Updated February 1, 2023
When I got to Ottawa, I found that everyone had ideas about how to be successful. Friends told me that I should get a job as a policy advisor in a cabinet minister’s office or for a politician. In some ways, these jobs would be perfect for me. I thrive on relationships and love networking. I don’t mind schmoozing a bit.
They’d tell me, “You’d be perfect for those jobs.”
But there’s a catch. These jobs mean working in downtown for 60 hours a week, long hours of overtime spent in the office clarifying a policy position or checking a speech. They’re cut-throat races to the top, and usually, the ones who spend the most time in the office win.
I have three amazing daughters at home. I’m not interested in missing their childhoods. They are the most important thing to me, and I make my career decisions based on whether it fits with my kids.
Success means a lot of different things to different people. And sometimes we wake up in life and realize that the success we’re chasing isn’t ours. And sometimes we need to learn how to be successful no matter what life throws at us, because it will throw us some curve balls.
In this post, I want to share what I’ve learned about how to be successful. I hope these steps help you on your journey. Good luck!
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1. Don’t chase other people’s success
I’m an oldest child. I care way too much about what people think about me. And part of this has always been doing work that is seen as impressive by those around me. I want to be respected.
But part of my personality is also that, in order to do work that impresses other people, I will do things that make me miserable. I hate it, but it’s the way I’m wired. Or, even more dangerous, I will do things that I don’t mind rather than things that I love.
So, I’ve stayed in some dangerous, god-awful jobs that I hated, but that other people thought were good jobs.
The thing is, I’ve loved blogging more than just about anything else I’ve done. Part of my success definition will mean being a successful blogger. And to my surprise, this year I was able to earn my income online and make up the difference with consulting.
But who the hell is going to understand that? Almost nobody!
Tell people you’re a blogger. I dare you. They’ll think it’s ridiculous.
I told someone in an interview once and he said, “Oh that’s nice. We all need a hobby.” Doing this work fits nobody’s definition of success (nobody I know anyways).
So here’s my question for you. Are you following your own definition of success? Or someone else’s?
Here’s what I used to think success was:
- Important work
- Wearing a suit
- A pension
- Name dropping
- Access to powerful people
- Letters after my name
Now? My list is totally different:
- Picking up my kids from school
- Earning passive income so I can do the things I care about
- Traveling the world
- Using my extra time to follow my pipe dreams
The bravest thing that you can do is be true to your own calling and own up to who you really are, so before you break your neck trying to either become a tenure-track professor, a CEO of a start-up, or a government employee with a great pension, you owe it to yourself to ask yourself whether you are chasing your own definition of success or someone else’s.
2. Keep improving Plan B until its better than Plan A
We all have to go through disappointments in life. I thought I would be a professional musician when I was 17. Some kids want to be famous athletes.
Life is full of broken dreams.
Put that on a bumper sticker.
Most people don’t just have one broken dream. They have a trail of things that didn’t work out.
Letting go of my dream of being a professor was the last in a long line of things that didn’t work out.
I’m not particularly religious, and if you asked me—a very serious academic who studied religion as an anthropological and sociological discipline—whether destiny or fate is real, I would probably get tongue-tied.
How the heck should I know?
But whether you believe that God, or the universe, or whatever directs you towards your calling, or whether you just instinctively know that sometimes humans end up where they never expected to be and that’s okay, sometimes there’s beauty in turning your Plan B into Plan A.
Or, to put it better, keep making Plan B better until it’s more attractive than Plan A.
Grow plan B. Nourish it. Make it more audacious.
The reality I’ve found is that your dreams can expand rather than shrink. So don’t fixate on one dream. Keep building bigger and better ones. And make Plan B so great that Plan A pales by comparison. That’s how to be successful.
3. Know what you really want
Why did I want to be a professor? Truth be told, I wanted to travel around the world. It’s what I’ve always wanted. I’ve got a wanderer’s soul. When I was 17, I played in a heavy metal band and I wanted to tour, living in the back of a van with seven other sweaty, smelly teenage dudes. It never (really) happened.
At the heart of this was my desire to have adventures. I’m the small-town kid, raised poor in the woods in Northern Canada, who always saw the outside world as some untouchable—yet exciting—place.
And when I met my doctoral supervisor, he flitted off to Israel, New York, or Belgium every other week for an important conference. I thought I had found my calling.
I enjoyed the work and the research. But I loved the travel. (I wrote a bit about it in this post.)
And once I had lived in Nice, Berlin, and Athens for my PhD work, I realized what I was really chasing. It wasn’t the tenure track. It was an adventure.
What about you? What does your internal voice tell you? What is pushing you toward your dream? Do you stop to think about it?
Life’s so damn short. So please, God, don’t spend yours chasing something you don’t want. I’ve watched my generation chase jobs, houses, spouses, kids, and lord knows what else, only to wake up 15 years later and realize it was never what they actually wanted.
Save yourself time. Figure it out now.
4. Pay attention
One day, working at the government, my colleague needed a slide done for a presentation she was working on. We had some branded graphics she was trying to reproduce, and she didn’t have the time for the communications dept. (comms.) to do it. I offered to try, with the limited government computer programs and no access to Adobe Creative Suite (my favorite set of programs in the world).
I opened up PowerPoint and made a fantastic graphic.
Halfway through, a fellow policy analyst came and watched. She saw the smile on my face. “What are you doing?” she asked.
I looked sheepish. “I’m designing a slide for Kate. Comms doesn’t have time.”
She laughed, “you actually look like you’re enjoying yourself.”
I thought for a minute, as it dawned on me. “I am. This is actually something I love to do.”
“Really? I always thought comms was for people who weren’t good enough to do policy.”
I thought about what she said. That week I’d spent time advising high-level members of a foreign government on refugee policy. I’d written another document that was in the process of being signed by foreign cabinet ministers.
And yet the happiest thing I did that week was making that slide.
I wanted a career that let me be creative. Working for the government was NOT that.
What did that teach me? Pay attention to what you spend your time doing. The stuff you seek out. The stuff you enjoy.
5. Analyze the values behind your goals
Analyze yourself and try to figure out what drives you. What really drives you? Are you being driven by your healthy dreams or by your poisonous fears of inadequacy? Is your life on autopilot, or are you still driving?
These are important things to ask.
Try this. Sit down with a piece of paper today and write down some things that you think success is for you. YOU, mind you. Not other people. If it’s helpful, you can even write a list of things you are doing to appear successful for other people that are NOT EVEN THINGS YOU WANT.
I’ve been there. I see you.
Get specific about what you want, and why you want it. Then try to identify a career goal that connects to what you want.
Here’s my list:
- I want to spend as much time with my spouse and my kids as possible. Functionally, with my kids, this means picking them up off the school bus, reading them stories every night, and going on adventures with them. This is my definition of how to be successful as a dad. Career Goal—Flexibility
- I want to be a writer and speaker who reshapes the way we think about education and who teaches people how to build amazing lives with the degrees they have. This means interacting with government and policy leaders on a regular basis to drive better education policies forward. But more specifically, it means becoming a thought leader who speaks to students and helps them build amazing lives. Why? Because this makes me come alive, and because I felt there was no one to help me turn my degree into a career. Career Goal—Impact
- I want to be a world explorer, living in different countries and learning languages as I can. I’ve lived in Greece, Germany, and France (and speak those languages). Next, I want to spend at least six months living in Italy with my wife and kids. These family adventures have been the best part of life. Career Goal—Adventure
- I want to build a house for my family that’s not too big, but that’s in the woods somewhere. I was raised with access to the wilderness, and I miss it. It nourishes my soul. Career Goal—Inspiration
These are just a few of my many goals. But take a look at the words I’ve written next to them.
If I’m honest, these are the things I’ve been chasing my whole life.
The mind-blowing thing about seeing my goals through this lens is that there actually is no Plan B. I’m still chasing the things that were Plan A all along. I just didn’t know what they were.
6. Choose the right role models
People freaking love Elon Musk. And that’s cool. I think he could be a great role model for a scientist-turned-entrepreneur. But I’d have to have my head smashed on something to ever think he should be a role model for me as a father.
So before you compare yourself to Elon Musk, or Bezos, or Jen from your high school who’s killing it, ask yourself… Are they even where I want to be? Do I even want what they have?
I mean, we all want to get wealthy… duh. But do you really want to spend 100 hours a week in the office, or be off hustling somewhere and miss your kids? Maybe you do. I don’t.
So Elon is not my role model. I’m picking someone who’s made moderate wealth, but who’s also a really good dad. That’s worth it to me.
7. Master the pivot
It’s a few years old now, but I read Jenny Blake’s book Pivot when it first came out.
In a world where most success stories start with someone quitting their job, leaving their spouse, and going to Italy — okay, that’s Eat, Pray, Love — sometimes it’s the small steps in the right direction that matter. Instead of the wild shot in the dark, can you take measured, intentional steps toward where you want to be?
It’s hard to believe, but that’s a better recipe for how to be successful than dropping everything and coming crawling back in a few months.
Conclusion
Whatever your goals are, take the time to get down on paper what you want and why you want it. Be as specific as possible. Why do you want the things you want? What do you REALLY want? Who can you emulate? And what tiny steps can you take to get there?
What do you think being successful means? I’d love to hear it.
Now Read: 9 Steps – How to Find a Job You Love
