A lazy person’s guide to planning an epic 2024.

“I don’t know what’s wrong with me,” I told her, crying my eyes out on the phone.

I hadn’t slept in a few days.

I didn’t want to eat.

Life had reached a sorta standstill.

I was spending money like it was going out of style and the anxiety and fear that built up in my body was starting to pour out in the moments before I went to sleep.

Making movies is and was expensive, but did it have to be this pricy?!

I thought to myself.

And so, after a few nights of this, I was starting to reconsider whether or not I wanted to actually be alive.

And it was in that moment that I decided to leave my furnished apartment in Los Angeles, and move back home with my parents.

Fortunately, they were living nearby — as Snowbirds do — in Phoenix, so the trek wasn’t all that bad.

But I still remember that period of my life being particularly brutal.

That was right around the time that I stopped planning things — simply because planning felt brutal.

I had planned everything to this point, over the past few years — in journals, notebooks, extensive Evernote pages and, eventually, Notion (another planning software).

Meticulously, I planned.

In Notion, I had done a daily reflection practically every day since the middle of 2020.

Suddenly, I stopped.

It had become too painful.

Each day, in those Notion reflections, I would honestly reflect on my happiness levels — and the thought of just putting a “1/5” day-in and day-out felt too, too brutal.

(But maybe those are the moments in which we should be the most honest with ourselves.)

So I stopped planning.

I hit the pause button — after all, we were navigating a breakup with a business partner that wasn’t going particularly well; the production that we’d been building up to over the last few months had stalled; and since it was self-funded, I would ultimately be on the hook to pay everyone out for the delays.

It sucked — no, no, it was easily the worst I’d ever felt in my entire life.

I had learned to associate money with value — and when I felt like I wasn’t spending it wisely, then my value as a human-being dropped through the floor.

So, I stopped filming.

I stopped writing.

And I stopped planning.

The actions and behaviors that had gotten me to this point in life — take small risks, then eventually take big ones — had clearly not worked.

So I fell apart.

And with the rest of my money, I invested it almost entirely into therapy and other self-help related stuff.

(And then a relationship that ultimately fell apart, too. Which was fun and cathartic and all that jazz.)

This is the story about how I, after a year-plus of not really planning — re-started a process that has yielded plenty of success over the years.

Financially; spiritually; and emotionally.

Let’s. Dive. In.

For many years, I wasn’t honest with myself about how I viewed money.

I would tell people, “Oh, it’s no big deal — it’s just money.”

But I would panic internally.

Money, to me, meant: security; it meant love; and most importantly, it meant value.

If I was making good money, I had good value.

If I wasn’t, I was essentially valueless.

This can be debilitating because, naturally, money comes and goes in waves.

And this is true of even the wealthiest people in the world — their wealth fluctuates massively at times.

And when we feel insecure about money — or, more significantly, if we feel insecure about who we are with or without our money — then it can be extremely debilitating when it isn’t going our way.

I discovered this the hard way when, after several years of financial success that yielded me a pretty substantial net worth of over half a million, I’d decided to essentially invest it all into the things I love: making movies.

(And fun — I had a pretty fun life, too.)

My thought was: invest in what you life, and it will come back to you.

I could never even fathom the possibility that that might take years and years and that, in that time, I’d ultimately have to go back to doing client work and working on projects that sometimes paid me less than I earned when I first started to get into video production many years ago.

Life has an incredibly debilitating way of teaching you lessons.

A few months ago, following a breakup, I remember sitting in a tub in an AirBnB I was staying at with my parents while we were visiting my sister and brother-in-law and their brand-new babeh — and I was on the phone with one of my friends who I’d predominantly gotten to know while Nomad-ing around the world, a few years earlier.

I asked him how he went about his life and planned things — he always seemed to be working successfully towards something.

And he told me about this book — now, if you know anything about me, I hate books about entrepreneurship.

(Maybe that’s why I’m so bad at it.)

I love books about anything else — even entrepreneurship-adjacent books like psychology or other self-help things, but pure entrepreneurship?!

No. Thank. You.

(Still, I’ve read most of the big ones.)

And so, he’d recommended I check out the book Traction.

I was in such a low, excruciating place in life — the breakup still felt particularly raw — that I was open to just about anything.

I started reading it — well, listening to it.

A thing that stood out, for me, was this notion of creating a one-page plan for your business and how you plan on approaching it.

I found that compelling — so compelling, in fact, that I decided to apply that same approach to every area of my life.

Here are some images of my different planning sheets + templates:

I typically break them up into…

And that’s essentially the structure of it.

A good friend of mine (and a mentor in a lot of ways) talks about how he refers to this one-page pretty much every week — it is the source of most of his time and energy as an entrepreneur — and initially I was like, “What the fuck?!”

A few months later, I get it.

Having a clear vision and a plan for executing on that is so, so critical in steering your ship in the right direction.

Practically every morning, I step into my morning routine — i.e. Running, biking, cold-plunge, yoga, etc. — and then afterwards, often journal on my day, week, whatever else is coming up.

There’s no one, singular theme — it’s often, “What challenge am I trying to address today, this week?”

This reflection period has helped provide a lot of clarity behind my goals and my vision — the plans that I have in place look remarkably different than they did just two-plus months ago.

(Even aesthetically, I’ve changed them up a lot.)

Spending my time in the morning reflecting on these big ideas and plans gives me the ability to find clarity in the execution of them.

Because often they start off as extremely nebulous and impossible to achieve things — Be The Type of Person Who’s Exceptional at Fundraising for My Projects.

Like, What The Fuck Does That Even Mean?!

So, I think about that.

I start a run with a question — “How do I become exceptional at fundraising for film projects?”

And by the end, a few answers come up…

Ultimately, I chose the latter path — simply because the first one takes time + luck and I wanted to take the pure luck part out of it.

After all, I’m currently living in East Hampton — and it’s a place where people get art.

OK — so that’s a massive leg-up.

Now, how can I use that massive opportunity (and privilege) for good?

For most of my adult life, I’d been acutely terrified of women and dating.

So I didn’t. Date. Women. Anything.

My first girlfriend, I got when I was 24 and we never slept together.

(We tried, but I was scared.)

I avoided it.

Which led to a lot of shame and suffering because, internally, I wanted to connect with women.

Every straight guy does — it’s biological.

But early childhood trauma can often dictate how we interact with and see the world and my trauma had informed me that women = danger.

It wasn’t until I’d turned 26 that I actively started to deal with any of those issues.

It felt like an extremely long time to wait but I feel like we often tackle challenges in our life when we’re ready to tackle them.

So I hired a therapist; I hired a dating coach; I joined a Men’s Group; I asked for help and advice from female friends; I started to open up about my fears quite publicly and with friends and family.

It took years. I’d say it wasn’t until I got to closer to 30 that I ever felt truly safe around women in that was, and wasn’t utterly terrified of them.

And it didn’t start with a goal of — “Find a girlfriend who you connect with.”

It started with this notion of, “Becoming the type of person who would make for a great partner.”

Those changes included:

Many of those changes are still ongoing.

But it never started with a goal.

The goal was simply to inhabit the behaviors of somebody who would be great to be with and grow with.

And it worked — I started to find some success in meeting and connecting with great women.

This is a concept that I stole from James Clear, well before he’d ever written Atomic Habits and the dozens of articles he’s scribed on the topic.

Simply because it’s worked for me — and I’ve often found that specific goals, regardless of whether or not they ultimately come true, just don’t yield the sorta life-changing results that we all hope for.

Things like…

I will endlessly procrastinate on everything — in particular, anything money-related.

I failed to file my taxes in a timely manner because the notion of paying a huge tax bill was utterly terrifying — so I avoided it for months and months and months.

That cost me.

Avoiding problems always costs us — even if, in the moment, we assume that it won’t.

Recently, I’ve started to think about my tasks, and think — “OK, OK — what is the most painful or difficult thing that I need to tackle this week.”

I start with that first — because the longer that brews the harder it gets.

This isn’t always true — there are simply some periods in life or otherwise in which we don’t want to do hard s**t.

Where it feels too excruciatingly painful.

So we put it off.

For days, weeks, months — until it becomes searing.

I’ve started to adopt a mentality, over the past few months of, “If it hurts, it’s worth exploring.”

And now I’ve started to plan my days and weeks around those activities.

So, a project, like…

Might look like…

A lot of these behaviors and routines are often, for me, particularly challenging and hard — and that’s OK.

Things should be hard.

For the longest time, I believed that meticulously planning my shoots was a bad sign and that it would inhibit creativity — creatives have all sorts of half-baked ideas usually designed to avoid turning the act of creating into a laborious activity.

(But the truth is, everything becomes a job eventually. And that’s not necessarily a bad thing.)

And so, I never planned shoots.

Regardless of the budget — if it cost me $7,000 to produce, or $70,000 — sure, I had scripts.

I had a rough idea of what I wanted to see happen.

But I never mapped out the day.

(And when it was mapped out, I’d left that up to other people who were better planners, anyway.)

That shifted a few months ago when, working with a friend to plan out a shoot that she wanted to produce for a course that she was working on, I saw the day-to-day plan, and I thought to myself, “This is brilliant.”

And, at the same time, I thought, “I have never once planned anything this meticulously.”

So I felt bad, too.

(Side-note: Shame can be a pretty good barometer for areas of growth. If it causes deep, intense shame, then it’s probably something that we should work on.)

There’s something strange that happens when you’re accountable to somebody else — you start to hold yourself to a higher standard and, often, do the thing you say you’ll do.

A study by The American Society of Training and Development (ASTD) found that if you tell someone you’re committed to completing a goal, your success rates jumps to 65%.

Pretty good.

But even better — if you have a specific accountability appointment with that person (say once a week), your success rate jumps to 95%.

Accountability is easily the most powerful means of actually committing to and doing something that you want to do.

And this can take the form of a bunch of different things —

All of these are great ways of seeing what works (and sticks).

I was talking with a friend back home about growth and change and he was discussing how he’d lost a massive chunk of weight over the past few years — 100+ pounds, if I recall correctly.

And he was saying that, yes, life and fitness and all that jazz had become easier, but he didn’t really feel differently.

More confident, sure, but only marginally so.

And I think about that a lot when it comes to change in life — can we continue on the same course that we’re going and be perfectly content with life?

Yes, absolutely.

But the same problems will continue to come up time and again — people might enter and exit our lives seemingly at random; the financial or personal challenges that we run into time and again will continue to rear their nasty heads; and the changes that we want to make in terms of personal growth or lifestyle or otherwise won’t ever come to fruition.

And if you ask my parents, they’re fine with that.

They’ve carved out lives that they seem to enjoy, and don’t really want to change.

But for many of us, that reality is much harder to swallow.

Growing is painful, though.

I’ve had to learn to take a lot more responsibility for my spending and my unwillingness to truly invest my time and energy in making my personal projects work.

In fundraising; in asking for help and support; in putting myself out there.

It has caused an overwhelming amount of suffering over these last few years, for me and several of my collaborators.

And so, I need to grow.

I don’t know exactly what that will look like, but I do know that it will be difficult.

And that there will be plenty of moments where I’ll go, “Fuck this,” and throw in the towel.

And that’s OK — I think the first thing we need to accept is that growth is painful.

Similar to a new muscle-group, anything that involves stretching ourselves and pushing ourselves beyond our zone of discomfort will involve intense struggle.

Because there’s always this voice that has convinced us, “You can’t do that.”

And that’s really what we’re fighting — not our ability, really, because ability can always be cultivated, but that voice.