Set Worthy Goals

[This is the first in a series of posts on setting, executing, and accomplishing personal goals. This first post is on the strategy of goal setting, the next will focus on executing. There’s also another upcoming post on OKRs and effectively and efficiently accomplishing company and organizational goals distinct to this.]

We all set goals. Few reading this lack aspiration. But graveyards full of New Year’s Resolutions show there’s a deep disconnect between people setting and accomplishing goals.

So, how do you set goals that are actually going to move you forward and then get them done? Particularly, how do you work on the long arc goals that are the really satisfying ones that are accomplished over years? How do you even scan for a future in which you’ll very likely be a different person than the one you are now? And how do you And also, avoid the productivity-pr0n and hustle-culture that just keeps you busy all the time but effectively running in place?

1. What Makes a Goal Worthy?
2. How Do I Set Them? (often amongst too many choices)
3. How Do I Then Execute and Achieve them? (covered in another post)

What Makes a Goal Worthy?

This is not a “5 easy steps to” post. The most worthy and satisfying goals require effort. And time to achieve. They stretch you in attaining them. Worthy goals make you into a slightly different person than the person you were when you set them. They require persistence and their achievement involves struggle, practice, and time.

And while everyone’s definition of worthy is somewhat subjective, I find that truly worthy goals fall into five categories:

1. Growth
2. Identity
3. Creating
4. For Others
5. Relationships

(Probably an important side note here: there’s a difference between a goal and a hobby. People confuse goals with how they sometimes decide to spend their time. Do not. A hobby is something you practice regardless of your level of skill or progress merely for your enjoyment of it. You have permission to be bad – forever. There is literally no goal. You’re simply doing the thing. You can attempt to get better at it, but that can erode the permission it gives you to do something that does not require you to excel. So, make sure you have room for those and distinguish them from goals. As an example, you may love cooking, perhaps to make friends or family happy, it doesn’t matter. It also doesn’t mean you have to Masterchef everything or try to figure out how to monetize it. That’s a possible way to ruin something you love.)

Growth

What’s a Growth goal? Growth is about goals that enlarge you. Primarily growth goals involve:

1. New skills - capabilities, competencies, capabilities, or loves to add to your life
2. Mastery - Taking existing skills to new levels

Achievement isn’t the milestone you reach, but what it unlocks: new and greater challenges for your life.

Growth goals expand the potential frontier of things you can do with your life and open up new opportunities.

Identity

Worthy goals tie to identity change.

These are about evolution. On who we want to become (in fact, as a general rule I recommend setting goals about who you want to be rather than what you what to accomplish). I straight up lifted this idea from James Clear, but I think it bears repeating since it’s a powerful one. Successful goals are often set with the idea of changing who you are. So, rather than achieve a fairly empty one-off goal, create a system of habits that changes you into this new person.

• So, don’t just hit that 10k. Become a runner.
• Don’t just write a newsletter once a month. Be a writer.
• Don’t focus on the degree. Transform into a scientist.
• Don’t just take that whirlwind trip of Europe. Evolve into a traveller.

The difference here is most people set milestone goals as catalyst, or even proxy for what they actually want: to get in shape, to do more interesting work, to find a partner, to add to their life. But quite often, even if they achieve that 10k it does not extend into the change in who they want to be.

So, be clear about who you want to be at the start. Sure, you can hit that 10k but there should be another milestone right after it (for example, I often have it as a personal rule to always have a trip pencilled in on any one I am coming back from. I kinda like to think that it helps make me more a traveller than tourist.).

Creating

The act of creation, of adding something positive to the substance to the world, is almost always worthy.

It can take any number of forms: art, ideas, invention, causes, to founding things. The act of creation is arguably the most impactful and enduring of goals. For something created can’t really be taken back.

They are also the hardest, since they carry the risk of criticism and possible rejection. So, the risk versus reward thing is here. For some people, they’re simply wired to create and can’t help themselves, but for others this is a conscious act of setting these goals and habits, doing the hard yards, and putting something out into the world.

I am also using creation quite broadly here and in a positive sense even though there is value in both destroying and maintaining things.

Removing an unjust law and creating better, fairer ones is, essentially an act of (re-)creation, but impactful beyond the personal.

So too, maintaining things also has merit and effectively we all owe a debt reading this to the many open source maintainers across the internet who altruistically keep the software and gizmos humming that keep the whole thing spinning. Few people get credit for maintenance, since there is such a bias to creating new, but it’s something we should celebrate as both worthwhile and admirable.

For Others

Goals in the service of others are amongst the most satisfying. Perhaps because, as I mention in The 3 Pillars of Happiness , we are social animals and contributing gives us a sense of meaning and belonging, but I have to say that of my goals that make me feel the best and happiest, many are around the charity work I do. Often much of this work is not even using my advanced skills (though I worked professionally in NGOs for several years), but basic contributions such as showing up, doing the low level work, and volunteering for things, causes, and people you care about have clear correlations with both a sense of achievement and well-being.

I actually highly recommend everyone should volunteer and contribute in some way that isn’t just a side hustle for themselves or CV building. Find something and wade in. Most organizations will always have something for you to do if you can put pride aside and do the less glamourous, but necessary, work that really needs doing.

Relationships

Finally, goals enhancing, adding, and deepening meaningful relationships rarely misfire.

They add a deep sense of belonging and quality to your life satisfaction. I have certainly never regretted them. Basically, spend time with people you care about and can help. Give them what you can to nurture and grow them.

And go beyond just the individual focus on family and friends. Find your tribes. Do stuff with them that feels like it matters. Do a trek, climb a mountain, visit someplace you’ve both never been before together (or do something you’ve never done before in a place you all know well).

An additional side benefit here that research and scientific literature support, is that goals deepening relationships are highly correlated with happiness, a sense of well-being, and perceptions of life satisfaction.

Things to Avoid

Acquisitive Goals

Acquisitive goals rarely provide longer term satisfaction or happiness. And even more rarely a sense they were worthy.

There are entire reams of research written on the short-term hedonic treadmill effects of having acquisitive goals. They give you a short-term bump but are ultimately unfulfilling and need another acquisition “hit” in order to give you a bump again after the initial feeling wears off.

So, try to avoid acquisitive goals surrounding money, objects, or accolades. As a general rule, if it can be bought directly, it’s rarely something that’s going to make you feel accomplished in the long run (doubly so in this age of planned obsolescence.).

At least for me (and recognizing YMMV), I find acquisitive goals I have had in the past are usually masking the actual goal I am trying to accomplish — or are bad proxies for things that should actually be goals. In some cases, the distraction they’ve caused or costs they’ve imposed on me (the things you own, really do end up owning you. Tyler Durdan was right.) has even prevented me accomplishing or executing with proper priority larger goals I should be pursuing. So, acquire wisely.

Acquisitive goals end up being window dressing to your life, not your actual life. And people often confuse the way they look with leading a good life. Avoid this trap.

If you feel the need for an acquisitive goal (like a house, car, money, degrees) get down to the core reason you actually believe you need those things. Doing a five whys diagnostic exercise is actually helpful here.

An example: home ownership. Owning a home in order to create a great environment for raising a family is a worthwhile goal , or even for avoiding the justifiable angst around housing insecurity. Buying a house simply because of adulting pressure, as an investment vehicle (it’s generally a poor one compared to other options), status, or as a societal default, is perhaps one you should reconsider carefully. Know what your real goal is in order to actually accomplish it.

Goals for Goals’ Sake

A trend I’ve really noticed even before covid is an overloading of goals. Hustle culture and always having the need to appear productive, and having way too many goals going on rather than focusing on a few key things you want to do. Sure, it’s ok to have secondary goals, but setting clear, unambiguous priorities and then making sure your calendar time aligns with those things is amongst the best ways to make sure you get done the things you set out to do.

So, be careful of spreading yourself too thing or spending time on too many goals when you should know the ones you ought to be spending time on.

Too many goals turns everything into aspirations, detracts from making actual progress on things that matter, and suffers from the “peanut butter problem” — you spread so little of yourself over too much toast that you can’t taste anything.

I really recommend for anyone with a busy life, to manage “work in progress” for anything which doesn’t require actual effort and maintenance time.

For me, and I imagine other busy people reading this with work, life commits, friends, and kids, that probably means only working towards developing 3 goals or habits max at a time.

Some of these you can game by turning them into habits, after which, they require less effort and to progress, but inculcating habits and having them stick is hard. Particularly if you have a life where having a consistent routine is difficult (ie. so most other peoples’ lives but professional “content creators”.). So, WIP is your friend.

How Do You Set A Worthy Goal?

Figuring out what is actually important to you is hard.

In a world that is bombarding you continually through advertising what you should be wanting every day, it’s hard to hear yourself. Culture too and social pressures and proofs can also end up having an insidious effect on goal selection. And you don’t want your true goals being slight variations on keeping up with the Joneses. Even trends that seem to buck this like minimalism, mindfulness, and spirituality seem, at times, to have been corrupted into just other mechanisms of consumption and elitism rather than truly nourishing.

So, introspection is required.

It doesn’t have to necessarily be hard. There’s no need for a retreat, drum circle, or similar isolationism (though a theme trip is always nice.). But it does require some quiet thinking time.

What’s worked for me is spending a weekend day in a quiet, bright coffee shop with a notebook or pad and really thinking about the things that are really important to you. What sort of life do you want to be really living? Who do you want to be? What are the key pillars to support those things? And what trade offs are you willing to make for that?

There are a bunch of different tools, especially for longer range goals, that might be useful to reflect on here, like the (excellent) Designing Your Life out of the Stanford D School, as well as the idea of 5 year Odyssey Planning, but sometimes if you just spend some quiet time in a comfy place, with a clear mandate on a list of 3-5 goals for the next 12-18 months, you can do wonders.

If I had one piece of advice (which seems to be backed up by science) it would be: Decide who you want to be. Think about your identity rather than merely what you may milestone or want to accomplish. Ignore the naysayers.

Big Rock Goals

We’ll cover this off in another post, but I have a bunch of Big Rock goals I use to steer my life towards.

These are five, broad, “shape of my life” goals and guidelines to help me make larger decisions about direction and longer term interests. I’ve found I ignore them at my peril when I don’t refer to them on larger life decisions. Or worse, let doubt and self-conciousness override them and make bad choices in spite of them.

These are goals that speak to the type of life I want to lead and to have. I imagine mine would not work for everyone, though I’ve spent a bit of time thinking about them and they seem to tend to align along axes that have support by happiness and well-being research (before I even knew a lot about those). And so far, I’ve seen little reason to change them over time (though sometimes I feel with choices I make sometimes, even a recent one, I’m feel I’m far from them at times.)

I put them here simply for reference, and just because I realize the section is way too abstract and fluffy without them. I really do believe having these (when I listen to them) has helped make my life better and helped move things to that state that my life is in today. Take them as inspiration and figure out what yours should be.

How do they work? Every year, I assess where I am regarding these and try to make changes to where I am and what I am doing to nudge my life just a little bit closer towards these ideals. A little harder, especially after I’ve made a bad life decision, is at least moving my life away from the things that are clearly moving me in the opposite direction to these goals.

(Why Big Rocks? The idea comes from, or the tale is at least popularized by Stephen Covey’s seminal book The 7 Habits of Highly Effective People. Fill your jar full of the big rocks first else you won’t be able to fit them in versus the pebbles and sand that prevent them from being fit in. At least, that’s what I’m supposed to be doing with them.)

Annual Goal Planning

Every year, usually in the “dead time” between Christmas and New Year’s, I sit down and think about the bigger buckets of things I want to accomplish in the next year. Also, I take a long, hard look at my life versus the Big Rocks. And set some priorities for the year ahead.

Sometimes these goals change as the year evolves, or I learn more, but in reality, they tend to stick for the full year and act as guardrails. If at the half year, your progress on them is terrible, you need to make a hard right and make some changes in your life.

<rant>
Be very wary of confusing your job with your goals. Sure, if you feel your work is your life you can do that, but at least in my experience, my jobs are the things that actually knock me off-course from my larger life goals.

Yes, everyone needs to make money and you may not always have choices (and why I’m a strong advocate for making financial independence from job employment a life goal and living within your means, so you can make good choices about job demands rather than being held hostage by them.). Red flags like overuse of the term “loyalty”, overwork quoting high performing teams, or other extreme commitments not in line with the value to compensation of your labour are usually indications of a toxic work culture or badly run companies. Be wary of companies that are not supportive of your larger life goals and aspirations.

Sadly, bad companies are willing to treat you like a tube of toothpaste to be squeezed till you’re expended, then tossed. Decent companies provide training budgets, make sure you’re taking time off to rest, and have non-dysfunctional HR departments. Great companies try to support you in your life goals and try to help mentor and guide your larger career even outside of your time with the company.

Try to work for only the decent to great if you can, even at a lower salary, and even if you’re not working towards independence from job-based employment.

Better yet, if you are someone who is in a position of being able to influence or execute this in your company, strive for great. Contribute to it. You can actually implement a simple, low-lift career progression framework which (I can tell you from personal experience) will make a huge difference both to your company in terms of attracting talent, retaining them, and growing leaders, as well as the people who work for you.
</rant>

Rant aside, the review on my Big Rocks annually usually (ok, always) yields at least a pair of goals and habits that I want to incubate during the year.

How Do You Find Your Goals?

I’ve always been in slight awe (and, suspicion) of those people, when I was in undergrad, who showed up to Uni knowing precisely what they wanted to do in life. I’m not sure how many of those people ended up happy in their declared end states, but for the rest of us, we are forever works in progress and perhaps need a bit more help on goal setting.

So, if you’ve gone through the list of worthy goals above and find yourself lacking inspiration or ideas, how do you come up with some good goals? How do you live a life less ordinary?

I suspect most people simply have no reliable way of introducing new “stuff” into their lives. We often travel the same paths every day, wearing a deeper groove in the path of our lives that makes introducing or trying anything (truly) new in life, difficult. In this mode, I find many people merely add goals that are really variations on a theme of what they’re already doing (which I’d say is distinct from “mastery”.).

I think one things that has worked well for me is trying to systematize introducing new things into my life. Here’s what I do. YMMV.

Experiments

One technique I’ve found has worked really well for me is Experiments. 3-4 things a year I want to try for the first time.

I’m often surprised at the things I’ve added to my life that have given me immense joy and grown me. Not all of them have led to goals (and some have been outright fails), but they’ve enlarged my life in both the ideas I am willing to entertain from lifestyle design (from sabbaticals, to PhDs, to career changes, to new places I’ve lived) to I’ve added to my life which have added substance, richness, and joy to it. So, even if you’re sceptical of this approach I suggest you, uh… experiment with Experiments. =]

Yes, you could reduce this entire section down to “Schedule trying new things. Be methodical.” if you wanted to, but stick with me.

Simply try to do 3 new new things you’ve never tried before over the next 12 months. That’s it. Come up with a top 3 lists of things that are going to be absorbing enough that you’d need 3-4 months to get them going and figure out if you like them or not. You have total permission to write them off after a decent amount of time (and relizing that everything new, in the beginning, feels uncomfortable.).

Make them small enough to not mess up, but big enough that you could keep them going if you really wanted to.

I find skills-based experiments work better to start since there is clear and unambiguous progress (or not) you can point to, and generally these are things you can buddy up for (or hire someone) to keep you consistent and accountable (like a guitar teacher, trainer, or tutor).

For example: This year I decided I wanted to

1. Learn Italian (ahead of a holiday I wanted to take and with pondering Padua for my PhD)
2. Learn pottery making (so I can make all my own crockery moving into a house again)
3. Workout switchups (to hopefully hit fitness goals around consistency and health outcomes)
4. Do Emergency Medical Responder training (mostly so I have an actual skill when the zombie apocalypse arrives)

Figure out your list. You have permission to be whimsical or random. For example, one goal I put to the side because of the friction of trying to do it as a digiatl nomad in the location I was living was my pilot’s license. One year, I learned Bollywood dancing with a partner for a friend’s epic wedding I was invited to. Start small if you can and figure out if you really like the thing. The more outside your comfort zone or regular trajectories a thing is, the better.

Make Your Luck

Another thing, which may be a bit counterintuitive is to open yourself up for more luck.

What do I mean by that?

Again on the above problem of people’s lives running on rails: They do the precise same things every day and almost every weekend, punctuated perhaps by a new restaurant or such. The French have a saying for it “metro, boulot, dodo”. You commute to work, you stay in the office, you go back home and sleep. (I think “netflix-ot” should perhaps also be added in there. I find most people who complain to me they don’t have time to do the type of things I do are usually spending 3 hours a night with netflix or doomscrolling Insta.).

Doing something as simple as walking home via another route or deciding to switch up your routine open up new opportunities if you keep your mind open to them.

Need some other ideas? I wrote an [entire post on How to get Lucky . Short version: It’s an attitude and a practice any way of being, not a supernatural force.

Even in a busy life there are opportunities to switch things up to make your life more open. And openness, at least in my experience, leads to you being luckier through exposure to a greater range of choices and opportunities.

Say yes to that dinner with the friend you haven’t seen in a while. Stop in for a trial lesson at the BJJ school. Flip through the course extension catalogue from the Uni, or search on something you want to learn on Coursera.

The expression about having your “hook always set”? It’s that. Have an attitude of openness to experience and possibility and following the path of things that intrigue you. Try something that has piqued your interest and at least find out if it has legs.

I also find having a “Hmmmm…” file helps. Something to keep a list of things to investigate when you have some down time or such, but overall

Fin

Since this post is specifically about choosing worthy goals I’m cutting it here before it drifts into areas around making them achievable, executing, and course correction.

If not obvious from the above: you need to write your goals down.

Making things explicit is one of your most powerful tools in terms of not just being clear about what you want to do, but also allowing you to tell if you’re trying to do too much.

After that, it’s pretty much just a matter of set up and starting. There’s a scary power to just starting even if you’re not really ready.

And after that it’s just reps. 90% of your results will come from just repeatedly working towards a thing, not giving up, and just getting back at it after setbacks (especially after setbacks). So, ignore the naysayers and just keep showing up.

So, that’s it. Sit yourself down, write down a few things you can commit to, and get going. It’s not easy, but nothing worthwhile ever doing is.

I hope you found something interesting and useful in the above. If you read the above and think there is something else I should know about, try, or include, please feel free to ping me. I’m always looking for better ways to get what I want to get done done. And always curious to hear more about what’s worked well for people.

If this post was useful to you, please lemme know via mail or elephant below. Feel free to mention or ping me on @awws on mastodon or email me at hola@wakatara.com .