When F*cking Up Is the Best Way to Learn

March 3, 2018

Here’s the thing about other people’s advice: It came from their experiences.

That’s what often makes it very good advice we should aim to follow. It’s also what makes it so difficult to take in and internalize — it came from someone else’s experience.

There are some things that just don’t seem to sink in until you’ve experienced them for yourself.

Why Everyone in Boston Is Going Crazy Over Houses

I feel like that’s the only way to explain what’s currently happening to otherwise smart, thoughtful, reasonable people in Boston right now.

The housing market here is insane. Absolutely nuts. Not only are prices soaring ever higher, but the competition for what’s on the market is intense.

Many single-family homes are selling for more than $100,000 over the asking price. Bidding wars are inevitable… if a seller even looks at your offer, that is, which probably looks sad and unappealing next to the offer made by another buyer who can pay all-cash.

Still, lots of people we know are looking to buy their first house. They’re stressing their financial situations to the max — and in some cases, beyond the limits — just for the privilege of accepting a whole lot of debt and saddling themselves with the responsibility of home maintenance and repairs.

We thought about joining these herds of anxiously hopeful homeowners. After all, we thought, we wouldn’t buy a single-family home. We’d buy a multi-family home, live in one unit, and rent out the rest so someone else paid the mortgage.

It was a good thought. But the more research we did on the financial aspects of owning a home — even an investment property — and the more we faced the reality of the current real estate market in our area, the more disinterested we became.

The finances didn’t make sense and didn’t fit into our overall financial plan, so we dropped the idea.

Without Your Own Experience, It’s Easy to Let Emotion Take Over

People may associate a stigma with renting — or they may hold tight to an idealized version of what it means to own a home. Either way, both are based on emotion and feelings, not facts and logic.

If you can take the emotion out of it and consider the homebuying from an objective standpoint, it’s clear that most people currently buying would be financially better off renting.

That’s what we realized for ourselves, and have been happily hanging out in our rented condo in the South End — where the landlord hasn’t raised the rent in three years! — ever since.

I don’t think I’d have been able to do this had I not already gone through the process of buying and selling houses in the past. I held no romantic ideals about home ownership, so it was easy to just focus on the financial side of things and make a rational, logical decision.

Had I not learned from past experience though, would have have been so easy to do? I’m not sure.

A house is work. It’s a huge responsibility. It’s expensive. I know this because I already went through it.

Those experiences allowed me to see the great things about home ownership and the downright crummy stuff that quickly popped any fluffy, rose-colored notions I might have had about what it meant to own my own place.

Which made it way easier this time around. I can confidently say that right now, owning a home does not provide me with more value than I get from renting my current apartment. 

Buying a house is far from just a financial decision for most people. It’s an emotional one, and I think that’s why many people struggle to disengage from the idea of home ownership even when it’s objectively a bad financial choice.

None of this means I won’t ever buy a house again. I hope to in the future. It just doesn’t make since right now.

But I needed the experience of going through the whole homebuying thing to actually get that. Everything I “learned” through that experience was stuff I already knew on an intellectual level. I didn’t discover anything I hadn’t heard or read about before.

The difference was, instead of learning about it, I was living it.

Experiential Learning Is a Different Way to Gain Knowledge

Experiential learning is the process of living through your lessons learned, rather than having someone or something instruct you in that lesson.

And sometimes you need experiential learning to really, deeply understand something.

What you need to experience for yourself before you “get it” varies from person to person. Not everyone needs to experience the same lessons.

For me, I had to screw up a lot of important things in life to go through the process of learning who I was, what I valued, and how I wanted to live my life. All the advice in the world wouldn’t have saved me from these mistakes. Living them, and facing the consequences, and figuring out how to pick myself back up was the only way I was going to learn with some stuff.

What I talked about above, with buying houses, it’s just one example. The point is, we all have something like this in our lives. Something we need to experience and not just be told, or hear about, or read through.

It’s a different and powerful way to learn and expand your knowledge. Of course, it also leaves you vulnerable in a way that “book learning” doesn’t.

Pursuing experiential learning opportunities means opening yourself to the reality that you’re gonna f*ck up from time to time.

How to F*ck Up Without Totally Ruining Everything

That can be scary, especially if you’re a perfectionist like me. I hate getting things wrong, or screwing them up, or not doing as well as I think I could have.

Experiential learning is tough for me to embrace for that reason. But mistakes and failure and f*ckups are incredibly valuable if you take the time to reflect, analyze, and process them.

They can also derail a whole lot if you’re not careful.

This isn’t carte blanche to go out into the world and intentionally f*ck things up. I would certainly encourage anyone to learn as much as they can from the wisdom and experience of others so you don’t need to go out and repeat past mistakes — yours or someone else’s — only to verify, yup, still a mistake.

Try to stay open to advice from other people with similar values to yours and who have been in similar situations to the once you’re facing now. (Don’t worry too much about what other people tell you if they have completely different values.)

Read and do your own research, too. Seek out ways of informational learning, whether someone teaches you or you teach yourself.

But know that there’s a time and a place for experiential learning that could provide you with amazing insight into how you want to live you life. Also know that those experiences might not go perfectly smoothly at all times.

Give yourself room to mess things up. You can do that by:

  • Having an emergency fund and cash savings
  • Getting the right insurance policies
  • Eliminating existing debt
  • Cultivating supportive community or network to lean on
  • Setting up a strong financial plan that can withstand some bumps and bruises along the way
  • Maintaining good relationship with yourself so you can avoid wasting time judging that self for your mistakes

…and so on.

When it comes to giving yourself space to make a mistake, you need two kinds of space: mental and practical (or financial).

Mental space means accepting f*ckups and forgiving yourself when they occur. Practical space means having your financial ducks in a row so a failure in one spot doesn’t mean all is ruined.

When you do take a misstep, acknowledge it. Forgive yourself for your mistake if you need to; don’t hang onto it and continuously beat yourself up for messing up.

Finally, reflect and evaluate. What happened? What did you feel when you made those decisions? Why did you make that decision in the moment? What does this mean for the next time this situation occurs?

Take a serious and honest look at the experience and embrace what it can teach you. Doing so now can help you make more informed decisions about what’s right for you — even in an emotional moment — and prevent future f*ckups that you might regret.

If you’re digging what you’ve read so far, I’d love to invite you to join us — and maybe even try your hand at going beyond wealth, too.

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