Planned Freedom

Jonathan Choi
Escapement Blog
Published in
5 min readJul 15, 2019

An oxymoron

While planned freedom sounds like an oxymoron, the two actually share more similarities than differences. We like to think that by not having a plan, we can be spontaneous and hence be free to do what we like when we like it. But is that really true? Freedom is “The state of not being subject to or affected by (something undesirable)”, so it is important to understand what the undesirable thing is. Can we really say that having a plan is undesirable? And are we really enjoying the freedom when we are free from the restrictiveness of a plan?

Photo by Nathan McBride on Unsplash

I think the concept of spontaneity is misunderstood and we are mistaking the lack of planning and commitment for freedom. By keeping our options open, we are actually limiting what we can do. We all have a limited amount of time and with more and more things demanding our attention, we need to prioritize diligently so that we can really be free to do what we want to do.

It is a false dichotomy to think that planning and freedom cannot coexist. I believe we actually need to plan more in order to truly be free. While planning doesn’t sound like the most exciting thing you can do, the planning process is one that can really enable us to understand our priorities and help us achieve freedom.

Why freedom isn’t as free as you think?

The modern world is full of abundance, with endless content to consume, events to attend and people to meet. It certainly seems like we have more freedom to decide what we want to do, but is that really the case? Having lots of options creates an illusion of freedom but in reality it hinders our ability to act. Paradox of choice is the theory that describes why having more choices can lead to negative effects. While the study focuses on consumer choices, a similar concept can apply to us making decisions on how we decide to spend our time everyday. Regardless of the amount of choices we have, we all face the same constraint that we only have 24 hours in a day. The increase in options adds to our cognitive load and we end up spending more time deciding what to do rather than doing the things we want. These options end up distracting us from what is important rather than providing us with good alternatives.

So what can we do to take advantage of the abundance of options rather than be beholden to it? Prioritization is the key skill that can enable us to take control of how we spend our time and ensure that we are really achieving freedom rather than just the feeling of it. As more and more distractions creep into our options, we must learn to prioritize diligently. Prioritizing is not easy because it requires us to make decisions and by saying yes to something, we need to be saying no to others. Although it might seem easier to cave in and not prioritize, it is not a smart strategy because we are implicitly letting other people take control of our time. The most difficult part about prioritization is to be honest with ourselves and acknowledge what is important to us and be brave enough to choose what we really want to do.

How to plan for freedom?

Planning is a good way for us to take control of our time and make decisions on how we should be spending it. Planning is difficult and we often fail to execute, even if we have a plan, but it is still a better option than not having one. A plan doesn’t need to be restrictive, a plan just needs to be honest. Here are a few things that we need in order to plan effectively:

  • Constraints can come in many different forms like deadlines, dependencies and limited resources. They form the boundaries that we operate in and we need to decide carefully what is really a constraint for us. While constraints might seem limiting, they can be a great motivator when combined with the right ambition. Also, when we understand the constraints well, we can start to find ways to challenge and improve them, to create more space for ourselves.
  • Priorities drive our decision making process as they represent what is important to us. We need to have priorities that resonate with us personally because it is our time we are spending. They will form the guiding principles that we use to pick one commitment over another. While external influences can change the constraints we operate in, they should not have any influence on our priorities.
  • Self Awareness is what makes a plan work. The planning fallacy shows how bad we are at planning but it is a situation that can be improved. If we can practice to be more aware of how much time we need and whether we can realistically achieve the plan, we will be able to come up with feasible plans that will empower us to be free.

Once we have a clear idea of the above, we can start to plan what we want to do. Now you might be thinking that this doesn’t sound like freedom at all and I can understand why you would think that. While it might be easy to take a day off and do whatever comes to mind without all this hassle, it is significantly more difficult if we want to be free in the long run. The effort we put in to planning will pay off many times over when we truly get to enjoy the freedom and live in the moment. We can afford not to worry about what comes next and about other responsibilities because we have planned this freedom.

Tough Decisions

At the end of the day, we only have a limited amount of time to spend on what is important to us. I hope we can all start realizing that we have ultimate control over how our time and energy is spent and start making decisions to do what we want to do. We will have some tough decisions to make but the cost of not making them is way too high. Like any habit, we need to start small and stay consistent. We don’t need any tools or frameworks to start, all we need is to start by asking ourselves what is important to us and have the courage to say no to other distractions.

With this new understanding, we should revisit our original question, what is really the undesirable thing that we want to be free from? There are many different answers to this question, but I hope you will stop thinking that having a plan is one of them.

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Jonathan Choi
Escapement Blog

Passionate about living a meaningful life. I write about productivity, work life and data.