Progress is addictive.
Especially when it’s public and people are watching. Progress is the cornerstone of the self-improvement bible. If you’re not growing you’re dying, they say. This conversation is missing one big part:
Sometimes you have to go backward to take an enormous step forward.
Losing everything to become anything
Gary Vee’s quote is the headline of this article. It made me think.
I’ve always been afraid of going backwards. I’ve lived and died by the approval of others. I’m a people pleaser at heart like a loyal puppy dog.
I want my masters barking with praise. I want their delicious scooby snacks as my treats. So I performed tricks for my masters like a good little dog.
I helped start a business that grew to over 100 employees. Family clapped. Friends clapped. Politicians clapped. Strangers did too.
I reached the pinnacle and thought I had everything. Then I stepped down. All of it felt like a nightmare.
I didn’t want to be the entrepreneur guy anymore. I didn’t even know why, other than I hated it. Importing widgets from China and selling them online was boring.
So I quit.
I took a huge step backward.
I had to sell the luxury car and live in less glamorous accommodation. How do you go from running a big team to being a solo contributor? No clue but I was about to find out.
I got a low-level job. I went from a $200K salary with stock options and everything paid for by the business down to $50K a year.
People laughed out loud at me.
I was the running joke in my friendship group, and as a result, I lost a lot of friends. I wanted them to stay but they didn’t want me. No longer high status or cool, they said. So I ran far, far, far away.
I became so distant from the people and places I was connected to that I shed my former self in secret — without me knowing.
Once all of the B.S. was out of the way, something new formed. My curiosity took me to wild places. From banks to airplanes that landed in America. From startup offices to coffee with weird venture capitalists.
There was no agenda other than to explore.
The step backward lasted for a while. I slowly built a new career over 5 years. Then I got the job of a lifetime helping Silicon Valley tech companies come to Australia.
Now I know the truth. That huge step backward was the step I needed to move forward and become someone I could never imagine.
Downsize the house to rebuild
A big house can be a burden.
Servicing all the debt is no easy task. If times get tough or you lose your job, then those monthly repayments can put the fear of god into you.
I got used to living in nice houses when I was younger. But my lack of income growth caught up to my lavish spending. The numbers didn’t add up. Even a high school math failure like me could see it.
So I downgraded to a student apartment next to a noisy train line.
The money I saved helped me put cash aside to invest in financial assets. Those assets generated their own income stream which supplemented my salary and still worked when I took holidays.
When friends came over to my apartment they weren’t wowed. It was a relief, frankly. We could focus on good conversation instead of showing off lounge suites and mancaves.
Sometimes finances get in the way. A smaller home can help free up much-needed cash.
It’s all a matter of whether your ego can handle it.
Downgrade your job title
I had one of those fancy Director titles at one job.
Colleagues thought my sh*t smelt better than Gordon Ramsay’s lasagne. They were wrong, though. I had imposter syndrome every day (a story for another day).
I met one guy who used to have a General Manager title. He was the big knob you wanted to take out for dinner and network with.
People were addicted to saying his name repeatedly.
Then a restructure came and took the title away. He went back to being a sales guy. From 50+ direct reports down to zero.
My boss laughed at him. “What a joke.”
I liked him. He had this interesting personality. He came to work every day with a smile despite the demotion. He didn’t seem to care one bit.
Eventually I changed jobs. We lost touch. Then 2 years later I looked him up in our company directory. He was back to being a big knob again. This time he was in charge of the digital strategy — everyone wanted this job.
The lesson here is he had to go backwards in job titles to rediscover himself. Returning to the frontline made him more relatable.
He learned insights from customers that being stuck in back-to-back executive meetings every day would never teach him.
Becoming single because you’re not in love
In 2016 I became a bachelor. Again.
I threw away a long relationship and settled for nothing. For the first time I had to join a dating app. No one went to nightclubs anymore like they did when I was 21 and ready to mate (daily).
Tinder was the worst.
I wouldn’t wish for my worst enemy to have to go on there. You’re a piece of meat on display at a digital butcher shop. You’re judged solely by how you look and what witty remark you make in your bio.
It’s hard to stand out when everyone loves the same things — walking, travel, my dog, family.
I tried to find love but it was a lost cause. So I stopped trying so hard. I took a few steps back. I stopped talking about myself and listened more.
Eventually I met “the one,” married her, and had a ball of poop kid. If I didn’t exit the bad relationship, I’m not sure I ever would have gotten married and had a child.
Trading bad romance for the single life is a good backwards step.
A step backwards often leads to happiness
That’s what I’ve learned.
A backwards step makes us humble. That humility is what helps us get out of our own way and find new wisdom we can tap into.
So why doesn’t everyone just go backwards and enjoy the process?
It’s not convenient. We want success now. No, actually, we wanted success yesterday already. Hurry up mailman and deliver it! You’re late. We live as if we’re running out of time.
We’re in a hurry to DO everything and BE everything.
If we slowed the heck down then that wouldn’t be the case. But with everyone flaunting their success on social media it’s hard not to feel behind in life. Like you should be further ahead.
And the dude that’s 25 and already a Lambo-driving millionaire only makes this reality more painful.
The other reason we don’t go backwards is that it’s hard. Our brains are wired for “easy.” We want to chase easy dopamine and then just get the hell to bed. Netflix, p*rn, and social media can deliver the dopamine faster.
It takes grit and determination to choose a harder option. The rebuild phase is tiring, and we’re already so tired from the last 3 years of culture wars and political drama. So we don’t go backwards.
We stand still. We stay where we are. We die slightly inside. We become a lifeless, soulless zombie stuck in some kind of Keanu Reeves Matrix.
It doesn’t have to be that way.
Lower your ego. Forget about outside opinions. Choose to go backwards so you can gain the wisdom to make giant leaps forward.