I tried an unstructured life for a few months. No wake up time, no schedule, no commitment on deliverables. I was free to do anything I feel like doing. It seemed like the ideal state to be in, right?

I quickly realized though, this kind of lifestyle isn’t for me.

Day after day pass without anything meaningful happening. I had a list of things I wanted to do when I was super busy, but I have a lot of friction getting started.

My main issue turned out to be not having a structure.

I used to think being free means being able to do anything I want. It’s true. But what isn’t obvious is suddenly you have to decide on a lot things. Deciding on every single thing every day is mentally exhausting. “What am I going to do today? What time am I going to start? How much time should I spend on it?”

Pre-deciding is the key

A full-time job have a built-in structure. I wake up, take a shower, go to office. And in the office I have another set of routine to sit-down, identify what you need to do, do it until end of day.

This works because things are pre-decided for me. I didn’t have to think about it. I just have to follow it. That’s why it’s easier to do things.

I still don’t want the 9-5 lifestyle. It’s too rigid for me. What I end up copying is only pre-deciding on things. I start each week with a weekly planning where I check my calendar with upcoming commitments. I then list things I have to deliver within the week and arbitrarily put them any day depending on when it’s expected.

This significantly reduced the friction on how I start my day. Because it was pre-decided already. I just have to sit down and do it.

Structure sets me free in a way I don’t have to think of what I need to do everyday.

Put me in a bad situation and I’ll find a way to blame it on myself. Be it lack of action, lack of insight, or lack of preparedness.

This isn’t some self-pity indulgence. It’s more of putting myself in a position where I could do something.

Imagine the alternative: blaming it on another person. What I’m doing here is just unloading an unwanted feeling to another person. How the other person will react is out of my control. Most likely, nothing is going to change.

Putting the blame on myself let me focus on things I could have done instead. Learn from it and apply it to similar situations moving forward.

Do this only if you have a healthy sense of self-awareness

Lately, I realized that this is only applicable if a person have a healthy sense of self-awareness. There’s a thin line between this and “everything is my fault” attitude.

The key difference is knowing deep down that any mistake is not tied to one’s being. Simply put even if I failed on certain things, I’m not a failure. That’s not how human works. I know that a single failure couldn’t possibly define my whole being.

With this mindset, I’m always forward looking. I see failures as learning opportunities. I don’t feel helpless.

Rather, the discomfort I feel blaming myself is similar to the discomfort I feel when lifting weights. Both increases my capacity. Mental capacity with the former, physical capacity with the latter.

I heard the idea “fake it till you make it” back in college. I tried it a few times. But every time I do, something always felt off. The whole interaction that comes after is usually stressful. I put myself in a position where I have to be careful with my words, where I can’t be fully myself, or share challenges I encounter with what I have to deliver.

It’s a big disservice to the other person because expectations were not properly managed. If they knew I couldn’t do certain tasks, they could’ve tap other people to do the work instead.

Beyond this, faking doesn’t align with my values. I value truthfulness (even if it hurts). If I don’t practice it myself, how can I expect other people to do the same? This incongruence with how I want to live versus how I’m living makes me uneasy. It’s essentially lying to myself.

A better alternative: face it till you make it

The way I approach it now is saying what I’m lacking upfront. I’m straightforward with things I don’t know. I’m more willing to appear like a fool now. No one is expert on everything anyway.

I lay all my cards. I share what I’m good at and how can I help them achieve their goals. I share my plan on how I’ll address my lack of skills.

It’s a risk if they want to continue to work with me. But it’s a risk they can decide for themselves. The other person can make an informed decision.

If they do decide to go ahead, I’d be grateful for the trust. I’d go extra mile to deliver what they need. If not, that’s okay. There are countless other people. I just need to match with people that will benefit with my current expertise.