Next week we’re up for two Plutus Awards for Podcast of the Year and Best Millennial or Gen Z Blog. Because whether we win or lose our readership may potentially rise, I figured this is the optimum time to level-set expectations for our new visitors.

Please enjoy…

I Have No Idea What I’m Doing Here

I am speaking for myself. Perhaps my cohost @IamRichJones knows exactly what he is doing with his life. In 2019, I found myself stressed the hell out (for no logical reason). In fact, I drafted this piece at 5 am after waking up from sleeping, but to say I was ever really “sleep” would be an insult to sleep.

I was used to the pattern of fitful 8-hour nights choosing between insufferable and insomnia. If my inability to sleep through the night was any indication, I might not have been as over THE EVENT as I pretended. Like the extended hangovers of my 30s (they last all day!), just because the source is gone doesn’t mean there aren’t residual side effects to remind me.

This is why I don’t like the title “expert.” For example, personal finance expert Kevin O’Leary said he doesn’t waste money on coffee, then later admitted he spends thousands a day on food. Personal finance guru, Suze Orman, chastized millennials for wasting money on coffee, then admitted she sometimes struggled to pay for…the costs of her private island. To say the least, the gaps in logic between these personal finance experts’ expertise is exasperating.

I’ve found myself in a personal finance community bubble before. The only skill I’ve proven to have when it comes to my “expertise” is an uncanny ability to repeatedly self-sabotage and somehow recover. Labeling me a “personal finance expert” for getting out of the debt I got myself into in the first place is like congratulating a smoker for quitting, again.

It’s a milestone, but is it really an accomplishment? Personal Finance is hard because the math is easy. It’s the behavior that trips most of us up, even the so-called “experts.” It is easier to know better than it is to do better.

One interesting survey even found that 46 percent of financial planners don’t have retirement plans themselves.” – Dollars and Sense

Nevertheless, the title was bestowed upon my shoulders, and I failed to object. Vanity is quite the seductress! And so I ran with it; only to learn later that with great power (and made up titles) comes great responsibility. I liked the power part. I didn’t care so much for the responsibility.

Fake It Til You Make It Works Til You Fail

One day recently I self-diagnosed an internal conflict between my expert title and my reality. I was living a lie. I wasn’t lying to anyone in the literal sense. I was lying to myself. The lifestyle I lived and the lifestyle I preached online existed in conflict.

Every week I hopped on the Paychecks & Balances podcast and told the P&B Family to “be a part of the change you want to see,” then I packed my mic up and went back to living a life of conformity. I encouraged people to “pursue their dreams” and “take a chance” and other meme-worthy quotes. But as soon as the show ended, I promptly logged off and dove back into the waiting arms of my 9 to 5. We did interviews with inspiring individuals making hundreds, thousands, and in some instances, millions a year. I told our listeners, “see you can do it too!” 

This is the Millennial conundrum, which is the worse fate: to remain sitting safely, but obscurely, on your butt, or to put yourself out there only to fall flat on your face and become a viral #FAIL meme?

I Was Scared to Fail and Terrified to Succeed

What would happen if I put my money where my mouth is and I couldn’t even spit back enough spare change to support myself? My internal fear monger was eager to seed further self-doubt: You’ll be broke within the year. Hell, the month! You make perfectly good money at the day job. Why take a chance on yourself?

The voice was right.

I was making good-to-great money simply following that tried and true traditional career path. I didn’t need to rock the boat. This is exactly what I pursued, right? Isn’t this why you went to college? What will people say? What will people think? Who are these “people” we’re worried about? I still have no idea.

The trade-off for “success”?

There was the happy, carefree, post-work me the podcasts and friends know and love. Then there was the guy who toned it down, code-switched like an X-men character, and did whatever he had to do to ensure the security of the next paycheck was intact. You may recognize people like me in public draped in their work-approved costumes: covered up tattoos; empty holes were piercings hang during happy hour (notice this happy hour is after work hours); their creativity stifled for the common good.

It takes a village to break a spirit.

After 15 years in the game, I was well-trained too. I learned to turn down the volume of my full expression of self for 8-hours. I smiled even when I didn’t feel like smiling.

  • On Monday, I joked about “a case of the Mondays” on the elevator ride up;
  • On Wednesday, I LOL’d right on cue at ‘hump day’ jokes occupants had all heard 100x before; and
  • I even feigned a believable celebratory glee as we all sighed “whew, we made it!” on the elevator ride down that Friday.

Our collective rewards? A two-day reprieve mandated by some lost civilization predating our grandparents and fossil rock. Yet, somehow these invisible hands still guide our every movement right up to the present day.

Rinse. Recycle. Repeat.

That’s what people are supposed to do, right?

Why Do I Struggle to Follow the Rules

To be fair, the job didn’t do anything wrong. No one “wronged” me. Their only grievance was to do what most jobs do: suppress ambition in favor of maintaining the status-quo for 40-hours a week, 52-weeks a year.

They pay you to do it! You should be grateful you even have a job!! It’s not the job’s responsibility to fulfill your passions!!! You aren’t anyone special. I know. I already told myself all those things, more than once.


I blame no one other than myself. Although it would be nice if it was somebody’s fault. At least then I could find temporary relief in finger-pointing and deflection. As the years added up to decades of time served, I continued to pretend I still didn’t know what to do.

But, I had less of an excuse than the average worker.

It was our business’ mission to “help millennials make money, save money, and get out of debt.” I authored an entire series spotlighting people who looked like us doing awesome things in personal finance and beyond.

“You guys fill an underserved niche!” marketers exclaimed. We had hundreds of “five star” reviews to validate their claims. Our words inspired thousands every month! And, in the face of all this evidence to make a change in my own life, what did I do? I kept right on taking the safest route possible. 

There were no haters holding me down. Only people actively lifting us up; living vicariously through us, waiting for us to make it big. I watched others with more courage than myself take a chance at the plate and Glo Up in the limelight. But, instead of running up to knock it out of the park with them while the fan’s cheers were the loudest, I stayed in the shadows convincing myself I’d only strike out on the big stage.

More years passed.

Hey, at least I had those safe, dependable 9 to 5 checks to cash in, right? And, all they cost me in return was to give up on a dream. That’s a fair trade.

Plan for the Worst, Hope for the Best

Another year has passed on the calendar.

I know, because FinCon 2019 is here, again. I love FinCon–an inspirational conference where money and media meet–filled with like-minded #MoneyNerds trying to make positive changes in their lives too. I had been attending since 2016. It’s been a game-changer in my vision and inspiration.

However, it is also an annual anniversary of all the unfilled Calls to Action since we last met. Like that dream business I still hadn’t started.

This year’s anniversary gift?

A reminder that I spent another 365 days vehemently fighting to snatch defeat from the jaws of victory. I managed to spend excessively on everything but funding my entrepreneurial dream.

Feeling no less terrified and like a fraud than I did since the last time I showed up to the conference without my own brand incorporated and flourishing, I decided to see if the domain I wanted last year was still on sale. Maybe, if I was lucky, someone already bought it. Then I could blame that anonymous stranger for my failure to act.

They hadn’t. Dammit. Foiled again.

I was out of (good) excuses. I was tired of feeling like a hypocrite. I logged in to my account and finally purchased it. It took 5 minutes and around $20. I’d spent more on drinks across nights whose memories I couldn’t recollect if you paid me to. Oh well, no more excuses, but I’m sure I’ll think of some.

As usual, my timing is impeccable. A decade earlier I began my job search in what turned out to be the worst recession since The Great Depression. In 2019, I stop procrastinating and plan to launch a business just in time for the next recession after the longest expansion ever recorded. I guess I like a bit of a challenge. It’s a good thing I’m not a gambling man.

Related: How to Recession-Proof Your Personal Finances

I’m running right on schedule, yet it always feels like I’m lagging behind. It’s hard to negotiate with feelings. They are not known for their logic. But, I will press forward anyway. Now it’s time to be a part of the change I want to see.

Use your 20s to learn. Your 30s to apply. And your 40s to teach and pay it forward. – a Mentor of mine

That night I slept better than I had in months.

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