How to completely change your life in 365 days

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How to completely change your life in 365 days

A thought experiment, two questions and a story that changed my entire life

Scott Barker

May 05, 2026

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Welcome to edition #16 of The Wake Up Call, this week I write about:

A thought experiment & two simple questions that changed my life
A personal story & announcement that has been six years in the making

This newsletter is for anyone who is questioning the endless pursuit of more. Stories exploring the psychology of meaning, acceleration and modern ambition. Each week I write one non-fiction essay for the mind or one fiction story for the soul.

This essay is a personal one. I will continue my series of writing on The Acceleration Decade after this edition.

You haven’t heard from me in a while. I took a little break from publishing. I could feel myself starting to write for an audience, rather than writing to understand myself/the world better so I hit pause.

A little pause to take my own (and Brad’s) advice to slow down, touch grass and challenge myself to create, contribute & love from an authentic place again.

There has also been a lot of exciting changes in my life that have taken up more of my time. I wrapped up my five months in India with a ten day silent retreat, meditating for ten hours a day.

It’s been a whole year now that I’ve been on the road with my backpack looking for ways to live a happier, healthier, more meaningful life.

During this last stint, I got really clear on everything. Perhaps the most clear I have ever felt in my life.

I now know how I want to spend this next phase of my life. I’m excited to share how I got there. It took a long time but I finally have an answer to the question:

What’s next?

Let’s get into it.

for.and.from.the.mind

It’s been just over a year since I left everything I know behind.

And every morning for at least the last nine months I have written the same two questions in my journal:

_Who shall I be today?
What shall I do today?_

Two ridiculously simple questions. The simplicity masks how powerful these questions really are. Within that pair of five words lies almost all of our human agency.

They are perhaps the most personal questions that you can ask yourself.

Who do I want to be in this life? How do I want to spend my short amount of time on earth?

But framed as they are above, these questions strip away any fantasies of the future. It’s not about building yourself into the perfect version of yourself. It’s not about building the perfect life in the future.

It’s about today. It’s about right now. The only moment that ever really exists.

“How we spend our days is, of course, how we spend our lives” - Annie Dillard

There are many things we cannot control in life. Right now we feel that more than ever but these two things are very much in our control (even when they feel like they are not). This is what every human has autonomy over.

Every day, you wake up and you get to decide who you want to be on that given day. Yes, you must battle against all your neurosis, the experiences that shaped your view of the world, your negative habits but on any day you can choose to be something different. That is within the realm of possibility for each of us.

And every day, you wake up and you also get to decide what you want to do on that given day. Now, as adults, we have responsibilities to our loved ones, we have jobs that pay us to be there and a myriad of other things we feel as if we must do. But the reality is, you don’t have to do any of those things. You get to decide where each minute goes.

In my former life as a venture capitalist and tech executive, I could not see the freedom I held in my being and doing. It felt as if my personality/sense of self was already set and I had to make due with who I was. And it felt like I had built a life so big that my responsibilities and task list were set weeks in advance. I just had to find a way to somehow get through each day. I was a prisoner in my own life. Eventually that way of living made me sick.

But we are not bystanders in our own lives. Just because we’ve set ourselves on a path, does not mean we need to see it through to the very end.

I went as far as I could in the world of performance and success…and it broke in a way that required a lot of space and deep tools to fix.

I do not believe everyone has to take the dramatic and drastic steps I took to change my life but it was necessary for me.

Only once I stepped down from the fund, sold everything and slowed my life way down could I create space to focus on answering those questions from a place of wholeness. I’ve circled around those two questions again and again. I’ve likely clocked over one hundred hours of meditation/contemplation on them.

One of the things I noticed is how much longer it took for me to see/feel clearly again. We’re always in a rush to reinvent ourselves but the truth is, if you shift too quickly then you’ll just be taking all your old frameworks with you into your new world.

I’ll share my answer below in hopes that they make you think of your own.

Who shall I be?

I would like to be someone who is deeply connected to themselves and the natural world around them. Someone who has enough peace and equanimity in his daily life to seek truth and express that truth. A man who has the courage to take action to help create a better future for all. And one who chooses love over fear as often as they can.

*I tweak my answer slightly each day to suit the particular set of events/tasks I have ahead. Some days I need more peace, others more courage. We are much more malleable than we think.

What shall I do?

I would like to spend my life transforming fear/pain into love/passion through creation and action. And helping others close the gap between their external world and internal reality.

*I’m aware that sounds corny but I have tried many, many times to re-word it in a way that doesn’t make everyone roll their eyes but I can’t…so we’re stuck with it. I think I’m ok with being corny these days.

How do I keep myself accountable for being the human I want to be and doing the things I was called to do when life starts moving fast?

I keep it dead simple. I run a simple thought experiment at the end of each day.

How to measure your life:

Look at your previous day and ask yourself:

If I had to live that day over and over again for the rest of my life, would I be happy?

If the answer is yes then you’re on the right track. If the answer is no, make some adjustments.

Every day you choose who you want to be. In part, you become that person through the actions you take which leads me to the doing part.

This clarity around what I want to do was crystallized for me last October during my time at a 5-MeO-DMT Retreat and since then I have been looking for ways I can serve that mission.

The whole idea behind this newsletter and my podcast is to help people wake-up before their wake-up call ie. realize what’s important in life before it’s too late. I will continue writing and sharing my thoughts but somehow that did not feel like enough.

I want to get my hands dirty and build again. That sent me down many rabbit holes, mapping out the different businesses I could create next in service of that mission. Part of that was taking stock of all the things that had helped me on my own personal journey.

What helped me transform my own fear or pain into love and passion?

Many things came to mind: long treks in nature, the silence in monasteries, the stillness at ashrams, the learnings from yoga retreats, the wisdom found in ancient scriptures, time spent in community.

It all worked but it also felt disjointed and I couldn’t figure out how to connect it all.

But there was one place that kept coming up in my mind that encapsulated it all. A place that felt like home.

the.big.announcement

This place is a beautiful sanctuary called Enfold on a little island in BC, Canada run by two incredible humans and dear, dear friends.

This place had felt like home for a long time and I knew that it felt like home for thousands of others too.

At first I thought, what if I could build something like Enfold?

They were a living, breathing example of helping transform fear/pain into love/passion.

…but hold on, let’s rewind the tape for a second. It’s a bit of a crazy story.

I first ended up at Enfold quite serendipitously about six years ago. A good friend of mine actually gifted me the experience of going to one of their retreats.

It is a five day process that uses psychedelics, coaching, and various therapies to help you awaken to your life again. To access parts of you that you thought you lost long ago and unlock the dormant answers within.

Their core offering involves 5-MeO-DMT (the strongest psychedelic known to mankind) but the medicine itself is really only part of the process. It is a tool within a structured environment and part of a broader system of transformation.

To say this had a profound impact on my life would be an understatement. I had been on the path for a few years by then but I had yet to witness a container like this before. It was a magical place that felt like it was from another planet, yet the people leading it were very much grounded in this reality. They did not take themselves too seriously, they laughed often, loved to come up with crazy business ideas (like me), they were never preachy and had incredibly full, successful lives before being called to this work.

It was deeply spiritual work, but grounded. Real. Not performative.

The two founders, Steve Rio and Austin Austin, would end up becoming very important in my life.

That first experience gave me a glimpse behind the veil. A glimpse into what source, unconditional love and faith feels like. And for a while, everything made sense.

Unfortunately like all humans, I am very forgetful. Even when I learn the most important lessons of my life, I have this way of forgetting them as time passes. I actually have a tattoo around my knee that says: Life is just a series of remembering.

I went back to my incredibly demanding life but something had shifted inside of me. I could see the masks/characters that I put on in different parts of my life. When it was time to be VC guy, time to be sales guy, time to be dinner host, time to be fun/party guy. None of them felt like the real me.

But, like any good high-performer, I have my black belt in compartmentalization so I pushed those thoughts below the surface and doubled down on outward success. If I achieved enough then I could buy back my time and rediscover the real me again in the future…that was the plan.

Those next five years were far and away the most ‘ successful’ years of my life. I co-founded and built a VC fund from scratch, grew a community of the best tech execs on the planets, invested in hundreds of incredible founders, bought/built a media company and raised one hundred million dollars.

For much of it, I was miserable, anxious and depressed.

The reality is all of that ‘success’ had a cost. The cost was being completely disconnected from my mind, body and soul. My engagement fell apart, all of my friendships were strained since I was never around, I rarely saw my family, I had to give up my best pal (my cat) due to too much work travel, I ended up in the ER with an stress-induced ulcer, I was taking pills to focus, more pills to sleep and drinking daily just to try find some peace.

In the middle of that period, I hit what I thought was rock bottom at the time. After staying late at the office (again), I came home to find my fiance at the time waiting in the living room, she wanted to ‘take a break’ , this completely blindsided me and with my stress-levels already through the roof, I did not take it well. I called some friends and for the next forty-eight hours proceeded to numb myself every possible way I knew how. Drugs. Alcohol. Gambling. You name it. It was not pretty.

Eventually my body started giving up, I was having the darkest thoughts that one can have and I broke down. I did not know where to go. I did not know who to turn to. For some reason, the only place I wanted to go was Enfold. I was in the eye of the storm and needed some sort of anchor.

I called Steve knowing that it was a long shot. They were running retreats all the time that were booked up months and months in advance. I told him what was going on and he didn’t even hesitate when he said: “ Get on the next ferry. I will pick you up. Stay as long as you need.”

As you’ve likely experienced, the world does not stop when you go through tough periods like. When it feels like your whole world is crashing down, the world just keeps moving. I needed a place where the world would stop for a second. They gave me that place.

I do not know how they did it. I’m sure they had to push guests into other dates or at the very least completely readjust all of their own plans that week. There was no medicine used that week but they created an environment for me to do the deepest unearthing, processing and healing that I’ve ever done in my life. I’ll never be able to repay the kindness and presence they showed me that week.

But it also dawned on me that this is just what they do, this was just a normal week for them, this is how they have chosen to spend their lives: helping others transmute their fear/pain into love.

After that week, I knew that one day I would like to find a way to do the same for others.

That felt like a far away fantasy though. It did not feel possible within the framework I was operating under so I went back to my old, very intense life but this time I stayed in that period of remembrance for much longer and my life slowly became more enjoyable again.

Fast forward another few years (because this story is getting too long)and I fall back into deeply rooted patterns of trying to over-achieve, self-sabotage, prove myself to anyone/everyone and chase the next big thing. Eventually I ran my body/mind into the ground again. It got bad. Really bad. Bad enough that I could no longer do it anymore. I could no longer play the character I was playing. This would be the last time.

That’s when I stepped down from the venture fund I co-founded, I sold my house (and everything in it), put what was left in a backpack and went to travel the world to try to figure out some better questions to ask.

I found them in the two, almost comically, simple questions above.

This fall, I travelled all the way back from Lombok, Indonesia to Enfold to participate in another ceremony (we actually filmed it and a documentary will be coming out at the end of the year). It was a much more challenging experience this time around but I came out with my answer to the second question.

Then over the course of the next few months, I figured out how I was going to bring my answer to life.

My thoughts switched from, what if I could build something like Enfold? to what if I put my ego aside and used everything that I’ve learned to support Enfold in their mission?

Now, looking back, the path here feels almost inevitable.

As of today, I am honoured and humbled to finally announce that I’ll be joiningThe Enfold Institute as a Partner and Managing Director.

This is not me completely leaving the world I came from behind, more like trying to help fix parts of what I saw was broken inside of it. It’s clear that a lot of the systems and stories we’ve relied on up until now are breaking down.

It’s an important period of time for: 1. modern health 2. the psychedelic space 3. humanity as a whole

Our modern health system is going through massive upheaval as people start to take their healing into their own hands.

Humanity is about to enter what I call The Acceleration Decade brought on by rapid advancements in technology.

And the psychedelic space is heading into, what Paul Austin calls, the Third Wave. This is a movement in psychedelics that is not anti-science like the 70s. And it’s not narrowly biomedical like the second wave in the 2010s.

It’s the middle path: science and ancient wisdom. Evidence-based tools alongside contemplative traditions. Rigor without reductionism. Reverence without dogma. An approach that can hold the complexity of the human experience without needing to compartmentalize it. An approach that recognizes that “one-size-fits-all” simply won’t work. This is the wave Enfold has been building for. We believe it’s the wave the world is ready for.

- Steve Rio, Co-Founder at Enfold

You can read more about the mission behind Enfold, the Third Wave and our vision for the future, in this article (well worth the read).

It feels like it’s all converging and I want to be on the front lines.

The world faces many problems right now. And no, psychedelics are not the answer to all of them but they are a part of the solution.

Modern mental, physical and spiritual health is evolving rapidly. And it needs to. I believe our future depends on it.

Our inner collective consciousness must evolve in order to meet the growing challenges of our outer world.

We need happy, grounded and connected human beings in order to co-create a better future for all.

This is not another project for, this is not another job, this is not just another company, this work feels like what I was put on this earth to do.

latest.podcast.episode

In the following interview I sit down with Ian Koniak, a highly successful Founder/CEO, Coach and former #1 Enterprise Account Executive at Salesforce. Ian opens up about addiction, identity, integrity and the tension between who you are and who you are meant to be.

Ian shares what it took to break the cycle, rebuild trust and step into a life rooted in honesty and service.

You can listen to the full episode here.

Please support our partners (they are all doing incredible work in the world)

Dreamfuel - the leading mental performance coaching platform for technology teams. As a Wake Up Cal l subscriber, you are eligible for a free 1-1 or team coaching session.

Enfold - five days can change the course of your life forever. If you mention Wake Up Call , your application will be prioritized.

Second Harvest - a community for accomplished people ready to find clarity & connection in their next chapter. Check out their upcoming Summit in Lincoln, MA.

That’s it, thank you all for being on this journey with me. It’s been a wild one.

As of today, I guess this is my new career path :

College dropout
Bartender
Entrepreneur
Account Executive
Sales Manager
Business Development Rep, Tech
Business Development Team Lead, Tech
Business Development Manager, Tech
Head of Partnerships, Tech
Director, Strategic Engagement, Tech
Co-Founder + Partner, Venture Capital
Homeless backpacker, Advisor + Podcast Host
Managing Director + Partner, Psychedelic Institute

Career paths aren’t real, you’re never stuck, carve your own way, follow your heart. All the cliches are true.

All love,

Scott Barker

*To try to keep the integrity of this project, I don’t use AI for any copy-writing or proof-reading (only research and debate). I am a human, I write like a human and humans make grammar/spelling mistakes. Writing mistakes might not be around for much longer so I hope you enjoy them while you can :)

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