How to go from Dreamer to Doer

I’m a dreamer, always have been, always will be, but I’ve done a lot of doing. More than most people my age, which is a good metric to care about in a society that worships, fetishizes, and rewards doing. I’d like to share what I’ve learned that’s made me successful at getting stuff done in the past 8 years, but first, let’s distinguish dreamers and doers.

CotM feature Max Clarke GP

Connor’s Notes: Two things to know. One, this was inspired by an article¬†from Entrepreneur.com, which was shared by the¬†fairly successful young Matt Holmes. You might want to read through it, both because it’s good, and because it provides context for this post. Two, on a personal note, Max Clarke and I have known each other since college, and he might be the most successful of my college friends . . . a list which includes a growing cadre of doctors, lawyers, PhD. scientists, and so on. He is a largely self-taught software programmer who had the confidence to leave college to pursue his career, and the competence and drive to make that a sound financial and career decision. In other words, he is a smart guy, and sort of an authority on this subject.

How to go from Dreamer to Doer

I’m a dreamer, always have been, always will be, but I’ve done a lot of doing. More than most people my age, which is a good metric to care about in a society that worships, fetishizes, and rewards doing. I’d like to share what I’ve learned that’s made me successful at getting stuff done in the past 8 years, but first, let’s distinguish dreamers and doers.

A dreamer is someone who lives in a world of ideas. They collect and build cognitive tools that are in turn used to architect concepts. Often this work is a labor of love, and as such is not typically bound by time or the production of externally consumable artifacts, if any. A dreamer may have a journal with writing that only they understand, for example. Dreamers are less concerned with realizing a goal, and more interested in the discovery of what is possible.
Doers are driven by a feedback loop predicated on movement, and value speed, efficiency, and timeliness. Pursuit and completion are the rewards, so more and faster is better.
So how do I manifest ideas into reality? Here’s what I’ve learned so far.
View your tasks as projects.
The reason many projects never get done is because we vastly underestimate the amount of work required to make something. Even in the field of engineering, a field whose entire purpose is to solve problems, we tend to vastly underestimate. How would you complete this project if it were larger by a factor of ten? In software we multiply an estimate by pi (3ish because we’re human) to make sure our estimate is still reasonable. Remember that your estimate tends to include best-case, and we’re human. We have bad days, mess up, or find problems that we didn’t know existed while solving something that seems trivial, like buying the materials and finding out they won’t fit in your car, or that the door you thought was wood is actually aluminum, or finding that you’ll have to redo some complex wiring because your cat chewed through it.
Set aside time every day at the same time for a specific project.
There’s so much work that you can’t wait for the right time to complete it all in one Herculean effort. Failing to work often enough will also severely affect your ability to complete, because you’ll spend more time getting up to speed than actually making forward progress. You’ll find yourself picking up projects more often because you’re more familiar with them. It’s also easier to be ready to put in concerted effort if your days follow a predictable routine. DON’T put this time over needs time (like eating and sleeping, because scheduling over that stuff is exactly how you burn out and don’t get anything done).
If you are having trouble starting a project, break it down. Then break it down again.
Write a todo-list of that break-down. It should be specific enough that you can follow each todo and execute on it without thinking. If you could pick up that list next week and start up on it immediately without having to remember too hard the bigger picture of what you were doing, then you’ve done it correctly. Once you have a few more items than you can complete at one time (I usually don’t go above three major tasks, since more is over-planning), start the first task, finish it, cross it off, repeat.
Reality will never be as beautiful as the concept in your head.
Understand that you are biased, and want things a certain way for no reason other than beauty. If other people think it’s stupid, you might want to listen even if it’s painful. You’re here to get things done, and beauty is rarely efficient.
Find the fastest solution first.
Don’t commit to that solution, but ask if it supplies everything you need. Often dreamers (or maybe just me) over-engineer. An implemented solution is oftentimes a better solution than the best-case solution for getting things done. Don’t anticipate needs; maybes are not requirements. Get a second opinion from someone who is directly impacted by your decision.
Don’t lose the forest for the trees.
This is a corollary to the above: Don’t do everything yourself. Dreamers often get lost in the depth of something, and every task is backed by a rich discipline. Find the solution. Explore only out of need (though bookmarking interesting stuff to come back to later is a good habit). Cross off that task. You are here to do, so the dreaming will have to wait.
Different tasks require different types of efforts.
Some require more of the dreamer, others more of the doer. Be flexible in what you can provide so that you stay efficient. Sometimes being quick is slow. Follow the racing adage of “slow is smooth, smooth is fast”, but don’t let that keep you from making mistakes, or excuse you to dream when you should do.

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