I’m a serial over-thinker and a compulsive researcher (I fall victim to more rabbit holes than Alice In Wonderland). Whenever I need to take something more seriously, I come up with a challenge to guide me into action. A few days ago, I decided to do that for my writing.
I made a bet with my friend Kyle Bishop that I would write for 50 minutes a day for at least 60 of the next 90 days. I sent him $600 through the Cash App and asked him to pay me back $10 every day I wrote. Whatever is left at the end of 90 days, he’ll donate to charity.
I had just gotten back from four months of traveling, and I wanted to start writing again, but I struggled mightily to find the motivation to start.
On the first day of the challenge, I started writing for the first time in months. I whipped up ten article ideas and went cracking on the one that seemed juiciest. After ten minutes chugging along with that idea, I hit a creative block.
I jumped to the next idea. I chugged along for a few on the new idea, then I hit another creative block and jumped to another idea. After repeating this frantic pattern for a few more rounds, I finished my first writing session with a handful of barely finished drafts and outlines.
Great! I was writing again, but my process was extremely sporadic and lacked discipline. So, I narrowed the scope. I chose my favorite five article ideas, set an order to do them, and committed to Kyle that I’d write those five articles in that set order.
More, I resolved not to take on any other personal projects until finishing that commitment. It was a freeing decision. Until this challenge is over, I have no uncertainty about what to work on. My priorities are firm. I didn’t have a choice about what to do next and I loved it.
Consider a project with no due date, a writing assignment with no prompt, or an entire weekend without plans. These unbounded situations are supposed to be freeing, yet often are harder to operate within than something clearly defined like:
The situations are defined by a common problem: The Paradox of Choice.
The Paradox of Choice describes when circumstances with more options are worse (paradoxically).
In these situations, we frantically argue the merits of option A vs. option B vs. option C. Stressed about inconsequential details, we are stuck at the crossroads of indecision.
We quit too soon. We overthink. We do nothing.
Don’t let this be you.
The solution is simple: positive constraints.
I think of positive constraints as any rules or limitations that actually benefit a situation. Consider some examples:
A basic exercise to demonstrate constraints goes as follows.
If I asked you to tell me a joke, you’d likely fumble for a while trying to think of one. Instead, if I asked you to tell me a knock-knock joke, one should come to mind immediately.
The constraint, narrowing the type of joke, helps guide your tangled web of thoughts to a very specific body of knowledge: knock-knock jokes. Through the constraint, you arrive at answer quickly and don’t come off as the person with no jokes.
A positive constraint can be devised by imposing a fixed limit on an otherwise unbounded situation.
In high-school, I thought polos were the end-all-be-all of casual dress. By my senior year, I had accumulated obscene amounts of these shirts. Although your closet imposes a physical limit to how many clothes you have, I think it is best to be proactive and avoid hitting that point.
Desperate to reduce clutter, I imposed a rule: no more than 10 polos. How often did I need more than 10 unique polos within 1 laundry cycle? Never!
Other ideas include only owning a fixed amount of hangers (maybe 25) and letting that dictate your accumulation habits.
You can play with all types of variables such as how much time to give a task, how many choices to consider before making a decision, how many drinks to have before calling it a night (best decided before you go out), how many words to write for an article, how much time to spend researching versus doing. You get the picture.
In addition to manipulating quantities, thematic or qualitative limits can also be beneficial. Constraints in this fashion make one decision that helps to make thousands of future decisions.
Heuristics (rules of thumb) like this are a great simplifying force when applied correctly.
The most important concept to grasp from this article is that constraints make one decision that automatically simplifies thousands of future decisions. This plays out in two key ways.
If a decision isn’t constrained by a deadline, it is unclear how much time to give it. This conundrum affects people who earn $30 an hour but choose to spend five hours ($150) researching how to save $70 on flights.
These decisions are quantifiably not worth their time.
Give yourself a maximum time limit, or a maximum number of options to consider before deciding on the best you have seen.
Likewise, deadline pressure is a massive boost to productivity when working on a task or project. If I had an hour to submit a writing assignment I haven’t even started, I wouldn't lose focus if my house started burning down around me. Instead, if there is no deadline in sight, I’ll stare out my window at mosquitos and birds and contemplate the meaning of it all.
With no deadline for reaching a goal, I’ll read 10 books on entrepreneurship before taking real action and starting a project.
The question “is now the right time to take the next step?” lacks a clear answer.
By tightly constraining my time, I have no choice but to focus on what needs to be done.
The benefits of positive constraints are extremely similar to the arguments for Jocko Willink’s slogan “Discipline = Freedom.” In this framework, you apply extreme discipline to taking care of a few fundamental practices in your life such as sleep, relationships, learning, and exercise. From this discipline, you realize two major benefits.
Look at a few examples
Constrain situations and be disciplined in seeing to your priorities. Enjoy the freedom enabled by consistently living that lifestyle.
A few months back, YouTuber Matt D’Avella shared a great video called “The 3 Year Rule” where he described his thoughts on committing to projects.
When he decided to go full-time with his YouTube channel, he framed the decision as a clearly constrained experiment. Instead of haphazardly making videos for as long as he sustained motivation, seeing no results, and quitting out of disappointment, he resolved to work for two years and reassess at the end of that period.
Success or failure, he was going to make videos for those two years.
Neatly constraining his experiment helped push through periods of slow growth or lack of enthusiasm because of the clear commitment and reassurance that the project wasn’t forever. Besides, he could always go back to his previous line of work.
Results: He’s going on his third year and has 2.4 million subscribers.
When Tim Ferriss was exhausted from writing the 4-Hour Chef, he decided he wanted to try making a podcast.
He committed to recording six episodes and then re-evaluating. There’s a massive psychological difference between “starting a podcast” and “running a personal experiment” of publishing six episodes and seeing if he liked it.
Results: He’s gone on to make over 400 episodes, with over 400 million downloads.
These examples demonstrate the importance of constraining a personal project by defining a minimum amount of effort to put in before determining success or failure.
The idea that “less is more” gets tossed around all the time. The problem is that it is not very instructive. Most times I hear it, I look around the room I’m in, realize there’s some clutter, and proceed to do nothing about it.
Constraints, on the other hand, are practical ways to proactively apply the “less is more” mindset to any situation.
Consider reducing information overload, or “caging the monkey mind.”
Apply “less is more” to reduce mental chaos by limiting the number of inputs in your life.
Reduce the number of podcasts you subscribe to, the number of apps on your home screen, the number of social media platforms you use, the number of people you follow on a specific platform, or the number of habits you try to change at once.
The Pomodoro Technique is a way to leverage constraints every single day. Set a 25-minute timer to work solely on one task. For that 25 minute sprint, do not entertain any non-life-threatening distraction. Jot distracting thoughts on a piece of paper and explore them only at the end of the work session.
The timer presents a clear stopping point and pressure to work intensely. The clarity from the singular point of focus helps direct attention dramatically.
Unless I’m collaborating with other people, I do not do any serious work without a Pomodoro timer running.
So often, I have the feeling that I should be doing something productive, but without constraints, I get riddled with analysis paralysis and do nothing. Absent short term pressures like a looming deadline, financial stress, or a messy environment, I struggle to take action. I’ve realized that the more I can re-engineer situations using constraints, the more productive output I achieve.
It’s all an effort to run back to simplicity.
I challenge you to find a few areas to simplify your life. What are some positive constraints you could fashion to help make decisions, spur action, or prioritize? Be sure to tell someone about your constraints in order to have accountability. Accountability with a friend is the best way I know to reliably follow the constraints you set for yourself.
What one decision can you make today to decide thousands of future decisions?