How to Keep an Organized Startup in a Messy World

Life is a messy business. And there’s no cleaning it up. Two reasons being:

  1. It’s simply impossible.
  2. It’s supposed to be this way.

I am reasonably certain that a completely sanitized and predictable life is sub-optimal for human flourishing. That said, there are some areas of our lives that will run much better with some degree of organization and planning. Yes, when we plan, the universe laughs. We can’t win all the battles. But if we are very strategic, we can win a few important ones.

When it comes to startups, planning and organization is one of the keys to success. The better organized a startup is, the better equipped it will be to handle the winds of chaos that will inevitably come. You can’t win every battle. But here are a few worth fighting:


Time Flies; So Clip Its Wings

We all have plans. No one goes through life without a rough idea of where they are headed, at least in broad strokes. Yet when our general plans do not come to fruition, we lament the fact that time just slipped away from us. It is as if we cannot predict time.

As it happens, time is the most predictable thing in the universe, at least on our scale of experience. We know exactly how many seconds are in a day, a week, a month, a year. We know exactly how much time certain tasks take to complete. We know how much time it takes to get from one place to another. We can even predict our arrival times despite variables such as traffic. Compared to the lower animals, we are temporal gods, the masters of time.

So it is highly suspect that when the time comes for us to get work done, we suddenly have no clue about how time works. The problem is not time. It is the fact that we do not take our work seriously enough. If we did, we would plan accordingly.

The worst planners in the world are grade-school students. Yes, they are even worse than entrepreneurs. Yet many students have found time management possible, and even fun with highly customized, printed planners from sites like

There are other advanced tools for business people who live by the axiom, “Time is money”. If a day planner can help students remember where their next class is, what assignments they have, and what blocks of time they have to complete those assignments, surely small business owners can find similar aids to help them clip the wings of time.


Digitize Everything

Obviously, you are going to itemize your taxes. How else are you going to completely write off that super sleek, 12” Macbook? While you’re at it, you just as well try to stick the government for the tab on the lunch you had with a business buddy last week. (This is not tax advice. See your accountant.)

Thing is, when the IRS comes knocking with a few questions about some of the more questionable expenses, they are going to want to see some receipts. Can you lay your hand on that car rental invoice from two months ago? Even if you have it in a shoebox somewhere, if you can’t find it when you need it, it is like not having it at all. Use scanning software and apps to digitize everything for later retrieval from a searchable archive.

Keep Business and Personal Separate

You drove your car to pick up a client and show a property. After that adventure, you decide to go to the store and do some shopping for the house since you are already out. One is a business use of the car. The other is not. If your records cannot clearly distinguish between the two, then you are not ready for business. Many milage tracker apps abound in all relevant app repositories. Find one you like, and use it.

Into every startup, a little chaos must fall. But you can survive and thrive with a little planning and organization.


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