This is the top – or is it?

I’m worried I peaked somewhere mid-pandemic. Time to fix that.

Humor is a powerful tool. Every day, I use humor to deal with the mundane, dark, and difficult parts of life. Making my clients laugh distracts them from emotions that can cloud their judgment when making uncomfortable decisions. But making people laugh distracted me, too.

During the darkest days of the pandemic, I found an audience in desperate need of comic relief. My Twitter community grew through consistent joking about the economy, crypto, world events, and more. I used humor to cope with my own anxieties about the uncertainty we faced. I connected with thousands of new people online and gained many friends and a fair amount of business. For a while, I thought I cracked a code: Doug makes a joke; Doug gets laughs; Doug gets followers. The dopamine felt like a warm hug. It still does. 

In truth, I’ve leaned too heavily on that instant gratification. I have not been creating thoughtful, original content like I used to. Sure, my tiny headshot still pops into your feeds, and you might hear me as a guest on someone else’s podcast, but I have not been leading the conversation. Some followers don’t even think I am a real person.

At this point, I feel like a meme of myself.  

How can a guy who wrote a book with his wife when they had a newborn at home be the same guy who came to think the easiest thing would be good enough? 

I can identify two reasons. First, I was burnt out. Because my schedule was so flexible, I turned it upside down in 2020 to accommodate our children being home. In the neighborhood, I became known as “the dude with the stroller on his phone,” filling my mornings with media calls and Twitter Spaces, followed by often-interrupted transacting in the afternoons and client Zoom meetings late into the night, every night. I am incredibly proud that I could support my family and still grow my business, but once I entered triage mode, I never really came out. Just this fall, my wife asked me why I still opened my calendar for night meetings every single night, and I didn’t have a good answer. Taking a step back, I realized I was not working in an efficient or healthy way. I was no longer in control of my schedule, which in turn, ate up so much mental space that I couldn’t create much beyond a tweet. 

The second reason is quite personal: I have a deep fear of rejection. Growing up, this played out as a form of social anxiety, where I would talk, and talk, and talk about myself, making sure everyone on the receiving end of my diatribes had enough information to accept me. I came off as intense and self-absorbed, but at least no one would think I wasn’t good enough. Perhaps you can see how someone like me would cling to the gratification of banger tweets rather than welcome the vulnerability of taking a stance through more thoughtful content, which comes with the risk of being criticized. The larger my audience grew, the more concerned I grew over what I put out into the world. I know how silly this sounds, but I didn’t want to run afoul of anyone–not one follower. Admitting this is forward progress on a journey I’ll continue throughout my life. 

The timing couldn’t be better; and no, I don’t mean because Elon Musk had many of you pushing out your final tweets like the Titanic was sinking. My wife, Heather, joined Bone Fide Wealth as its Director of Business and Legal Affairs, which is facilitating a major shift in the way I operate and prioritize my time on outside business. I am inspired by watching her grow her beautiful newsletter, Our Tiny Rebellions, which searches for meaning in life’s little wins and losses. I may not have seen it for a while, but deep down, pausing my blog due to the pandemic, old habits, and even from my objective success, was a loss of my own. 

It’s a shame to build a community just for laughs. I want to entertain you, but I also want to make you think. 

Here’s the plan: I will be writing my newsletter again, but the Invest In You newsletter is now This is the Top. As one of the youngest financial advisers to focus on millennials since the Great Recession, I’ve had an intimate look into my generation’s evolving perception on money, success, culture, and family. We’ve only been adults in unprecedented times. When we proclaim, “This is the top!” are we really asking, “Is this the top?” Will the market keep flourishing? Is this the peak of my career? Am I wasting or savoring the best moments of my life? 

We will also laugh. Of course, we will laugh. 

I hope you will join me by subscribing. For now, signing up for a free subscription will mean one email per week. I hope to expand into additional content and paid subscription benefits in 2023. 

Speaking of additional content, keep an eye out for my weekly personal finance show called “Funny Money,” which I plan to host on YouTube and Twitter Spaces. You can also expect more content across other platforms like Instagram and *maybe* TikTok. 

I am excited and nervous–I will get some things right and a lot of things wrong. But at least when I ask myself, “Is this the top?” I’ll know the answer is no. 

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