomes).

2. Chunk that 12-month outcome into outcome-based milestones at six, three, and one months.

“What would I need to have accomplished by six months to be on pace for my 12-month goal?” “What would I need at three months to be on pace for my six-month goal?" and so on.

Once you have locked in desired outcomes at one, three, six, and 12 months, shift your focus to actions.

3. Reviewing your most near-term outcome, answer the following question: What actions will I need to take to produce that outcome?

Note: actions must be completely within your control!

4. Check in with yourself: Are you ready to commit to taking those actions?

• If no, own proudly the reality that you’re not yet ready to create those results.
• If yes, put them into your diary, task management software, or however you manage to-dos, and commit to doing those tasks. The important part is to commit to doing the tasks, independent of the results they produce.

This framework is intended to be revisited and iterated upon periodically throughout the year. Many choose a monthly or quarterly cadence.

• At the regular cadence you choose, use actual data to validate your assumptions around actions ⇒ outcomes.
• To do this, once per month/quarter, dispassionately analyze whether the actions you’ve taken have produced the result you expected. 

If so: Continue on with your action plan. 
If not: Revisit this exercise, adjusting the time frames accordingly. 

What is the one non-negotiable action you are taking tomorrow that is completely within your control?

Stay tuned tomorrow for the final exercise of the reflection template.

And, if you'd like access to the full Annual Reflection Template, comment "Gimme gimme" below.

Step 4, Gap Analysis: You have spent the last three days defining two things: The reality of where you are (The Look Back). The highest vision of who you could be (The Eulogy & Five Lives). Now things get harder...

Before moving on to the questions below, review the reflections you made while completing the first three exercises. Then, please answer the following questions as honestly and courageously as you can. Do not limit yourself to what's "reasonable."

1. Thinking back to your Eulogy and Look Back, list the key changes you’d have to make in order to justify such a beautiful eulogy. 

2. After reviewing your Five Lives exercise and your Look Back, list the key changes you’d have to make to ensure you didn’t leave important parts of your life unlived. 

3. Review each of these lists and identify those changes from each that scare you.

4. Ask yourself: “Am I ready to make these changes?”

The relevant commitment is not to the outcome but to the process. Analogously, the question is not whether you want to lose weight but whether you are willing to stick to the diet that gets you to your goal. This is an anthropological exercise, not a creative one. The goal is to really look internally to see if you're ready to do what's necessary. If not, that's perfectly ok.

If you are ready to make the necessary changes from the questions above, write down your commitment to memorialize it for yourself. Share it in the comments if you think that'd help keep you accountable.

If you feel you aren’t ready to commit to the changes you listed above, perhaps reviewing this article will help: https://lnkd.in/gmARwFRQ

Tomorrow, we will cover what success really looks like and how to define it for 2026.

Keep going!

And, if you'd like access to the full Annual Reflection Template, comment "Gimme gimme" below.

Step 7, The Postcard: The primary risk to any intentional change is inertia. Specifically, that your best intentions get lost within the never-ending sea of life/work/family tasks, and before you know it, another year has passed... 

Don’t let that happen.

Create accountability for yourself, to yourself, by writing a letter to your future self, which you’ll schedule to have automatically delivered at a future date.

This way, whatever happens in the year ahead, you know that at some point in the future you will be reminded of your commitments, and have occasion to reflect on how well you kept to them (remembering that the key is keeping to actions taken, not outcomes produced).

In this letter, share your reflections from these exercises, your learnings, and any commitments you are making to yourself.

Schedule the email to send to yourself on June 30, 2026, using your mail client’s “Schedule Message” feature. 

And with that, brings the close to my annual reflection template.

------------

This is it.
This year.
This minute. 
This moment.

Even if it seems like this couldn’t possibly be it. 

That feeling is it, too.

Thank you for everything you brought to the world in 2025, for everything you are, and for everything you are becoming. 

Thank you for taking the time to reflect on your one weird, precious life, and by doing so giving yourself the opportunity to create it more consciously. 

Thank you for being unabashedly you, and not anyone else.

There will be a lot of moments in 2026. Co-create them with the ones you love.

I wish you the best of luck in diving deep, leading authentically, and bringing your unique story to the world this coming year.

And, if you'd like access to the full Annual Reflection Template, comment "Gimme gimme" below.

---

Proud to coach with Inside-Out Leadership, CEO coaching by exited founders who've been there.

If this resonated and you want to dive deeper, shoot me a DM.

Step 5, Defining Success: “What does success look like to you?” “How will you know when you have it?“ Those are two of the most powerful questions for leaders...

When the answers are fuzzy, leaders can feel stuck and uncertain. 

Clear answers, however, create a powerful creative tension between leaders and the results they want to achieve. A clear vision for success illuminates the path and propels leaders in the direction of their dreams.

So what does success really look like to you?

Answer the following questions in order:

1. What would success look like for me in 2026? 

Start this section by journaling free form, allowing ideas to flow. Then, to end this section, see if you can summarize your journaling into 1-3 concrete definitions of success.

Now we’re going to explore those definitions more deeply, to enable all parts of yourself to understand and align around what you really want. 

2. What will having that success do for you?

Answer as many times as you need to drill deeper into what’s behind your desired outcomes.

3. How will you know when you have it? 

4. What (or whom) might you lose, that you value, when you have this outcome?

5. Considering all your answers above, capture the 1-3 specific, measurable outcomes that would constitute success for you in 2026. Each measurable outcome should be no longer than a sentence.

You may think this exercise is about setting aggressive targets... It's not. 

It’s about establishing intentionality over chaos.

When you define success this precisely - drilling past the surface goals to name the cost and the why - you achieve two profound shifts:

• You Build Self-Trust. You stop outsourcing your worth to external expectations and start leading from internal clarity.
• You Create Productive Tension. The clarity itself creates the necessary pressure - the creative tension - to act. When you measure it, you can't hide from it, and the awareness alone begins to cause change.

This work is how you begin generating momentum from a sustainable, powerful source: clarity and truth.

What is the single most powerful, measurable outcome that defines your purpose for 2026? 

Share below - I'd love to hear it.

Follow along for the next reflection exercise. 

And, if you'd like access to the full Annual Reflection Template, comment "Gimme gimme" below.

Michael Phelps won 28 Olympic medals across four Games. Yet, after London 2012, despite winning six medals, he was in deep crisis and contemplated ending his life...

He's not alone. Will Smith has talked about "Cliff Top" being just as lonely and hard as "Rock Bottom." Jim Carrey has said similar. The list goes on.

So what's going on?

This is a central paradox of high performers in any field. The fierce drive that propels you to the top of your game/market is the same corrosive force that leaves you hollowed out at the summit. For founders, we chase the exit unquestioningly, so focused on attaining the goal that we never stop to consider what might come after.

What nobody tells you about an exit is that the leaving is its own special kind of challenge. Special, and yet surprisingly consistent from person to person.

Here's the typical process:
1. Exit.
2. Existential vacuum.
3. ???
4. Realigned to purpose.

Some founders, confronted with this vacuum of purpose, jump immediately into the next thing. If you exit your consumer app and can find purpose in an even bigger consumer app, bless your heart, please run with everything you've got. Come read this post back after your next exit. 

If you find yourself struggling, however, know that you're not alone. Many founders struggle with step 3. I did. I experimented, jumping into each project with the same gusto, but I kept finding that I couldn’t recapture that sense of unquestioning purpose. Try as I might, it just felt different.

The salient issue, I've learned after coaching dozens of founders through their post-exit transition, is that as we mature, the way we construct meaning changes. 

At first, we FIND purpose. But eventually, we must CREATE it.

Finding Purpose:

• Purpose is found in the world and brought into yourself.
• Meaning is derived from what, and how much, you get.
• Success is a function of the outcome achieved.

Creating Purpose:

• Purpose is found inside yourself and brought to the world. 
• Meaning is built from what, and how much, you give.
• Success is a function of the work done and the motivations behind it.

Phelps found his breakthrough by checking into intensive treatment in 2014.

He returned in 2016 to win five more golds in Rio, but he swam from a radically different internal foundation. He swam from love for the sport, not the desperate need for meaning. The achievement was the same, but his entire relationship to it had transformed.

Today, he has moved beyond the pool to create purpose as a vocal advocate for mental health. By sharing his struggle, he is building a meaningful life that a gold medal alone never could.

Only you can tell if it's time to start your own work. If so, here's a question for you to get started on your path to rediscovery:
 
How can your career be most useful to others?

Step 3, Five Lives: This exercise, modified from Julia Cameron’s The Artist’s Way, is a powerful weapon for injecting nuance back into a one-dimensional life... 

If you had five other lives to lead, what would you do in each of them?

I would be an NBA player, a physicist, an astronaut, a fiction author, and a monk. 

You might be an entrepreneur, a scuba diver, a cop, a writer of children’s books, a football player, a belly dancer, a painter, a performance artist, a history teacher, a healer, a coach, a scientist, a doctor, a Peace Corps worker, a psychologist, a fisherman, a minister, an auto mechanic, a carpenter, a sculptor, a lawyer, a painter, a computer hacker, a soap-opera star, a country singer, or a rock-and-roll drummer.

You only get one shot to experience life. Don’t leave important parts unlived.

Instructions: 

1. List the things you’d do if you had five additional lives. Whatever occurs to you, jot it down.

Do not overthink this exercise. The point of these lives is to have fun - more fun than you might be having in this one.

2. Look over your list and select one life. Then figure out the smallest way you could begin to live it, this week

For instance, if you put down “country singer,” can you pick up a guitar? If you dream of being a cowhand, what about some horseback riding?

"One amazing aspect of another life I want to incorporate into this one is..."

3. Final Step:

Commit to taking the first step listed in step two in January 2026.

"I’m going to take this small step beginning in January 2026..."

Feeling fired up and want to make an impactful change quickly? Consider adding one or both of these bonus credit steps:

• Bonus credit 1: Don’t wait until January. Get started this week. 
"I’m going to take this small step towards beginning it this week..."

• Bonus Credit 2: Pick two lives.
"A second amazing aspect I want to incorporate is..."

Your commitment to your internal life may be the only true competitive advantage you have left. 

The question is, are you ready to allow your life to be as rich and complex as your ambition?

Which part of your true self are you suppressing for the sake of "output"? 
Share your unlived life below.

Follow along for the remainder of the annual reflection sequence.

And, if you'd like access to the full Annual Reflection Template, comment "Gimme gimme" below.

In 2017, Uber lost its CEO, its reputation, and nearly its future - because the culture became toxic and turned against itself. I’ve been there, too, without the global brand, but with all the danger...

Uber's early success was fueled by aggression, speed, and internal competitiveness. These traits fueled their rise, but without emotional regulation or boundaries, they became catastrophic liabilities.

I've been in that pressure cooker.

Years ago, I scaled my company from 15 employees to 75 employees in nine months. Our corporate culture was completely unprepared for the stresses of such rapid scale-up.

I talk to founders every day who face the same dilemma. They do what successful people do: they try to fix it. They spend a fortune on consultants, off-sites, and "culture work."

Uber is the masterclass in this.

They hired a former U.S. Attorney General to write a 12-page report with recommendations, fired 20 people in one shot to signal 'change', and ditched their original values for a new list of corporate-approved principles.

But you can't fire or spend your way into a new culture. By pushing new cultural frames without acknowledging the current ones, you breed resentment and cynicism from those who see the culture for what it actually is.

To truly change your culture, first, you must stop trying to build the culture you want and start by looking at the culture you actually have. Only then, working from a foundation of what is, can you begin to make change.

Here's how:

1. Look Inside Your Company

Anonymous surveys are a great tool to understand how your employees view your culture. Anonymity is key.

A survey like this communicates to your employees that you understand the importance of culture and that you will presumably listen to what they say. However, if you take this route and do nothing to address the feedback, it can break trust. 

2. Look Inside Yourself

At some point in every entrepreneur’s journey, they realize that their company is a manifestation of themselves. This offers a shortcut: you can understand your corporate culture by understanding yourself.

Are you late to meetings? That’s your culture. Others are late, too. 
Do you hold yourself to the grindstone, sacrificing holidays to make more progress? That’s your culture. Others do that, too. 

While most entrepreneurs resist this, looking internally is the most reliable route to determine your culture. For those brave few, it’s best done with either a 360-degree survey, or a dedicated coach to help you see your blind spots.

Great. I’ve reconciled with my current culture, and I still don't like it. Now what?

Once you've identified how you're creating the culture you say you don't want, changing it is simple:

Step 1: Change yourself to live by the values you want the company to live by.
Step 2: Write the values you live by on the wall.

And if you’re wondering, yes, that’s what we actually did to transform our culture at speed.

Simple, yes.

But not easy.

I used to be a virtuoso of the "Founder's Glance." In 30 minutes, I could diagnose a hemorrhaging sales pipeline or a toxic board member with surgical precision. It took me 15 years to sharpen these instincts into a blade...

And then GPT-4 learned it all in an afternoon. 

For the modern founder, watching AI automate your "unique" expertise is far more than merely a professional crisis. It’s an existential punch to the gut. 

The standard advice is to pivot - to move from "knowledge" to "wisdom." We’re told that our value now lies in judgment, in knowing which fires to douse and which to let burn. There is some truth there, certainly. 

But here is the deeper rot that no one wants to name. 

Tying your worth to "wisdom" is just as brittle as tying it to knowledge. Because wisdom is still something you possess. It is an accumulation, a trophy case of experiences. And anything you possess can - eventually, inevitably - be taken from you. 

I grokked this the hard way in 2020. 

The day I signed the papers and officially ceased to be "Ryan the CEO," the armor evaporated. Without the title, the expertise, and the authority, I realized with a terrifying clarity that I had no idea who was left standing in the room. I had spent a decade building a masterpiece of a company, but I was a stranger to the person underneath it. 

The only foundation that cannot be automated is your Integrity. 

Not integrity as a corporate buzzword, but integrity as wholeness - the radical alignment between your deepest values and your daily actions. This requires two things that are infinitely harder than raising a Series A: 

1. Ruthless Self-Inquiry: 

Stripping away the inherited scripts of "unicorn status" and "disruptive growth" to find what you actually give a damn about when the world isn't watching. 

2. The Courage to Lose: 

The terrifying bravery to say "no" to the high-status investor or the lucrative exit because it doesn't match the shape of your soul. 

When I finally put down the Successful CEO costume, the world didn't end. 

It began. 

And I became a more integrated human being. 

Inside-Out Leadership was born from that wreck. We help founders find the floor that doesn't drop out when the technology changes. 

If you’re tired of being at war with an algorithm for your sense of worth, let’s talk. 

Shoot me a DM. There's another way.

Inside each of us is the work we’re meant to do - the gift life placed in us long before we knew how to name it. Most of the year, we’re moving too quickly to notice any of this. This festive season, I implore you to slow down...

Something happens as winter approaches - the world exhales, the pace softens, and a kind of ancient stillness returns. The days grow shorter, the light thins, and the body remembers what the mind has forgotten: that we are not built for endless acceleration. That seasons exist for a reason. That rest and reflection are not indulgences but sacred intervals in the rhythm of a life.

Every December, whether we acknowledge it or not, we are given an invitation.
Not to plan harder or become more productive, but to stop long enough to rediscover the person who has been doing all the planning and producing in the first place.

For years, I refused that invitation.

I moved at a speed that made introspection impossible. The constant pressure of building - raising money, hiring, meeting expectations, staying ahead - created a kind of internal weather system that drowned out anything subtle. Whenever I even "considered" slowing down, fear appeared instantly. The fear that without motion, I might lose my worth.

These patterns live inside almost every founder I’ve ever coached.
Guilt, fear of falling behind, compulsive motion - not because we want to run, but because stopping forces us to feel the very sensations we’ve spent a lifetime avoiding.

So during the holidays, I do the opposite of what my instincts command:
I deliberately downshift. I empty my calendar. I create long stretches where nothing is happening, and no outcome is being pursued.

I'll be honest, when you do finally slow down, it’s fucking uncomfortable.
Your mind tells you to get up. Your body wants out. Everything in you tries to pull you back into doing.

But if you stay with it, even for a few minutes longer than you want to, something shifts. The guilt softens. The fear loses its grip. And beneath all that noise, a quieter signal starts to emerge.

A spaciousness. A kind of inner clearing. A subtle pull toward a direction that doesn’t come from ambition or fear, but from somewhere deeper, older, truer.

Over the years, I’ve learned to trust that pull. It's often quiet, but it reveals the next piece of work life is trying to cause through me - the work I could never have strategized or forced into existence.

This is why December matters.

It’s the opening between years.

A liminal space that allows us to see our patterns, question our momentum, and listen for the whispers drowned out by eleven months of noise.

In my next seven posts, I’ll share a reflection sequence designed to help you step into that space with intention - one exercise per day, each one deepening the clarity that emerges when you stop trying to control everything and start listening for what wants to come through.

Stay tuned!

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