[Year in Review] Career reflections & lessons learned
Every year around my birthday, I like to reflect on the year that’s passed - and sometimes even further, like this year, all the way back to when I started my career as a freelancer and all of the significant things that have happened since.
I was born in December, so this timing coincides with the end of a calendar year as well.
2020 has been an especially strange year… but despite the global challenges that we’ve all been facing and a couple of notable personal ones too, career-wise, the past year has weirdly been pretty good.
Looking back, I realize that before turning 28, I’ve managed to cross items off of my long-term career to-do’s that I didn’t previously imagine I’d be able to do before my 30’s.
All of this makes me feel like I’m in a pretty good place career-wise and on track to keep on developing. At this point, I feel comfortable enough to say that I must be doing something right.
...and since I think about those things and usually write them down as well, I decided to also share those reflections and lessons here.
There’s just one more thing I need to do before I start and that is to share (very briefly) just what it is that I feel good about. I mean, who knows? Maybe what you’re looking to get out of your career is completely different from what I’m getting out of it, and my principles won’t be of much use to you.
On the other hand, maybe you’ll find them relatable and that will give you enough reason to keep reading to the end of a rather lengthy blog post. So what do I feel good about?
- I get to work with industry-leading, global corporations - but not in the “typical” fashion that many people around the world tend to avoid. I’m not employed, I’m a freelancer. My roles and the brilliant people I work with offer me a sense of creative freedom and space to make my own decisions.
- The projects I'm involved in are ambitious, creative, challenging and well paid.
- I've enjoyed both the time and financial resources to organize my own separate projects and business experiments (a successful TEDx event and a Private Label specialty coffee e-store).
- On a personal note, I feel a lot of gratitude for what I have, I generally feel at peace with who and where I am, which is not the way it's always been.
- I travel more than I used to and I'm in the best relationship of my life.
I'm really grateful for all of those things and I take none of them for granted.
Looking back, these are some of the key beliefs that I attribute to getting this far:
1. If I'm doing anything like everyone else, I like to wonder if I'm not doing something wrong.
We’re all very attuned to trying to fit in, to being “normal”.
It seems to me that we often associate being “normal” with doing something right.
I don’t see things that way. You just can’t try to be normal and hope to achieve anything above normal at the same time.
If you’re following in the footsteps of everyone else, it’s kind of silly to think that your results can be much better. At most, they’ll be incrementally better.
I’ll expand on this thought with an exercise, because we all have many theories that we believe, but fewer that we consciously and consistently act on.
This is one of those things where it’s important to not just believe, but act on.
So ask yourself, for example... What are you doing that’s just like everyone else in your industry, your role, or your community?
Then ask... is this really the best way to do things?
What would this look like if you could be 10 times as good? Is it sensible to work 10 times harder, or should you be looking for a different way of doing things instead? And if so, what may that different way look like?
2. Some people prefer to start things from scratch. I feel far more comfortable improving what already exists.
I thrive on knowing how to communicate the value of my work.
When something already exists, it's easier to measure the value of the improvement you bring to the table.
The more valuable the improvement, the more important you can make your position.
So I probably won’t be founding any startups anytime soon. But I’m happy to work with ambitious people who’ve gotten past the business validation stage.
3. Money will never buy you peace of mind. But ultimately, both are objectively important.
Some people hope that earning more will make up for their shortcomings. Others love to repeat the phrase that “money doesn’t buy happiness”.
I like to treat the two as separate but both important things.
I like to have money so that I can buy things, do things and go places. To foster peace of mind, I try to surround myself with people I like or admire, practice hobbies, try to better understand my own brain and occasionally practice meditation.
You really don’t have to choose between one focus or another (money or happiness). The two work pretty well hand in hand. In fact, I believe they work better that way.
Earning well is great. Earning well in a principled manner is harder but feels much, much better. It also fosters the kind of success that lasts longer.
4. Don't do anything you can automate or outsource at a profit.
We all have the same amount of time in a day. To do more than our peers, we can’t just work more. We need to work more effectively.
...to automate repetitive tasks (there’s a tool for almost anything these days) and outsource your low-value and time-consuming work.
Today, you can even outsource things like grocery shopping. I find that making a list and having someone else buy my groceries for me is a lot cheaper to pay for than with the cost of my time.
5. Ask better questions, because better questions = better answers.
The questions you ask invariably shape the way you think. Phrase them wisely, even when you’re only asking them of yourself.
“Why is this happening to me?” vs. “what can I do to improve my situation?”
This is a skill that podcasts can really help you get better at.
Listen to great interviewers. Pay attention to the questions they ask, how they phrase those questions, what the purpose of them is, what they’re trying to extract from their interviewee. Try to think of the questions you ask (whether outloud or of yourself) in that way.
For me, this exercise has been extremely useful. Asking the right questions during a job interview or in a discussion with a potential client can be the very thing that ultimately wins you that project or job.
6. Your expectations will influence your results.
You’re never going to get a job you don’t believe you deserve. A system will never work in your favor if you convince yourself that it is rigged against you.
You’ll never be great at something if you believe you just weren’t “born with that kind of talent”.
There’s a reason why all of this is true.
Oftentimes, we really are our own worst enemies. We pass down offers and opportunities because we think of the worst things that could happen.
We refuse to try things because we’re sure they will fail. We distrust people or companies whose help we could actually use.
In many cases, the “worst thing that could happen” never does, and in many cases still, even the worst potential thing isn't all that bad.
7. Few things can be as valuable (or destructive) as the relationships you cultivate.
At some point in my college days I developed a keen interest in behavioural and practical psychology which still hasn’t faded.
A belief that sprung from that interest and stuck with me because I kept stumbling upon examples of it is that we human beings are fiercely influenceable.
Our minds are influenced by everything and everyone around us - our diets influence how we think. Our thinking is influenced by how much coffee we’ve had, how bad the traffic was on the way to work, how good the weather is, how dark or bright the room we’re in right now is, the colors we’re surrounded by, the sounds and music we hear around us and… the people we surround ourselves with. Their thoughts. Their perspectives. Their values, fears, routines and every part of their daily activities that intersects with ours.
I’ve come to believe that it’s rather naive to think that we can choose to not let the things or people around us influence us. They do so subconsciously - and we have no control over our subconscious.
A phrase that I’ve heard Tim Ferris repeat on several occasions which I really like is this: “You are the average of the 5 people you spend most of your time with” (I could be paraphrasing).
I apply this principle very much in my own life - spending my time with agreeable people, people whose qualities I value, whose outlooks I admire - or with whom I can have a civil debate around ideas and beliefs that we don’t agree on.
The people we surround ourselves with influence the way we think, the way we feel, the opportunities that come our way as well as how focused or distracted we are.
8. Learn how to break down your larger goals into specific, measurable action items.
I’ve come to realize that many “ambitious-to-the-point-of-overwhelming” goals look a lot less scary when you break them down into smaller, more specific parts.
When you start to break things down this way, you may find that you no longer need to ask yourself if you can accomplish the “big goal”, but rather how long it will take to cross off all of the things on the list that need to happen before you can get there.
I find that this approach gives me a positive and, at the same time, a reasonably realistic perspective.
Once you’ve broken down your goals into the different elements needed to complete them, you can get to work on a priority list and a timeline. Which ones come first? Which are the easiest to accomplish?
If you have difficult objectives on that list of requirements that you’re not sure how to solve right away, what can you do now to start moving yourself further along in that direction? Into a position from which you’ll be able to solve that task later.
9. Complex problems are the best kind to work on.
Whenever I hit a roadblock and I’m not sure how to get past it, I like to remind myself… “This is why I’m here”. If it weren’t a problem, my help wouldn’t be necessary.
It’s normal to hit roadblocks. Finding a way around them is a great way to add substantial value to your projects.
Usually, the more complex a problem is, the more it’s worth to solve it. I get really excited about complex challenges if the right people offer them to me. This is an important nuance to keep in mind.
For example, to take a business that seems like it stands no chance of working, you could say that it’s a complex problem to try to promote it into a successful and scalable business.
Not if the product is bad.
Not if the founder (who has the most control over the company’s direction) runs his company in a misguided manner. Those kinds of “complex problems” are not the kind I get excited about.
...but an ambitious individual with a perspective that’s grounded in reality, who is trying to solve a complex problem that yields a real benefit for a specific audience, that’s the kind of person I really enjoy working with. That’s the kind of problem I really enjoy working on.
The world is full of complex problems… and we really need all of the people we can get to identify and execute effective solutions.
If there’s any one thought that I’d like to end this blog with, it’s this: being patient, avoiding shortcuts, playing the long game and taking a principled approach to developing your career, yourself and your finances all help to make life more rewarding - and successes more fulfilling.