Too Much to Do...//Organize

Have you ever been to a sweat lodge or a sauna? I used to go pretty often when I was younger...a sort of family tradition every Friday which I grew to love. Did I like it at first? Not really. The concept of sitting in a hot box for a prolonged period of time for the purposes of sweating wasn't something that I completely understood. After doing it the first few times, I grew to enjoy it, and understood the health benefits, which made me enjoy it even more. The more I went, the faster my body would react. Within a year or so, my body became conditioned to react to the stimulus of heat very quickly.

Thankfully,the purpose of this post is not to let you know about how one would shvitz. The purpose of this is to share a little bit of insight from running a startup that undoubtedly any founder will run into at some point in their journey: being overwhelmed. We are creatures of habit. The more we do a particular thing, the more we are likely to continue doing it. If this thing is positive, it has a positive spiral effect. Unfortunately, this works the opposite direction as well. Just in the same way that our bodies can be physically manipulated to respond more quickly to specific stimuli, we invariably force ourselves into habits through repetition.

We become that which we do. The more you repeat, the better you get.

In the world of startups, we find ourselves bombarded with a never-ending list of "shit to do", broken down into our choice of an organizational app/notebook. But at a certain point in time, things pile up to the extent that prioritization is limited to that which is right in front of our noses. This tunnel vision is great to accomplish those specific deliverables, whether it be putting together a new sales comp structure, on-boarding materials, compiling a new enterprise pitch deck, structuring a product development roadmap, etc. But as soon as the next thing is placed in front of us, whether it be by ourselves, our clients, our team or our investors, that will take the new priority. Sooner or later, the small things mix with the big things, the strategic thinking with the operational, resulting in an alphabet soup of things to do, and an ever increasing level of being overwhelmed. So we crash and reset. For me, a crash would entail a weekend of responding to emails on my phone, binge watching a show for 3 hours, then feeling useless and getting back to my computer to get back to work, followed by making dinner and having a drink of sorts, then a book, or movie, or anything that would help me get my mind to disconnect...just for a little.

Very quickly, we see how this non-stop barrage of little deliverables can easily turn into a much bigger problem of constant re-prioritization and a lack of focus.

This consistent flow of seemingly small things can easily bottleneck your own productivity and focus.

Fail Fast

Was it productive to take that time off and watch a show or read something off topic? At the time, it was the best option I could come up with. The weekend was less productive, but the result was that I could now get back to work with a clear mind and a reset compass of priorities. So I went through these phases of crash, reset and get back to work, which happened every 2 months or so. This became my natural ebb and flow. But it was not beneficial. There had to be a better way, which got me thinking: fail fast.

By that, I don't mean that you should go through these crashes, but instead, set up a regular protocol to reset, and organize it. Instead of waiting for 2 or 3 months when a crash was imminent, I started to set aside time in the evening and the early morning to check on my list of deliverables, and prioritize them based off of what was in front of me (normally operations/sales/marketing), as well as what I knew needed to get done in the short/mid-term, such as compiling new decks, or getting ready for the next batch of sales hires.

I like to keep a notebook where I have three sections on there right and an open page for notes on the left. The right page I jot down thee important tasks for each section. The left page is for lesser priority; things I should be doing that are of less importance or are tasks too big to complete all at once. (Below, I added a section which will show you another methodology that I found immensely helpful.)

Eating an Elephant 1 Bite at a Time

Building a startup is like eating an elephant...so do it 1 bite at a time. Take your big tasks, and break them into smaller tasks. Then take those smaller tasks and break them down until you have a set of manageable tasks to complete. Take the Pomodoro Effect as a model, where you set 25-30 minutes to focus on something and get it done, after which your focus will start to wander. Follow this rule of thumb: 30 minutes to focus, and a few minutes to do other things, like checking emails, answering calls, Slacking team members, etc. You get the point.

I will be compiling a list of books that founders and go-getters should read for future refernce. In the meantime, there are good snippets of information in Peter Drucker's The Effective Executive.

Reset Often

Before you go to sleep, take your notebook/phone/computer, and go through that checklist you compiled to see what was in fact completed, as well as what has yet to be scheduled. If you see that things on the "right side" are not finished, then you either did not allocate enough time to focus, or the tasks have not been broken down into manageable pieces.

i.e. Writing "Create Deck for Sales" is NOT a good set task. I mean it's a start, but it can be better. Instead, break it down into its appropriate pieces, and set them as their own tasks:

Sales Deck

  1. Intro to the company and why you should care
  2. Case Studies and other happy customers
  3. Specifics around what next
  4. CTA! Make it customizable for each sales person

Make it Work

Obviously each one of us has our preferred method of managing our daily tasks, but you won't know which your most predictive method will be until you try several. And the best way to start is to start somewhere. You can try my model, or schedule your day Pomodoro-style (Free Pomodoro Timer: http://tomato-timer.com/) . Ryder Carroll has done an amazing job at putting together an analog tracking methodology called the Bullet Journal. Take 15 minutes and check it out.

Now go and do. At this point in time, it doesn't matter how you start, so long as you do something. Seriously...stop reading this and do something. You have enough shit to do...prioritize and keep hustling. Just hustle smarter and faster.


As a founder, an entrepreneur and an individual driven to succeed, you cannot afford to break down, at least not publicly. Your company has to believe in the future, regardless of what is going on in your mind. Such is the burden of being a founder. Never lose sight of the big picture, and never stop hustling (from my previous post). When you make it, everything will have been worth it.

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