Shoulda, Coulda, Woulda

Another framework for decision-making. A Lenny original™ developed during travels in Taiwan.

How to prioritize?

This was a conundrum that I faced for months, even years.

Balancing two jobs, side hustle, content creation, consistently writing, language learning, working out, traveling, and more caused me to feel constantly busy. Sometimes overwhelmed. Like there are not enough hours in a day.

I needed to simplify my life. But I couldn’t bear to part with anything. Every activity seemed important to me.

So before I resorted to sacrificing certain goals, I wanted to explore how to prioritize my tasks. For tax and security reasons, I wasn’t allowed to work my 9-5 while I was traveling in Taipei, so I suddenly had extra hours to think. With this additional time, I thought up a framework.

Welcome to the ‘should-could-would’ hierarchy:

1. Must [Needs]

2. Should [Obligations]

3. Could [Possibilities]

4. Would [Aspirations]

5. Do [Habits]

This is the order in which to ask yourself “what _____ I do?” Cumulatively, these categories should encompass every possible action or behavior that we engage in.

(The last category — Do [Habits]¹, as in “what do I do?” — does not technically need to be considered in our prioritization framework since, by definition, they do not require additional effort.)

1. What must I do? This category is for pure necessities. We need to drink water and eat food to survive. There’s not much else we absolutely must do. Virtually none of us have to actively prioritize this (if you’re reading this, you presumably have easy access to sustenance and shelter, etc), which is a great privilege. This is why we’re going to spend some more time talking about the following questions.

2. What should I do? Think hygiene. Academics. Career. These are obligations we have that are not immediately necessary for survival, but are pretty important in modern society. Even if we don’t lock these down, we’d likely continue to live — but drastically decrease our quality of life and chance of reproduction. It makes sense that we should prioritize these responsibilities over most other tasks.

3. What could I do? These are things that we might want to do, for a variety of reasons. Tasks that have some level of importance, but are not essential or critical to our lives. They may be beneficial to perform, but come at a cost of time, money, or energy. (Make sure to do the cost-benefit analysis.) Here, we have personal projects. Learning a skill. Reading a book. Keeping up with friends and family. Anything we desire to do which requires effort.

4. What would I do? Lastly, the aspirational category. This is the question of what we would do if we had near-infinite time and resources. These are things that we may not be able to do, but not reasonably justify doing in the near future. Whether that’s… Going on a yearlong meditation retreat. Becoming a full-time artist. Buying a new car.

You can prioritize further within each category. That way you have a clear order of operations for yourself.

Bonus tip: Easier said than done, but see if you can try turning your responsibilities into habits. Take steps to start doing them daily, more naturally, etc. Eventually it may become second nature. That way you no longer have to think about them!

Applied to myself, as of June 2025 (no need to read all this — it’s more for me than you):

1. Must

   1. Physical safety

   2. Food and water

2. Should

   1. Maintain mental health

   2. Fitness and hygiene

   3. Student loans

   4. Full-time job

   5. Part-time job

   6. Social life

   7. Chores

3. Could

   1. Read and write

   2. Go to temple

   3. Learn languages

   4. Create content

   5. Improve at chess

   6. Make music

   7. Draw or paint

4. Would

   1. Binge watch anime

   2. Start a business

   3. Found a nonprofit

   4. Explore the world

Now, I understood where my routine would create stress. Prioritizing ‘coulds’ over ‘shoulds’ or ‘woulds’ over ‘coulds’ — this is something I did often, and to my detriment. I clearly didn’t have my priorities straight. And now I have an easy reminder for what order I should do things in.

Playing chess to procrastinate at work? I knew intrinsically that something was wrong about it. But I didn’t have a conscious framework to understand the proper prioritization. No wonder that was anxiety-inducing.

So now I know. Before I can lock in on reading and writing, for example, I should make sure that I’ve done everything I need to regarding my health, fitness, jobs, chores, etc. Before I can think about starting a business or nonprofit, I should have done all the ‘coulds’ to reasonable satisfaction (as nothing is ever really finished.)

If you plan to implement this in your life, determine your framework thoughtfully. Know yourself. There’s nothing wrong with reassessing and reordering, by the way. Just make sure that once you have a solid idea of your order, follow it well.

Tl;dr: Prioritize needs, then obligations, then possibilities, then aspirations. What about habits? You’ll do them anyway, so don’t think too hard about it.

1. This varies from person to person, but by way of example, most of us scroll our phones as easily as we breathe. Like second nature. If you hope to a kick certain habit, that desire could be categorized as a ‘should,’ ‘could,’ or ‘would,’ depending on how important it is.