What does “freedom” mean to you? Do you consider yourself free? Which freedom are you working towards?

Not exactly sure?

Let’s talk about two common visions of freedom:

Freedom #1 —

Buy a camper van, drive it west (or east, or north, or south), live like a gypsy. Do what you want, when you want, without being anchored to one job or one place.

Freedom #2 —

Get proactive and earn some serious coin. Travel the world luxuriously. Buy anything you want. Spend your time with important, glamorous people.

“Sign me up” you say?

Okay, which one would you prefer?

Let’s weigh the pros and cons:

The pros of freedom #1 —

Low cost. Experience beautiful places. Meet interesting people. Looks great on Instagram.

The pros of freedom #2 —

Not stressed by money. Experience beautiful places. Meet interesting people. Looks great on Instagram.

The cons of freedom #1 —

Reliant on odd jobs or residual savings for income. Lack of domestic comforts. If the van breaks down, you may become location restricted. Treated as a criminal vagrant in places where camping is unwelcome.

The cons of freedom #2 —

Could take years or decades to earn your wealth, requiring constant sacrifices of your time, energy, and desires. Anchored to your contacts, your commitments, your investments, etc.

left: instagram.com/chandra.rae | right: instagram.com/tomclaeren

The flaws in this article so far —

These aren’t your only options. What about digital nomads who work abroad in exotic destinations with minimal living expense? What about “trust fund babies” born to freedom #2 without having to work for it? What if the camper van gypsy made a clever investment that fuels their lifestyle with passive income?

What if you don’t care about travelling, or meeting people, or spreading FOMO on Instagram? What if your freedom is a repetitive suburban life without troublesome variables?

Let’s jump back to the initial question:

What does freedom mean to you?

I can’t predict your answer but I believe I can predict the thought process you’d use to come up with it.

Like postage, freedom comes with a “to” and a “from”.

You want the freedom to: sleep on the beach, wake up in a different place every day, buy fancy things, eat what you want, etc.

You want to be free from: a 9–5 job, your mortgage, deadlines, restrictions on your dress and speech, etc.

One aspect of freedom is additive. You’d like to do and have awesome things.

The other aspect is subtractive. You’d like to be free of stuff you hate.

Freedom is compromise —

To/from, add/subtract, however you conceptualize it, your definition of freedom represents a compromise between these desires.

If you’d like the freedom to buy things but you’d also like the freedom from a demanding job, you need to compromise.

If you’d like the freedom to eat delicious things but you’d also like the freedom to run 10 miles without winding yourself (aka freedom from poor fitness), you need to compromise.

Which freedom do you want most and how do you plan to get it?


Freedom is rules —

Counterintuitively, planning freedom looks a lot like creating constraints, or setting rules for yourself.

I was FaceTiming my mom recently and mentioned that I’d spent the past two weeks working on one project despite an upcoming deadline for another project. Work on the first project has been spontaneous and enjoyable. The deadline for the second project is self-imposed to honour a promise I made to myself months ago.

She said, “[The first project] sounds like a good idea. Why don’t you keep doing that?”

To which I replied, “Because I promised myself I’d finish [the second project] by [arbitrary self-imposed deadline] and I need to keep my promise to myself.”

She sighed, “You and your rules.”

Me and my rules? Hmm. I do seem to have a lot of them.

For example, I love pizza, chicken wings, and ice cream, but I want to be fit so I eat a low carb, low sugar, vegetable-centric diet from Monday to Friday — no pizza, wings, or ice cream allowed. Likewise, it’s because I love alcohol that I don’t allow myself to drink it on weekdays.

These rules don’t feel like rules, though. Following them is sometimes difficult but typically enjoyable. Why is that?

Apologies if this image offends you.

The control:constraint ratio —

Freedom, which appears to be a fairly abstract idea, must be more of a feeling than a circumstance. How free we feel is how free we are, though this feeling is obviously influenced by our circumstances.

The feeling of freedom is a feeling of control. What percentage of your life do you feel you have control over? What percentage of your life is constrained? I suspect there’s an optimal baseline ratio — maybe 70:30 in favour of control — which results in the average person feeling happy and free.

Let’s say you hate every second of your 9–5 job. That’s one third of every 24 hours lived against your will, leaving you with a maximum of 66.66% of your life to claim control over. If you don’t enjoy sleeping and view it as wasted time, eight hours of sleep are another third of your day which you don’t control, leaving you with only 33.33% of your life to claim control over. Sacrifice at least one third of that time to tedious chores and obligations, and you’re left with 22.22% — approximately one fifth — of your life which feels within your control.

That’s a 20:80 control:constraint ratio. Not ideal.

Now, let’s say you mostly enjoy your 9–5. On average, you would only choose to be elsewhere for two of those eight hours. You look forward to eight hours of restful sleep and the interesting dreams which accompany them. A third of your non-working, non-sleeping time is given to chores and obligations which you happily complete because they make you feel useful and engaged. Besides those two hours near the end of the work day when you’re ready to pack up and go, you have a general feeling of control over 22 hours each day. That’s 91.66% of your life which feels within your control.

That’s a 90:10 control:constraint ratio. Nice!

Who do you think is happier, 20:80 or 90:10? Which one is more free?

Of course, this example is flawed because it places two versions of you in identical circumstances where the only difference is your perception. In reality, your circumstances are influenced by your choices and actions, giving you the power of accountability.

How do you choose to be a 90:10 person?

Choosing freedom by choosing your constraints—

I think the first step is acceptance. Accept that every desire is accompanied by sacrifice and it’s not our destiny to get everything we want. Fame comes at the sacrifice of privacy. Fitness comes at the sacrifice of McDonalds. Anything you choose to do comes at the sacrifice of time you could spend doing anything else.

The second step is probably making a two column list, “Freedom to” and “Freedom from”, containing the things you definitely do and don’t want in your life, respectively.

*Note: start small to keep it simple, maybe 5 items per side.

Next, you could make another two column list, “Freedoms” and “Constraints”. The freedoms column contains all of the freedoms you wrote down in the previous list and in the constraints column you write down the challenges you associate with each freedom.

Now comes the moment of reckoning. Add a third column to the list, labeled “Compromises”. Slowly descend the constraints column, contemplating each item. How could you overcome the constraint? Write down the best compromise you can think of.

Some compromises will flow from the fingers. You’ll neatly lay down a plan to earn the freedom you desire. Others will feel forced and unbearable.

If the compromises seem unbearable, their associated freedom probably isn’t a freedom at all. How much you want something will always determine how much you’re willing to sacrifice for it, but my guess is you’ll benefit most by pursuing the greatest freedoms with the most manageable constraints.

What’s important is that you’re being honest with yourself about what you’re willing to do and sacrifice. The constraints you choose feel a lot like the freedoms they represent.

When it’s Tuesday night and I’m eating something which in no way resembles pizza, I’m okay with that because I love my healthy body and I especially love my Sunday pizza. If giving up pizza was unbearable to me, I’d be forced to sacrifice my healthy body. Either way, it’s my conscious choice.

And choice is freedom.

If you’d like to try the exercise, you can access the worksheet here and click File > Make a copy