Hello, Goals #1: Setting and Planning Career Goals

Back to school is one of my favourite times of the year. Just like New Year’s, and my conveniently-timed springtime birthday between the two, it’s another arbitrary calendar call to dream and scheme. I’ll take it!

I’ve been through many goal-setting systems and approaches from having none at all (except the mentality to hustle), to using calendar time-blocking, to a granular and colour-coded spreadsheet — there have been times where I’ve lived in procrastination land for months. During the second half of my tenure leading a team of smart and driven folks, I’ve come to gain a more intimate understanding of how goals shape our careers and our lives, even when we don’t reach them — especially when we don’t reach them. A long time ago, it seemed like I could never reach my long term goals because the world changed too quickly for me to accurately predict what I really wanted, all the while handing me what felt like random opportunities.

How fitting that, in a perfect circumstantial early fall storm, the first thing that I’m writing here starts at the very beginning: understanding who you are, what you want, and making a plan to get there. And don’t worry if the very mention of a “plan” makes you panic or eyes glaze over. There is a way to get what you want and set goals, even if you can’t decide what you’re having for dinner tonight. And of course, there’s plenty here for you if checklists are 100% your thing.

So read on to explore career goal-setting for creatives, the SuperHi way. And follow along by downloading our free PDF worksheet to work through planning goals.

Hello, Goals: A Philosophy on Goal-Setting

Why we need goals

One of the first things I started to realize after my colleague and SuperHi designer Kristen (and creator of our companion PDF worksheet) put out a team survey to gauge how people thought about career goals is that we all, even on a team of high achievers, have our baggage around goals. We say things like “well, I don’t really set goals per say”, “I’m not a very goal-oriented person” or “personally I don’t do career goal setting” (all true words said by some smart people who’ve done some really cool things), underlining our narrow perception of how goals work. Well, if these people don’t set goals, what hope is there for the rest of us?

I started to think about this, and the rest of this guide stemmed out of this initial brainstorm.

Goal-setting isn’t one-size-fits-all, and doing the whole SMART thing increases the likelihood, scientifically, of achieving goals, sure.

A goal, the only true definition of one, is “the object of a person’s ambition or effort; an aim or desired result.” It is not related to a one specific way of thinking, a methodology or system. Certain people aren’t more “goal”-oriented than others. We are all the product of our own ambition and effort, however we approach it. What works for you may not be a nameable system at all! It’s whatever. You. Want.

But, I don’t think you can commit to career goals prior to knowing what you want in life. There’s the why, and then there’s the what. Going for the what first is a surefire way to lose sight of why you’re doing anything at all.

So that’s where we need to start. Not by sorting through a mess of goals and dreams your parents, peers, societal norms had for you and getting all SMART about them. It’s understanding who you really are, assessing your history of achievement or lack thereof to see what worked and what didn’t (this is why I think that getting good at reaching goals gets easier the older you get; you have more historical data — unfortunately, this also coincides with a strange societal expectation that we stop growing and learning after age x).

Another of my colleagues, Jake, put it in a way that was simple and that I and many will identify with: goal-setting isn’t necessarily about the end goal, but about achieving a sense of momentum, a direction of forwardness. We are always moving, even if we don’t think we are. In what direction? Forward, backward, upside down, in circles? It’s up to you to decide where you want to go. And that’s why we need goals.

SMART, the modern way

SMART stands for Specific, Measurable, Achievable, Realistic, Timely, and has become the gold standard for goal-setting (shoutout to SuperHi COO Adam’s corporate days and anyone else who’s googled ”how to reach goals”). But sometimes, methodologies have a way of feeling restrictive. You look at the system and as you’re reading through each line item, it all makes sense but it kind of also feels like too much. And then you wonder if the stories of all the people you admire were SMART success stories — is leaning into this methodology really the key? You read through biographies or listen to podcasts or think about your high school reunion and all the people who’ve made it and hmm, it sounds like most people get lucky and/or work hard and that’s it. You don’t really remember anyone mentioning SMART at all, so is it all just a big self-help ruse?

What we don’t realize is that systems are the undercurrent of any kind of success, biological, economic, personal — just like systems that make the world go ‘round, they’re invisible heroes. Documenting them and breaking them apart just makes the invisible currents more accessible. The key here is to think of SMART as a theory for why goals work, and to adapt the how to your own proclivities.

I’ve failed and fizzled out enough times to realize that I’ve gotten it wrong. But I’ve also succeeded enough to know that I’ve gotten some things right.

So instead of breaking it all down and telling you that you need to write goals that are SMART and leaving it at that, rehashing what you may have already heard and applied to some success, I encourage you to think about how you set goals now, and what the missing piece of the puzzle is. For example, you might be great at identifying goals but perhaps you’ve always left out the “timely” piece of things. Then you know you need to work on that, because the rest comes naturally. You don’t need to change how you’re already working in order to achieve your goals. All you need is to do you, but better. Take stock of what you’re already doing well (what happened all those times you did achieve a goal?) and it’ll become clearer what was missing when you didn’t get there. Use the rest of this guide and worksheet to break things apart, understand why and how, and orient towards what you want.

And if you’re not sure what even you want, well let’s start there, shall we?