I can’t regret a burger right? Especially In-N-Out?!

I can’t regret a burger right? Especially In-N-Out?!

I wrapped up my last post mentioning how I’ve made a lot of bad decisions. The typical feeling associated with these decisions is regret. The question I’ve been thinking a lot about lately is how to discern between the different types of regret I can feel, and what is the best way to handle it.

Revisiting a decision

A key part about decision-making is that I have a certain amount of information available to me at the time of the decision. For example, I could bet on a specific stock if I’m impressed with what the vision and current progress of the respective company is.

After making this decision, a number of things could happen:

  • The stock skyrockets, in line with my assumptions

  • The stock skyrockets, in ways I could not have foreseen

  • The stock plummets, contrary to my hypothesis

  • The stock plummets, in ways I could not have foreseen

Whether the stock goes up or down, if it was unpredictable given the knowledge I had at the time, then I (should) feel confident that I made the right decision. In contrast, if the stock performs outside of my expectations, whether up or down, I can start to question whether the decision was a right one.

Revisiting that decision involves a frank discussion with myself about what I should / shouldn’t have known at the time of making the decision. As I mentioned in this post, if I put a good amount of thought and effort into picking a stock, that in itself should make me comfortable regardless of the outcome.

The challenge here is forcing myself to revisit decisions I make, regardless of the outcome. If the stock went up in ways I didn’t predict, the outcome is in line with what I want, so I won’t question whether the decision was a good one. Though realistically, that lack of questioning might lead me to make an even riskier decision down the road, using the same (probably flawed) line of thinking, that ends up hurting me a lot more.

Forceful re-evaluation

With those scenarios in mind, it’s clear that decisions can be bad ones if they are not revisited. However what makes me want to revisit a decision in the first place? Regret.

Regret is an emotion that is often sparked by the outcome of the decision, but can be associated with the decision itself and/or the outcome. I wouldn’t regret going to the gym unless I hurt myself, nor would I regret playing video games unless I had something pressing to do.

So I can accept that there will be decisions that I make in error; specifically where I don’t consider all the possible factors and end up choosing the wrong option. That’s life, and I’ll learn from those decisions.

What frustrates me the most, is feeling regret from decisions that I am / was very confident in making. Ones that I put an incredible amount of thought into, got insight from people I trusted, and gave it time to ensure I wasn’t making any impulse decisions.

This is what I would call ‘regret from outcome’. Leaving San Francisco is a primary example of this for me. I miss the work, the people, and (sometimes) the city, and that can make me wonder whether it was a regrettable decision. However, I’m still confident in the logic behind the decision and the process I went through to get there.

Handling regret

So what exactly should I do with ‘regret from outcome’? It’s purely emotional, and I can’t exactly logic myself out of it (trust me, I’ve tried). I’ve had it plague me in influential areas like my career and relationships, as well as everyday areas like eating and sleeping. This past weekend, I regretted the feeling of not eating a 2nd Big Mac, but it was the right decision (right? Right?!!).

There are a few strategies I’ve found that are especially influential here. The first is to really dive deep into why I’m feeling regret, what it stems from, and eliminate (if possible) any notion that the decision was the wrong one. This includes both journalling and talking to people I trust about a decision and all the feelings that accompany it.

The second is to think of the opposite emotion, and when I’ll be able to experience it again. For the Big Mac, there will be a day in the coming weeks (or less) where I exercise a significant amount and feel good about eating it. For careers, there will be another role that I’ll feel as passionately about, especially if it’s my own project.

The last strategy on my list to dealing with regret is to, well, feel it. Some days it’ll drain me to the point of not being able to function, constantly thinking about those emotions. There’s no point fighting this, or suppressing it via other mediums. In fact, distracting myself only makes it worst, as it just delays the (eventual) feeling that I’ll have. So the solution is to feel regret of outcome; watch TV, listen to sad Drake, eat some Cheetos and go to bed.


I read a significant amount about ‘hacking’ life — daily habits, stoicism, frameworks to implement, etc. At the end of the day, I’m still human, and there’s something reassuring in that. I’ll feel regret, just as everyone else does.

The key is to discern between ‘regret of decision’ and ‘regret of outcome’, have a concept of the future, while still being present when those emotions hit me. Is it harder than it sounds? Of course! But knowing it’s the logical way to deal with things is enough for me.