An incomplete list of 30 things I learned in 30 years

30 lessons in 30 years

Words by Madeleine Dore

When we commence a new decade in our lives, on the one hand we can view it as meaningless – age is just a number, after all.

On the other hand, we can view a number as a marker. Uncertainty means that there is always a blank canvas in front of us, but like a new year, a new decade helps us put a frame around it. 

Recently speaking with a 90-year-old woman named Margaret, after recounting extraordinary parts of her life story, she was quick to assure me, “You can’t arrange life, it happens around you.”

As much as we want to arrange or plan our life year by year, decade by decade, we are shaped by what happens around us – the opportunities we seize, the people we encounter, the places we stay or leave.

Moving into my 30s, instead of viewing this decade as a chance to start anew, change or improve, I want to see it as a chance to truly take notice of what’s happened around me.

We might not be able to control events or the outcome of our efforts, but we can put ourselves in the world and take note of what we learn along the way.

Reflecting on the articles, interviews and experiments I’ve conducted in the last decade – and the first five years of my writing career – here’s what I’ve understood so far, perhaps only partially, as every lesson is one I often have to remember to learn.

1. Hold plans lightly

In a month of commencing my day with a commencement speech, I learned to pay attention to what’s on the periphery. Our plans for ourselves can lead us astray because we don’t really know if we want something until we try it – don’t be afraid to experiment with something, and change course if something’s not for you.

2. Taking action is more important than figuring out the right decision

Of course, it can be helpful to survey the options available to us. But it's when we get caught up in determining which is the "right" decision that we get stuck. Even with hindsight, it's impossible to trace our current lives back to one specific choice or opportunity. Focus on the process rather than the outcome of your decisions.

3. Don’t believe the parameters people make for you

In my early 20s, I was told on my multiple occasions it’s impossible to solely write about creative people, or that I’m not “cut out” for a career in the creative industry. Instead of taking their advice or so-called insights at face value, I tested the parameters. I went on to write hundreds of articles about the arts industry, and interviewed hundreds of creatives about their lives. Don’t let people tell you who you are or what you’re capable of.

4. Remember to question your own rules, too

While other people might try to tell you what you’re capable of – either directly or indirectly – the loudest voice when it comes to shutting down our plans is often our own. We make up rules for ourselves to follow, or create metrics of success that only get in our way. Reflect and reassess your own rules often and critically.

5. Notice when you’re caught up with the fantasy

When it comes to failure, be it of a relationship or a work opportunity, often what stings the most is the loss of a hoped for future, which can quickly become a lingering obsession or fantasy. Our head can say ‘it was for the best’ but our heart can keep us stuck in the past. Try not to miss what’s here for you now because you’re chasing a ghost – focus on what your current day contains to heal heartbreak.

6. When you can’t find the job you want, create it

When surveying the careers of people I’ve interviewed, from Zoe Foster Blake to Rachel Burke to Mari Andrew and Chaz Hutton, it’s side projects and personal work that has really shaped their careers. Don’t wait for someone to hand you an opportunity, make it for yourself.

7. You’re not ahead, you’re not behind – you’re your own measure

Throughout my early 20s, I couldn’t shake the feeling I was behind in life. I still have a habit of calculating how old someone must have been when they experienced this success or that, to figure out how I measure against them. I have to remind myself that how you measure your life is of your own making, and comparison is nothing more but the thief of joy.

8. The more you do what you want, the less likely you are to compare

The antidote to comparison is to do more of your own thing. In the words of Alain de Botton,"The more you know what you really want and where you are really going, the more what everybody else is doing starts to diminish."

Let comparison or envy be a guide for what you most want, and then create that for yourself in your own way.

9. Most things can be done in 45 minutes (you need less time than you think!)

As a chronic procrastinator, I’ll often find myself ashamed over how quickly something can be completed when I finally get around to it. Creating Side Project Sessions means that I finally have a regular space to do that thing I’ve been putting off, so I don’t have to carry the guilt of not doing it around. It’s also taught me to value the break as much as the work.

10. “You can be the ripest, juiciest peach in the world, and there's still going to be somebody who hates peaches.” – Dita Von Teese

I’ve spent a lot of time trying to mould how people think of me by overcompensating or apologising or making myself smaller or larger depending on what I assumed someone would prefer. It’s futile – you can’t control how people think of you, so you might as well show up as yourself.  

11.  What you do for a living doesn’t impress people as much as you’d think

People care less about what you do for a living and more about how you make them feel. I often get anxious being asked ‘what do you do’ because I thought what I do had to be interesting to others, but I’ve learned to treat it with lightness and playfulness because often times, people aren’t paying that much attention to it anyway.

12. There is a difference between consistency and intensity

Don’t think you have to be constantly producing to be consistent. As author of Start with Why Simon Sinek explains in a lecture, there is a distinct difference between consistency and intensity: “Intensity is like going to the dentist, it is fixed in time, we know exactly which date we are going, we know how long we are going to be there, and we know when we come out our teeth will feel smooth and look pearly. But if that is all we do, all our teeth will fall out. In other words, intensity is not enough.”

13.  See what you haven’t done yet as possibility, not failure

As a list person, I used to view everything I hadn’t done yet as looming failures – there was an inner dialogue that I was incomplete because my to do list was incomplete. This was overwhelming, but now I see how everything on my list is a possibility – it’s exciting to have ideas and things to look future to doing in the future, not daunting.

14. The best thing you can do with your privilege is acknowledge it, and not waste it.

Being able to pursue a career as a freelance writer and navigate the uncertainty that comes with it is a privilege – I don’t have dependants, I have savings, and I have an education and I have choices. Much of the challenges I am curious about including procrastination, making time for creative projects, getting over self-doubt, and finding rhythm and routine in creative work are challenges that stem from having the privilege to purse what you want to do in the first place. I’m aware of this privilege, and slowly learning to seize the fortunate access I have to explore my curiosities, rather than diminishing them or taking them for granted. Graciously use the opportunity you have and bring people up with you.

15.  Opportunities flow through people

In my year of meeting strangers, it was a surprise to see that most lucrative writing jobs and opportunities have flowed through a stranger I met in this experiment. I wouldn’t say it’s entirely who you know that brings opportunities – but it’s certainly a large part.

As entrepreneur Ben Casnocha told said to Jocelyn K Glei in an interview: “Every opportunity is attached to a person. Opportunities do not float like clouds in the sky. They’re attached to people. If you’re looking for an opportunity — including one that has a financial payoff — you’re really looking for a person.”

16.  There will be ebbs and flows in your career (and days!) and you have to see the beauty in a plateau

There will be times you are winning and times you’re losing, and it can be helpful to start to notice your own nature ebb and flow in your creative practice.

As Debbie Millman put it, “Sometimes my personal creativity is just barren and sometimes it's really fertile. Right now, I'm in a very bountiful time, writing and a lot of illustration work, which I'm really excited about."

17.  Nobody knows what they’re doing

This project has allowed me to see behind the highlight reel and realise that nobody knows what they are doing. Everyone has sleepless nights, dull days, creative lulls, abandons projects, experiences rejection, and battles with self-doubt. When we keep in mind that no one knows what they are doing, instead of feeling like it’s impossible to catch up, an opportunity to learn how others move through uncertainty in their careers opens up. 

18.  Get rid of ‘should’

We can be bombarded by so many shoulds – whether observed or generated internally – that can leave us overwhelmed, stuck, or not really doing what we want to.

As musician Lisa Mitchell put it, “Everyone’s got this idea of what should be happening, or how they should be doing it. At the end of the day, success comes and goes, but if you’re still doing something – even if it’s hard – you’re meant to be doing it.”

19.  Movement and creativity are linked

When I’m stuck, it’s often because I’m looking at everyone’s else’s life through a tiny screen on my phone, have been in my own head for days, or have been sitting at my computer too long. When I get outside and move my body, I see how much more possibility there is and how much wider the world, and therefore my perspective, can be.

Shifting the focus of movement and exercise to being key to my creativity, rather than the appearance of my body, has also been a key learning in my 20s.

20.  Protect your solitude and alone time

We mistake being alone with doing nothing, or we steer clear of it because we confuse it with loneliness. We allow our work, social and family schedules to zap our time alone. Endless opportunities for distractions mean that when we are alone, we are not truly alone – we have the world at out fingertips, and opportunities to compare ourselves and our work with each scroll we take through our social media newsfeeds. To protect my own sense of my self, my connection to my writing, and my confidence, I need to protect my alone time.

21.  Triggers and checkboxes are more realistic than the perfect routine

Sustaining a perfect routine isn’t really conducive to being human in a world filled with distractions and unanticipated happenings. Having small daily checkboxes rather than a rigid routine is more doable.

As Austin Kleon says, “I think routine is so important, especially when you're getting started creatively, but for me right now, I almost need checkboxes and rituals more than I need routine. Currently, the daily checkboxes include writing in his diary, publishing a blog post, taking a walk, and reading a book.”

22.  Create a list of ‘joy things’ for the times you find yourself in a rut

When in a slump it can be difficult to remember what you enjoy or what can bring you back up from the rut. I keep a list of things in my phone, from listening to Tara Brach talks or playing the Everybody is Free to Wear Sunscreen. Both are free, can be done anywhere, and help me personally shift perspective, ever-so-slightly.

23.  Remember life is long

There is a pressure to rush to success, to be somebody in your 20s, to pave the way in your youth. But idolising early success can leave some feeling like a failure if they haven't “made it” by 30 – and what a shame when life is long, when there is such beauty in things taking time, there is so much surprise and delight to be open too.

Don’t close yourself off because you weren’t on a ‘30 under 30 list’. Success is determined person to person, not defined by the placement of a name on a list.  There is no such thing as a deadline for your ambition – things happen when the time is right, when you’ve had the time to develop, and often in ways that will surprise you.

As fashion designer Jenny Kee reminds us, “There are always surprises in your life and for me, the highlight is always coming.”

24.  Our productivity is not a measure of our worth

We don’t need to keep telling ourselves the story that productivity is a measure of our worth. Especially with creative work – be it a career or a project – we need to follow our whims, experiment, and embrace doing nothing at all.

I’m learning to embrace the moments I find flow, or manage to juggle disparate priorities, or the times I go off track and enjoy it.

25.  There is no such thing as balance, only balancing individual moments

Life is movement, not a perfect or stagnant balance. Rather than striving for balance, we can strive to master the art of balancing, which allows for more flux and change in any given moment.

26.  You will never get ‘there’, and that’s a wonderful thing

The problem with goals is that it’s easy and tempting to move the goalpost. We never arrive in life, things will always shift beneath our feet.

As Elisa Goodkind put it, “I don't think there is any such thing as a 'there' that you arrive at in life – you are constantly dealing with uncertainty and being thrown a lot of curveballs. But that is a really important part of doing what you feel is your heart and soul, you have to be willing to be in that struggle."

27.  Your weakness is your strength

If our greatest strengths can house our greatest weaknesses, the opposite can also be true. Found within our weaknesses, flaws, and imperfections is also a certain kind of strength. Our character can often be found amongst our vulnerabilities – and being brave enough to embrace them is often how we can be most creative, most ourselves, however vague and uncertain that search can seem.

In the words of Leonard Cohen, 'There is a crack, a crack in everything. That's how the light gets in.' 

28.  Putting things off can you teach you about what you really want to do 

Procrastination gets a bad rap, but I’ve often found that two things happen when I put things off: I am more prepared when I finally do something, or I realise I don’t want to or need to do that something.  

As Miranda July put it, “It doesn’t really matter if you were shit all day. Unless you were just on Instagram all day – surely there were some moments when you weren’t – so those goes in the bank and you are just accruing enough to build the brain that will be able to figure it out.”

Sometimes we are just not ready yet. “You can’t do it today, you are just not smart enough, you have to accrue more time pushing on that muscle before it will do this and suddenly you will have the whole idea. That is how it is for me – it’s a whole lot of misery but these days I just think, well, great, another miserable day in the bank,” Miranda July reminds us.

29. Don’t postpone your life

Perhaps what is more of a threat to our creative work than procrastination – which can be fertile ground for creativity – is post-poning the act of living our life. We might wait for when we have finished this, or when we are competent at that, but life is right now and we can miss that if we keep moving the goal post.

An extraordinary life isn’t something that is bestowed upon us when reach a certain number of accomplishments or acquire accolades – it’s when we finally learn to see that the ordinary parts of our days and lives are just as worthy of celebration as the so-called extraordinary successes.  

30.  We can’t summarise what life has taught us in a listicle…

But we can keep learning, from our mistakes, from our successes, from others, from what we’ve kept with us and what we’ve let go of. To leave us room to grow, learning – and relearning – is always best left incomple…


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Madeleine Dore