Life Operations · The JOAT Journal
How to Run Your Life Like a Billionaire (Without Being One)
An inside look at how some of the world’s most successful people actually manage their lives. No, I’m not about to tell you to wake up at 4 AM and buy another planner.
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Over the last decade, I’ve had the privilege of working for founders, CEOs, board members, and some incredibly influential individuals behind companies and platforms that millions of people use every single day.
Some of their names you’d recognize immediately. Others you probably wouldn’t, despite the fact that their influence extends into industries, businesses, and technologies you interact with regularly.
And while I could make this a very entertaining game of Guess Who?, I won’t.
Discretion is a pretty significant part of my job, and I’m not about to start spilling everyone’s business on the internet.
What I can share, however, is the education I’ve received simply by being in these rooms.
Because when you spend enough time working alongside highly successful people, you start noticing things.
Not just how they conduct business, but how they operate outside of it.
How they manage their calendars, make decisions, delegate responsibilities, protect their time, and somehow keep an extraordinary number of moving pieces functioning without personally touching every single one.
And perhaps most importantly, how much thought goes into building the systems that make all of that possible.
I’ve had the opportunity to see those systems firsthand, help implement them, and eventually take what I’ve learned and adapt it for other clients.
That last part is what I want to talk about.
The education you don’t necessarily get in a classroom
One of the more memorable experiences of my career involved working for a founder and CEO who had been invited to participate in executive education at Harvard Business School.
Now, before anyone gets excited, I wasn’t the one attending Harvard.
I was the one helping put some of those ideas into practice afterward.
And I actually think that’s an important distinction.
You can attend an incredible program, read every productivity book on the market, hire the best consultants, and download every organizational app known to mankind.
But none of that really matters if you can’t figure out how to make it work in your actual life.
And that’s where I came in.
They were exploring different approaches to managing their time and responsibilities, and I had the opportunity to help translate those ideas into day-to-day operations.
They got a system that worked for them, and I walked away with knowledge I’ve been applying to other clients ever since. I’d say we both did pretty well.
One of the biggest takeaways involved a combination of intentional time blocking and using project management platforms, particularly Trello, to keep responsibilities organized and moving.
Now, I know what you’re thinking.
A calendar and a project management app? That’s the big secret?
Well, yes and no.
Because the value wasn’t simply having those tools. It was understanding how to structure them, how they worked together, and, perhaps most importantly, how to actually commit to using them.
There’s a pretty significant difference between having an organized-looking calendar and having an organized life.
And I promise, I’ve seen plenty of the former.
I’ve since taken these principles and adapted them for other executives, entrepreneurs, families, and even my own business.
Of course, no two clients operate the same way. Their responsibilities, priorities, personalities, and tolerance for technology can be wildly different.
But that’s part of what I love about this work.
The goal isn’t to make everyone follow the same system. It’s to build a system that actually works for the person using it.
A little side note about the value of connections
I also want to touch on something that I think gets overlooked when people talk about professional growth.
Not every great opportunity is supposed to last forever.
Some of my most valuable connections and greatest learning experiences have come from placements lasting only three to six months.
And believe me, there have been plenty I would have happily stayed in longer.
But I’ve learned to appreciate that sometimes an opportunity serves its purpose within a particular season.
You meet the right person. You learn something you couldn’t have learned anywhere else. You’re exposed to a different way of thinking, operating, or solving problems.
And then you carry that knowledge into whatever comes next.
That’s why I’ll never dismiss project-based work or shorter placements simply because they don’t come with a long-term commitment.
A three-month opportunity can teach you something that changes the next ten years of your career.
I’ve experienced that firsthand.
And it’s a huge part of how Jenica of All Trades became what it is today.
Okay, so how do you actually run your life like a billionaire?
First, let me clarify something.
I’m not suggesting that every billionaire has their life figured out. Money doesn’t automatically make someone organized, disciplined, or particularly good at managing their personal affairs.
Trust me.
But there are certain habits and operational principles I’ve repeatedly encountered among the people I’ve supported that are absolutely worth paying attention to.
And the best part?
A lot of them don’t require you to be wealthy.
They require you to be intentional.
I’ve narrowed down three principles that have been especially valuable throughout my career.
I’m sharing the first one here, and taking the other two quite a bit further in the private members section.
Lesson #1: Schedule your damn rest.
Yes. That’s the first one.
Not wake up earlier.
Not work longer.
Not squeeze one more task into the approximately eleven minutes you’ve somehow convinced yourself are available between meetings.
Rest.
Here’s something I wish more people understood: when you’re constantly operating at full capacity, rest cannot be the thing you get around to once everything else is finished.
Because, respectfully, when is that ever happening?
There’s always another email, another deadline, another appointment, another household responsibility, or another person who needs something.
And if you’re anything like me, you can probably invent seventeen additional tasks while completing the first one.
It’s a gift. And occasionally a curse.
One of the most important principles I’ve taken away from working with high-performing individuals is the value of treating rest as a legitimate calendar commitment.
Not a reward.
Not something you have to earn.
And certainly not the first thing you cancel when your week gets busy.
You actually have to schedule it. And then you have to honor your word to yourself.
Think about that for a second.
If you have a meeting scheduled with someone important, you make the time.
If you have a flight, you plan around it.
If your child has an appointment, you figure it out.
But when it comes to the time you’ve set aside for yourself, suddenly everything else takes priority.
Why?
Your personal time deserves the same consideration you give everyone else’s.
When I’m managing someone’s calendar, I want to know what restores them just as much as what demands their attention, because both deserve to be planned for. My job is to think ahead, anticipate your needs, and make sure the things that keep you feeling your best don’t get pushed aside when life gets busy. You shouldn’t have to remind yourself to rest, let alone remind me to make room for it. That’s part of what you’re trusting me to manage, and one less thing that should be on your plate.
And I’m not suggesting that every week needs to include a luxurious spa day, complete silence, and someone feeding you grapes.
Although, if that’s available to you, please enjoy it on behalf of the rest of us.
I’m talking about intentionally protecting time for recovery, even when life is busy.
Whether that’s a full day away from work, an afternoon without obligations, or a few hours where you’re not responsible for answering everyone else’s questions.
Start there.
Because effective time management isn’t simply about fitting more into your schedule.
It’s about being intentional with the time you already have.
Now, let’s talk about the systems.
The other two principles I want to cover are time management and strategic outsourcing.
And this is where my experience becomes especially useful.
I’ve spent years helping people organize the work behind their lives, whether that’s business operations, household responsibilities, travel, personal commitments, or the dozen small things nobody wants to deal with but somebody absolutely has to.
One of the tools I’ve continued coming back to is Trello.
If you’re unfamiliar, Trello is a project management platform that allows you to organize tasks, responsibilities, deadlines, and workflows.
I’ve used it in professional operations for years, and it’s evolved considerably with features involving AI, email integrations, calendar planning, and automation.
But here’s the thing.
You can have the world’s greatest software and still be completely disorganized.
Because a platform isn’t a strategy.
And outsourcing isn’t particularly helpful if you still have to personally manage every single step of whatever you’ve outsourced.
The real value comes from knowing how to build the system, where to create structure, what to automate, and what deserves your attention in the first place.
That’s the work I’ve spent more than a decade learning, practicing, and refining.
And that’s exactly what I want to make more accessible.
The JOAT Membership · Preview
A Preview: The Systems Behind the Success
You don’t need their bank accounts. You need a better operating system.
I’ve shared the thinking. Now I want to show you how I put it into practice.
Inside the private JOAT membership, I’m going deeper into the operational systems I’ve developed through years of supporting founders, executives, and high-net-worth households.
Including what I learned while helping implement a founder’s approach to time management after their Harvard executive education experience, and how I’ve since adapted those principles for other clients with completely different needs.
I’m not sharing anyone’s private calendar, confidential information, or personalized materials.
I’m sharing the knowledge, frameworks, tools, and processes I’ve developed from actually doing this work.
Here’s a preview of what we’re getting into:
- 01. Time Blocking + Trello
- 02. The Personal Operating System
- 03. AI, Email + Automation
- 04. Outsourcing Without Losing Control
- 05. The Tools, Templates + Habits
Exclusive Members-Only Access
This is where we get into the actual Trello configurations, step-by-step implementation processes, platform workflows, and the practical tools I’ve developed and adapted throughout my career.
Not just what these systems are, but how to build them, connect them, manage them, and make them work for your life.
Because, at the end of the day, you can be the most capable person in the room and still have absolutely no business being responsible for every single thing happening inside it.
The actual luxury?
Having your life run smoothly without having to personally run every part of it.
That’s what I’ve spent my career helping people accomplish.
And whether you’re managing a billion-dollar company, growing a business from your kitchen table, or simply trying to make it through the week without forgetting seventeen things, the principle is the same.
Doing everything yourself isn’t the flex you think it is.
Your time is valuable.
Start treating it that way.
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