Finding Motivation For Meaning.

What does it mean when I have all the freedom I want but I'm not tap dancing out of bed in excitement?

Whether its reading autobiographies or listening to interviews of people I admire, I'd hear similar phrases all the time: "tap dancing to work", "jump out of bed in excitement", "building your ideal day" etc...

Naturally, upon choosing to give myself what financial freedom would buy: freedom of location, time and direction, I proceeded to built this out.

I approached it from every way from crafting the ideal day filled with all the kind of work that made me happy, to avoiding the key things that made me upset. I was reading, writing, thinking, training every day while traveling and working out of the coffee shops I wanted.

But I rarely ever felt like I was "tap dancing to work" nor did I ever "jump out of bed in excitement". Rather, I think I've felt extreme levels of anxiety, depression, euphoria, hope and everything in between from end to end.

The emotional roller coaster was a constant. What I wanted was the excitement to be somewhat consistent but this never materialized.

Yet, I continued to carry on. I don't know what my friends imagine when they say: "You're so lucky" or "I wish I could do that". From the moment I wake up to the moment my brain shuts off, my head is buzzing with all the things I need to do. I've worked 100-120 hour weeks in a windowless office stinking of takeout Chinese food before and that was easy compared these days. Granted I'm not miserable anymore but I'm not elated every fucking second of it either.

"Happiness" ceased to be a vocabulary I used. People kept on asking me if I was "happy" and I just stared at them with a "what do you mean?" face.

I'd wake up in the mornings hitting the snooze button and going back to bed. Waking up an hour later feeling defeated for failing to wake up early. I'd procrastinate on major projects and find any reason I can not to send important emails. All these feelings and unmotivated behaviour constantly shocked me and made me question if I had made a mistake going down this path of my journey.

Sure, I get that it's naive to think every day will be butterflies and roses but shouldn't there be a majority of consistency? Am I just doing something wrong?

The Theory of Why My Days Aren't Roses and Butterflies.

Maybe I am wrong. Or, maybe the number of "exciting and motivating days" is limited as a function of 1) What you know and 2) Options given structure

Let's put it this way:

When I was in accounting, I'd say 1 out of 10 days I would be excited to go to work. The one day might've been because I'd be doing recruiting or grabbing coffee with someone. I didn't even fathom that quitting the firm or even leaving the profession was much of an option. I had a very limited scope of what was out there and the best case was probably 3/10 days of excitement here.

In consulting, it got a little better to 3 out of 10 days. It would depend on the project I was on but most of the times I would just be excited to grab coffee with friends on the Fridays. I had expanded what I knew though. I knew there were more options out there in the world. I also learned I how to be effective with each hour as well. It probably increased the max range to 4/10 days.

In investing, it was about 5 out of every 10 days. Mainly, the excitement would be on days of exciting meetings. This was the dream job from all the options I had considered. But even then, I felt the max would be capped at 6/10 for me. I mean, I was still an employee and I felt the vast difference between an equity holder and an employee.

I've previously written about the 5 key motivation factors being: autonomy, ownership, learning, feedback and environment. With each transition I saw improvements on these areas as I changed and the profession changed. However, there seemed to be a hard line I just couldn't get across.

But a limitation on the upside also indicated a limitation on the downside too.

The rigid structure presented in the form of "employment" provided me with a safety net where my exciting days would be between 3 - 6 days out of 10.

There is a limited upside but also a limited down side. Because you are playing within the structured confines of an environment and excitement comes as a relative function of what your available options are.

Hence, a coffee meeting with a friend can make you jump out of bed if the alternative is a windowless dimly lit audit room by yourself.

But what if you expand horizon of options? The structures are now soft and within your control. This "freedom" people are so envious of but is oh so scary and dangerous to actually wield properly.

Such freedom actually opens up the possibility of having 0 out of 10 days be exciting for a long time. But it could also present the option of 9 out of 10 days being motivating and exciting as well.

As I've been writing this, Seth Godin's book, The Dip comes to mind. Godin talks about how every entrepreneurial or "worthwhile" venture starts off with immediate highs. Everything is exciting. We are talking 6-7 out of 10 days being exciting here. I think this was actually the case for me as well as I created OMDV. Then we get hit with the "dip". A plummet of the stock price. But only by going through this period (can be short or long but I think the severity and duration may be correlated with the difficulty and unconventionality) of being in the dump with 0 days of excitement (maybe even negative on those days when you think jumping in front of a truck might end it all) will there be the potential to experience moments where 8-9 out of 10 days are exciting.

Continuing with my over-generalized example based off of sample size of n=1 (yours truly), a limited environment may yield 80% of your years having 3-6 out of days be exciting and motivating. Conversely, this weird journey I'm on may lead to 80% of the years having 0-1 out of 10 days be exciting. But there is the empirical faith that the latter days will be moments where 8-9 out of 10 days are exciting.

Thinking back, I think majority of the individuals labeled as "successful & etc..." suffer from a recency bias when they think about the mix of their days. They may be accurate in saying that most of their days now are filled with "tap dancing" to work. But I can imagine that 80% of the 10-20 year journey for them could have been filled with days of 0 motivation.

Maybe it's wishful thinking on my part as I grasp on straws to continue to push on.

What Can I Do?

In his book, The Messy Middle, Scott Belsky (Co-Founder of Behance, VP at Adobe, Benchmark VC) talks about celebrating small wins to keep pushing through. Oh, and the 'Dip' Godin references is practically the same thing as Belsky's Messy Middle. It's just the shit period really.

For one thing, reading those books hasn't really made going through this period any easier. Maybe it's good to know that it's a thing and that there are really no answers for it other than to push on.

But, like every person out there, I feel like my situation is unique. I also have the confidence to be the small % that can make it work but am also worried about the 80% (or whatever large %) chance it won't. I want to think it's all up to my own propensity to continue pushing but sometimes it's not. I'm sure this is a very average thought that most go through but I figured I'd share my very average thought.

I think any ambitious, over-achiever persona can relate with the disgust you feel with yourself for not spending every hour of your waking day being productive and effective. Even after having deleted all kinds of social media off my phone since February of 2019 I still find ways to procrastinate at times. Just awful. This resentment towards my inability to be superhuman, this anxiety for not producing the results I want, the frustration at the world for being oh so illogical and difficult. Just an awful way to be.

So what then?

I'm going to try to celebrate the small wins. I really am. I'm going to really try to push that ego down and get humble and be happy about sending out 1 email a day or writing 1 sentence a day. Try to celebrate that I at least took one step (even if it might not be the most effective and efficient step).

As cheesy as it sounds, I'm also trying to pat myself on the back too. Sure, the devil in me will come out and call me an idiot for celebrating nothing worth celebrating. But maybe if I pat myself enough it'll work. I did fear that celebrating small wins would make me negligent but my parents reminded me that never seemed to kill my drive. So it'll probably be for the better if I learned to actually accept myself and love myself for once.

I've always been confident. Maybe even overly-confident. But I think that's very different from loving yourself. People think confidence is a form of narcissism but I disagree. I think it's something entirely exclusive that needs to be worked on. At least it is for me. With the assumption that my problems are probably quite average I'd wager this to be the case for most.