I never thought I would be considered an organized person.

You might not guess this about me, but I was disorganized for most of my life. This disorganization wasn’t just confined to an inconsistent schedule day-to-day. It spilled over into my long-term planning, manifesting itself everywhere from my messy desk and bedroom to my bank account.

When I was working on my first startup after graduating in 2015, I remember when my uncle Brown told me to “put in an adaptable roadmap.” Essentially, I needed a plan to get all the way from A to Z.

This wasn’t as simple as it sounds at all. Just the thought of creating an entire “roadmap” felt daunting and overwhelming.

At the time, I could barely plan out a full day by myself. How could I do it for a business? Wasn’t everything supposed to magically fall in place on its own? Wasn’t it supposed to be the same for personal relationships?

Starting the Journey From Chaos to Organized Excellence

For a couple of years, I was blindly stumbling around without ever really figuring this out. I spent most of 2018 and 2019 establishing my core “foundation.” I’m not kidding! It has literally taken me two years to form “healthy habits” and put systems in place that yield the results I want to achieve.

I have specific systems for taking care of all the critical aspects of my life:

  • Health
  • Personal relationships
  • Finances
  • Work

In this overview, I’ve broken down all the in’s and outs of my organizational systems from both a personal and professional standpoint. This is only part one, so I’ve primarily focused on health and work.

I hope having this document to add to your toolkit will help expedite the process if you decide to do the same for yourself.

Before I dive in, I want to preface all of this with a simple thought: it’s most helpful to visualize how every part of your life fits into specific buckets.

My coach calls this mental exercise finding the “items within the lines that deserve full focus.” Just like would on a basketball court, ignore everything outside of these lines like screaming fans for your opposing team: they just don’t matter.

Secondly, take every item between the lines and plan them out in detail:

  • Three months out
  • Weekly goals
  • Daily plans
  • Yearly (if you’re super advanced)Being relentlessly focused on the proper review and analysis is what enables me to iterate.


Using Google OKRs for Quarterly Business

I use quarterly OKRs to sort everything in my business into three specific buckets:

  1. Systemization & Operations
  2. Marketing & PR
  3. Business Development

I break each of these quarterly goals down based on where I want the business to be a few years out. Conducting a Vivid Vision Exercise has always given me a ton of clarity to find and follow my “North Star.”

At the end of each quarter, I conduct a review of the quarterly goals I set. Assessing performance regularly this way helps me refine my strategy. Based on what worked well and what didn’t during the last three months, I make a data-driven plan for the next quarter.

Here are a few examples from my OKR Doc:

Recap Quarterly Reviews in Aggregate

It’s easy to get too far into the weeds focusing on what didn’t go well. If you take a holistic view instead, you can see how far you’ve come.

From this review process, I then made my next set of goals for the different buckets within the business stated above.


Now, it’s time to plan each week.

I often look at the week, and round up what needs to get done, and then send an email to the team, based on who needs to do what based on priorities.

This document serves as a great reference for me throughout the week to make sure I’m staying on track. It also helps me work with the team to do the same.

Devils in the Detail

Now you have quarterly and weekly goals, how will you plan the day-to-day?

Deciding what to do first is often the most challenging step.

Before I dive in, I want to highlight three books that have been incredibly beneficial resources for structuring my days better and team operational performance to sustain our daily success:

WHEN by Dan Pink 

Indistractable by Nir Eyal

Activators by Mark Green

The Fast Forward Mindset by David Schurnman

In WHEN, Dan Pink lays out the best times of the day to do specific tasks based on how we perform at different levels.Every morning, I spend from 6:30 AM – 8:30 AM focusing on the 1-2 most important tasks for the day. This might pertain to client strategy, writing newsletters and articles, and planning overarching company goals.

I need a fresh mind for each of these items, and there are usually no distractions in the early morning. Most people are just getting the day started or even still asleep. This time period is also a great opportunity to block off important calendar events.

I generally workout either around 9:30 – 10:00 AM or 3 PM (I’ll get more into how I take care of my health later).

During the afternoons, I’m usually taking phone calls, in meetings with clients or my team, or doing podcast interviews. From 12:00 PM – 4:00 PM is my time block for tasks that don’t require a ton of “brain energy.” This period helps me stay fresh. If I was mentally sprinting from 8 AM – 3 PM, I would get burnt out.

I conserve energy by scheduling tasks based on the time of day that’s most optimal. Sometimes I nap or work out between 3:00 PM – 5:30 PM, and I try to eat dinner before 8 PM.

In the evenings, I spend from 8:30 PM – 10:30 PM doing creative and more heads down exercises. Nights are a sacred time for me, similar to the morning. This is often when I have lightbulb moments that inspire the “creative genius” which Allen Gannet describes in his book, The Creative Curve.

At night, I don’t need to be as “on” or intensely focused and alert. My subconscious gets more in motion, which makes this the best time for creative exercises like writing.

I’ve found this schedule to be the most effective daily routine for when I do tasks. Lastly, I try to go to bed around 11 PM and up by 7 AM.

On Saturdays I try to take the entire day off for a brain break to come down from the week. I spend these days hiking, reading, sleeping, and having fun with my girlfriend for the most part.

I find crowded environments where I’m forced to talk really suck the life out of me when I’m already beat down from the week, so I try to avoid situations where I am going to have to be alert.

On Sundays, I come back online around 3:00 PM – 4:00 PM and start preparing for the week.

Note: I’ve been tweaking this system for the past 8 months, but have found it to be highly effective so far.

Within each day, I’ve been using another system to manage my tasks every 24 hours. I write out my daily task between 3 and 4 times a day. If this sounds like a lot, it’s worth it. Trust me, there is no better feeling than crossing off line items for what you need to get done.

Here’s what mine looks like:

On the left side, under big-picture goals, I write the top 3 tasks or goals (my morning goals). I’m writing this article right now as we speak, so I promise this isn’t fabrication.

On the right hand side, I write out all my tasks and rank them based on what I need to get done. If I get the top 4-5 tasks done for the day, I consider it a great day.

That is how real progress is made. Sometimes, I write this out 2-3x a day on 2-3 pages. When I rewrite my tasks, it’s almost a way for me to stay mentally refreshed and organized. As I like to say, “it keeps the day in front of me.”


At the beginning of this year in January 2019, I was 6 months removed from shoulder surgery. Physical therapy was horrific. Every time I looked in the mirror, I was disappointed. I wondered every day; “Will I ever be in decent shape again?”

A couple months into the year, I stepped on the scale and it read “217 pounds.” For a 6”1 guy like me, you might just think, “Bryan is just really strong.” Being honest with myself, though, I knew I didn’t like how I looked in the mirror, and I wasn’t feeling my best mentally about it.

My typical weight is 190, which gives me a nice lean figure, and I was 27 pounds more than I wanted to be. The stereotypes are wrong! Men can feel bad about their body image, too.

I knew it was time for change, and change indeed. Here is what I started doing:

  1. Personal Training: I started seeing a personal trainer 2x/week. We work primarily on rehabilitating my shoulder and upper body (which we are still doing – shoulder surgeries suck).On my off days, I spent time doing conditioning on my own. Running, swimming, biking, etc. I found this has been an effective way to keep my heartrate up when I’m not actively challenging myself during a high intensity and strength based workouts.
  2. Dieting & Intermittent Fasting: I also started listening to a podcast called Burn It Nutrition. It was incredibly eye-opening thinking about this concept. First, I cut mostly all grains/breads, alcohol, and sugars (except on Saturday when Georgia plays). This diet change alone helped  me drop at least 15 pounds. Here is a great link about intermittent fasting! From there, I started implementing different times of the day that I ate – similar to when I worked out. I stopped eating breakfast (especially oatmeal loaded with berries, peanut butter). This kind of meal is a lot for the body to digest. I only drink coffee to expedite my metabolism and cognitive speed.  I wait until 11 AM or noon to eat lunch, and try to stick to a heavy, protein-based meal with few carbs. Lean proteins like aggs, meat, and chicken are my go-to’s. In the afternoon, I get hungry again, and I try to stick to protein bars, fruits, cliff bars, etc. Sometimes I take a cookie, but maybe 1x/week. Having a light snack in the afternoon keeps my energy high. For dinner, I try to do fish or meat, and stay away from heavy pastas and desserts.

From my recent LinkedIn post:

3. Mental Health: I work with a therapist 2x/month. This is really helpful. He specializes in behavioral health, and human performance. Beyond just listening to me, he gives me the tools to stay on track throughout my day. I’ve been working with him for 10 years, through sports, the startup journey of not having it going how I wanted, and growing our business.

This is imperative for me to keep and stay on track with. It’s something I never just “remove” from the calendar. I also find going when I don’t want to are always my best sessions.

The one area of my life that I still need to put in frameworks is my finances. The business account, payments, and everything else have all been combined in my personal account. While I have a good system for write-offs, how I pay the team, it’s extremely clunky, and still at version 2.0. Of 5.0 that I envision in a few months.

It’s sometimes hard for me to see and plan financially when I have everything mixed together. As the business becomes an LLC, and we finally put in a business bank account, payment system, auto invoice system, and ability to receive payments under one unified system, I think I’ll be able to breathe easier in this department, save for longer term goals personally, and understand where my money is going “outside the business’. My financial situation right now used to resemble every other area of my life …

… but I’ve learned that having an effective process is like compound interest. The more you do it, the more you see results – consistently. It also leads to more confidence, because when you get a “big break” it doesn’t feel like “luck” but rather, a result of good process that you put into your life to achieve the things you wanted or have the right things fall into your lap.

I’ve also implemented systems into my personal relationships for when I see my family, etc., but I figured for this audience, health and business systems might be the most relevant. I hope this article helps and maybe I’ll return in a few months when I have finances figured out more thoroughly and systematically. Stay tuned for more on that in the next part of this series!