Hello, Goals #4: Learning From Failure

Do you remember your most epic failure of all time? I do. I think it was the time I realized that I was throwing more and more money into something that just wasn’t working, but was too afraid to give up. So, I kept going until I really couldn’t anymore, dashing the dreams I proclaimed would come true and disappointing many in the process. I remember this distinctly because I was fragile enough that when I lay on the floor to take a creative version of a nap, my mom came into my backroom studio and thought I had actually fainted from working too hard and too long. I’ll never forget how worried she sounded. So I stopped and never napped on the floor ever again.

Or maybe it was the more cringe-inducing, embarrassing failure of the time I was called “unprofessional” publicly on Facebook by a group of university students, because I was trying to build up a career in photography and I had no idea how to herd 25+ people. Or how about the time, early in my career but with what I thought was highly relevant experience, I applied for a job 3 times total, each a year apart, at a company that I loved at the time, only to be told not to apply again. Or perhaps it was the time I was rejected from a fast-track computer science degree program because my fashion design degree was unrecognized by the university, even though just a few years earlier, I had been offered multiple scholarships to that same university, dashing my hopes to go back to school. If you haven’t gotten the picture by now, I really could go on and on, and this is just touching the surface of my many professional failures.

Airing my dirty laundry feels cathartic, to realize that they now seem so long gone and the dots seemed to have connected anyway, and I’m nowhere near done. But all the things I’ve mentioned above, they’re the “glamorous” picture of failure, the distinct moments that you can look back on and say, “oh well, I came out of that fine after all, so here’s my story”.

Here’s how I think of failure: they’re the different ways that pain, shame and other feelings we try to avoid, through time and effort and luck, shape you from what was once just a misshapen blob made up of thoughts, dreams and genes.

But when it comes to career goals, there is a slow-burning kind of failure, one that is so silent and deadly that most of us don’t even take it as failure: we call it procrastination or we avoid thinking about it at all, because hey, if we don’t succeed at something we’re the boss of and only we are impacted by, can’t we just forget and ignore? Who’s counting? Who’s looking?

We need to talk about failure: the non-glamourous, non-epic kind too. Because there’s nothing more insidious when it comes to getting what you really want than the overarching failure of not having a proper feedback loop for yourself, and never giving yourself even the opportunity to learn from what you’ve done and what you haven’t (and really confronting the why, even on the small things). And what happens when you don’t? Well, you fail again — different circumstances, same reasons.

Get SMARTER: Conducting your own retros

Did you know that there’s a thing called SMARTER goals? It’s SMART, but extra. But it makes sense and this is the last piece that I think the majority of people miss. E stands for Evaluated, and R stands for Reviewed. That’s a bit more granular than I prefer (but flows better than SMARTE or SMARTR, right?).

I think this is the piece most people, no matter how great they are at planning, miss. And if you miss this, you’re denying yourself the opportunity to grow from your successes and failures in a deeper way. I learned to do this for myself by borrowing from the world of work. It can be as simple as two questions: “What went well?” and “What didn’t go as expected and why?” These are the same questions that we’d ask at the beginning of each week, to reflect on the previous week. They became more insightful and important than “here’s what I did”. It was a perfect opportunity, taking less than 10 minutes a day, to think about what happened and why, and to avoid the trap of continuously doing the wrong thing and not realizing it.

It’s more important that you get into this habit for yourself. If you’ve ever worked at a company, you are probably familiar with the concept of a performance review. So think of it like a self-driven version of that, because no one’s going to do it for your own goals and dreams.

Everyone works a bit differently, so you may find goal-setting more effective if you review and adjust on a weekly basis (like I try to do on Sundays). You may also find it most effective if you review and adjust at a longer interval than that. But don’t expect to write your goals down and never look at them again, outside of ticking the done box. Ask yourself these questions, look at the goals you set yourself, and find some way to evaluate your successes, failures and challenges on an ongoing basis.

Identify your blockers

One important thing to look out for, after you’ve been around for long enough, are patterns. Conducting your own retros of course makes it easier to see what those patterns are, but mostly if you think hard enough and far back enough, it’ll all start to make sense.

What are the things that have always put a thorn in your side whenever you tried to reach a goal? When you look at all the things you wanted to do and the things that didn’t end up happening, is there a common thread?

For some people, this may be external, but more often than not, it’s internal. Is the problem that you never have time? Did you not have time to do this one thing that’s been on your list for weeks or months? You’re going to want to find a better time management system or de-prioritize other things. Do you need to take some time off to reset? Do you need to hire someone? Do you need to watch less Netflix? Do you need to rework your workday so you have time and mental capacity for deep work? Or, consider that this thing might not actually be the thing you want to do. Guess what: you have the freedom to drop it!

Blockers that don’t change become excuses.

The art of the graceful fizzle-out

Have you procrastinated on something for so long that it just sort of fizzled out, with goals that once seemed on the horizon now a hazy far away road, one that you never grasp no matter how long or far you drive? This is the other kind of failure, perhaps even more common than trying and not quite getting it right. But it’s the one that tends to eat at us, accumulating like a slow-growing poison, the one that doesn’t ever feel like an actual failure. It just sort of…dies.

There are many reasons fizzle-outs happen. One is the aforementioned: it just wasn’t something you really wanted. The other is that the goal felt too big: usually setting smaller steps works. Sometimes it’s as simple and obvious as: your “get things done” muscle has been out of practice and you’re in a rut of inaction.

But be very critical of things that never, ever happen, the things that you always start but never finish or ship, things that always fizzle out. Be ruthless and honest about why.

One of the best things you can do for your mental wellbeing is to gracefully bow out of a commitment you’ve made to yourself. What are the things that are permanently on your to do list? Is it time to say goodbye or are you finally going to get it together?

The dark side of commitment

I used to beat myself up when, after a few years of repeating my same old patterns, I realized that I could ship things fine, but I could never commit to one grand idea. Why do I keep doing this to myself? Why am I so fickle? The weight finally lifted when I realized that all it took for me was a reframe of my goals; I learned to focus on the actions, not the deliverables. The deliverables were a nice, pretty container for the actions. It was enough for me that I shipped something; growing it beyond that wasn’t something that was particularly interesting to me, for most of my work. And when I learned to respect my values and my inclinations, I finally got it.

One of the most important lessons I’ve learned about getting what I want is being open to changing what it is I want. So many of us stay committed to our goals, to the ambitions of our past, our peers, our parents and our fears — only to reach them and realize that the rest of the world was moving forward while we had our headlights on, shining in one direction.

My parents were adamant that we take Chinese language lessons as kids, and one of the very few things I remember is a folk tale about a frog who lived in a well. He lived happily in his well, only to feel embarrassed later on when a turtle comes along, telling him about all the beautiful things in the big wide world beyond the narrow circle of sky the frog could see.

I think there’s a lot to be said about the power of commitment to insulate against Shiny Object Syndrome, but there’s definitely a dark side too when it makes us our own enemies of growth. Think of it this way: What are you committed to, that’s filling up space that you could commit to newer, truer ambitions?

Now, Your Turn

That was a lot, wasn’t it? Let’s recap career goals for creatives in 100 words or less: There’s not one right way to set and achieve goals, but there’s a lot we can learn from codified systems. More importantly, there’s a lot we can learn from ourselves. Start macro (why and what), then get short-term and granular (how), use your creativity to find what works best for you, don’t forget input goals, evaluate and reflect consistently, and be open to change.

One last thing: I realize the irony and hypocrisy of it all, of everything I’ve said and everything that can be said about setting goals. In the end, it’s all a bit wishy-washy. Stay committed to your goals, but let go of commitments. Did you notice that?

This is why some people get it and some people don’t, why some people make it and continue to make it, even when they fail, or why some people never make it, even when they win. If there was a truly proven, one-size-fits-all system, we’d be robots or something close to it anyway.

But there’s a sort of fun that comes from knowing that there’s no one path, not one way. It’s all about knowing who you are, listening hard for what you want and what motivates you, and adapting continuously. It’s not about letting someone else, anyone else, even an article from a company you respect, tell you what you need to do. It’s about taking all of this and really learning how to manage yourself. You can get that job, you can make a career switch, you can make more money, you can get that gig, you can work on your dream project. You can change your life, if you learn to do that. Open your mind, keep your eyes open, stay true to your internal compass, and go for it.