250: Do what you love and the money will follow . . . IF you meet at least 3 of these 20 criteria (Rolling in D🤦🏻‍♀️h)

This episode is brought to you by State Farm. Listening to this podcast Smart move Being financially savvy Smart move. Another smart move Having State Farm help you create a competitive price when you choose to bundle home and auto bundling. Just another way to save with a personal price plan like a good neighbor, State Farm is there. Prices are based on rating plans that vary by state. Coverage options are selected by the customer. Availability, amount of discounts and savings and eligibility vary by state.

Sometimes, despite your best efforts, you simply aren't good enough at your chosen work, love, passion, income. Or you're not good enough in time or you're good not great. While attempting to thread the needle of a winner take all industry that's also experiencing a significant rise in big conglomerate competition and consolidation. So you pivot and you right size your goals and you regroup. You connect with a new crew in the meantime, the ones who are at least happy to hear about all your perils and pitfalls along the way. Just as long as you keep getting back up.

This is your time. How can we earn twice as much in half the time with joy and ease while serving the highest good? That is our guiding question here at the Freetime Cafe, your home for Heart Based Pieces business. I'm your host Jenny Blake. Join me for conversations with authors, friends and fellow business owners as we explore ways to free your mind, time and team to do your best work. Now onto today's show.

Welcome back Free Timers. I'm excited to share another crossover with you today from one of my Rolling in Dough essays. That's my paid substack. I'll put the link to subscribe in the show Notes in case you're not over there already, this is one that I really had a lot of fun writing. Came out toward the end of November in a moment of exasperation with trying to pursue the creative path and not only do that while living in New York City, but also supporting a household which includes three of us, Me, Michael and Ryder. And that's exactly the premise of rolling in dough and why I started it in the summer. It was to write about that very pressure cooker of being the breadwinner. Trying to do that while sustaining a very custom, particular heart based, delightfully tiny creative business and doing it in what I would consider a very wonky economy for small business owners. Maybe the headlines and big companies. People who work for big companies are doing just fine. But I know amongst my solopluspreneur friends and I, we're feeling the pinch. So I hope you enjoy this crossover essay reading it here for you. And, you know, don't get too depressed about it. It's meant to be a little bit tongue in cheek, but kind of speaking to the challenges, or at least saying them out loud, because I'm someone who always wants to think for the best, and I'm kind of like Jim Carrey in Dumb and Dumber. So you're saying there's a chance, and no matter how small, I do think there's something to be said for pursuing dreams, even when they seem very far away. Without further ado, here's the piece.

Do what you love and the money will follow if you meet more than three of the following 20 criteria By Jenny Blake November 22, 2023 do what you love. The phrase is emblazoned at WeWorks across the globe. Enlarge neon lights across lobby walls, bedecking laptops via swag stickers and printed in playful cursive on the mugs that facilitate bottomless free coffee with the addition of Always in small print at the top. But what becomes of the adage to do what you love when the company blasting it everywhere declares bankruptcy? As the Associated Press reported two weeks ago, WeWork has filed for Chapter 11 bankruptcy protection, a stunning fall for the office sharing company that once promised to upend the way people went to work around the world. The filing comes at a time of incredible disruption in the commercial real estate market. The COVID 19 pandemic led to a spike in vacancies, and major markets from New York to San Francisco are still struggling. But it was an aggressive expansion in WeWork's early years that led to the bulk of its current troubles. The company went public in October 2021 after an attempt two years earlier collapsed spectacularly. The debacle led to the ouster of founder and CEO Adam Neumann, whose erratic behavior and exorbitant spending spooked early investors. I followed this incredible rise and fall across every single podcast, TV series and book. I read and listened to everything I could find in a ravenous fit of schadenfreude. If you're noticing a pattern, yes, I will admit I can't stand actual true crime shows. I would never sleep or leave the house. But true business crime based on Icarus like ambition, charm and manipulation, I am putty in producers hands. From Billy McFarlane to Elizabeth Holmes to Travis Kalanick to Adam Newman to Sam Bankman Fried. I do enjoy seeing business hucksters serve their just desserts. If what you love involves defrauding people, manipulating others for personal gain, or playing dirty. Please do not do more of it. But what about the rest of us? To start by stating the obvious mindset wise, the viability of doing what you love and the money following differs by generation. I asked ChatGPT how each cohort might react when applying this phrase to career pursuits. Generational stereotypes are just that, we're all unique snowflakes. But allow me to summarize. Generational reactions to this adage might sound something like the greatest and silent generations. You've got to be effing kidding me. Get back to work baby Boomers. Fat chance kid. Find a good stable job to fall in love with Gen X. I guess if you have a day job while also doing what you love.

Look, this person on the Internet did it. So can we.

Crying emoji Gen Z Do what you love as an influencer and the SpawnCon menu will follow. Gen Alpha does TikTok scrolling count? In all fairness, it's too soon to tell. They were born after 2010, so the oldest are only 13. At that age I had a triple whammy of braces plus headgear at night, glasses and an inhaler. Being an elder millennial myself, by 2020 I had just been sailing through 10 years of a wildly booming economy during the same 10 years I launched into self employment. That means I had mostly been successful in pursuing my various passions, or at least independently groping around to find them, when the pandemic hit. After 80% of my income was wiped out within the first two weeks of March, accompanied by news headlines of people dying all around me in New York City, it was with full millennial passion scales over my eyes that I decided to double down on all the cliches. Life is short. I am going to car pay that dm. Every damn dm. I will do even more of what I love and the money will follow. And then I have a bunch of crying, laugh crying and then melting emojis. In all seriousness, I did stop doing things that were draining my energy and that also weren't producing positive results. I loved speaking gigs, my steadiest source of income for the previous 10 years, except they had all but dried up. So I decided to go all in on a new direction. A book and podcast to follow where my heart had been for a long time. Small business owners with delightfully tiny teams. I wrote FreeTime in 2021 in a state of near hermetic bliss. I finally got out of the way of being a bottleneck in my business and went pro on my two podcasts by hiring a wonderful production company One Stone Creative, the best outside team I have ever worked with. Everything about podcasting filled me with glee. It still does. Preparing for interviews, conducting them, connecting with guests, getting feedback from listeners. One year after launching the show, was nominated for a Webby alongside four heavy hitters in the business category that had massive budgets and institutional money behind them. Mine was the only indie, and I was so proud to represent small shows. I can honestly say that while podcasting I feel I'm adding unique value in the world, operating at my highest and best. When I decided to go all in, I'd been podcasting for seven years. Surely that was enough time to take a flyer on making it a more significant part of my business goals for the next two. Not much else was popping anyway. For the first time and for the last two years, I was working precisely in the strike zone of my supposed zone of genius, doing activities that truly fueled me. Except just one problem. The money didn't follow. At least not in a big enough way to support a household. And or at least not yet. In contrast to 2020, I'm now out of financial Runway and more tired. Having weathered these last three years of dumpster fires and having tried so many things that didn't work. Instead of gaining unstoppable momentum via book sales and podcast downloads, my business Flywheel has all but sputtered to a stop. With all this biased context established, I now hereby offer a checklist for those of you aiming to do more of what you love. Pair this with Tara McMullen's fantastic post making the Content Math Work and an eye roll from anyone over 40 saying, I could have told you all this before you wiped out your savings when I was working on free time. The opening epigraph to Chapter eight is a quote from Lao Tzu who says, those who flow as life flows know they need no other force. And when my dad was doing a round of edits on the book, he wrote an asterisk in the margin and he said but one must do some flowing where there is an income stream.

We'll be right back just after this.

Hi, this is Deechen Lackman and I am here to tell you Toyotathon is on. So stop by your local Toyota dealer for incredible year end deals on the cars, trucks and SUVs known for their legendary reliability like the stylish and efficient Camry, the Ready for anything RAV4 or check out a rough and rugged Tacoma or Tundra, all with great fun financing and lease options available to qualified customers. Visit buyatoyota.com to find out more Toyota. Let's go Places.

Close your eyes, exhale. Feel your body relax and let go of whatever you're carrying today. Well, I'm letting go of the worry that I wouldn't get my new contacts in time for this class. I got them delivered free from 1-800-contacts. Oh my gosh, they're so fast. And breathe. Oh sorry. I almost couldn't breathe when I saw the discount they gave me on my first order. Oh sorry. Namaste.

Visit 1-800-contacts.com today to save on your first order.

1-800-Contacts.

All right, so here's the list. Do what you love and the money will follow if you meet more than three of the following criteria. Number one. The economy is booming. Actually booming. Not soft landing or immaculate disinflation booming. Number two. You're clear on what you love in the first place. You're not still in the tinker dabble doodle. Try phase three. You love teaching other people how to teach other people how to make money online.

4. You have enough money in long term investments, index funds and the like to live off the interest alone, keeping the principal tucked safely aside for retirement. 5. You are already independently wealthy. 4. Trustafarian. 6. You have a spouse and said spouse earns a robust living with solid health insurance and a thick paycheck every two weeks. Number seven. You have abundant financial Runway and you don't mind that Runway crumbling beneath your wheels as you try to get the 747 of your passion airborne. 8. Your passion happens to be highly lucrative and or. Number nine. What you love aligns with an in demand, profitable, thriving industry that is not crypto or the arts. The income streams by what you love have not been dammed, dried up or redirected. 10. Even better, what you love includes working a full time job in one of those thriving industries you love leading teams of AI software engineers, for example. 11. You excel at withstanding intense, unrelenting uncertainty and financial pressure. You are also patient and stubborn.

12. You love your passion more than paying your bills on time. 13. You are a dynamo in this now global economy. You possess a one in a million edge in terms of raw talent. Good looks are a plus.

14. You absolutely love sales and marketing, L O V E love. It's a fun game. You never tire of it and you thrive on the competitive art of climbing charts. If a leaderboard exists, you are on it in both senses of the phrase. 15. You have abundant Runway and or a large existing stream of income and or investor funding that funnels enough paid advertising into your passion to achieve profitability. Escape velocity. 16. You're incredibly well networked by birth, fancy parents, schooling, et cetera and or because you love connecting people, you will happily meet with hordes of new industry peers until your passion plane takes flight. I linked to an Instagram reel but does not apply to you. 17. Caveat to number 16 you must be likable and ideally helpful to others too. Just meeting with people won't cut it if they can't stand you.

18. You're porting over a large existing platform, email and or any of the socials to your new passion. Your personal brand plane is already well in flight so that when you punch some buttons on the dashboard to alter your course, you can now land wherever you want. See also Celebrity book clubs by the way, those Reese boxes make great gifts. 19. What you love is also in the highest good. It's aligned with your soul path, what the world needs and or what the market wants. 20. You've hit a stroke of great luck in perfect timing for pursuing what you love and the money following. See also Success and Good Fortune and the Myth of Meritocracy by Robert Frank. What did I miss in this list? I would love to hear from you in the comments. In conclusion, ten years ago I read Steve Martin's biography Born Standing Up. I was inspired to read it by Cal Newportz for so good they can't ignore you entire treaties. Building upon one of Martin's most famous pieces of advice, Martin recounts this idea in a 2007 interview with Charlie Rose. Here's a one minute clip for context.

Someone stood up in an audience somewhere and said to you, how do you be successful? And you said, you have to be undeniably good at something. Well, it really is this. When people ask me say, how do you. How do you make it in show business? Or whatever. And what I always tell them, I've said it many years and nobody ever takes note of it because it's not the answer they wanted to hear. What they want to hear is here's how you get an agent, here's how you write a script, here's how you do this, here's it. But I always say be so good they can't ignore you.

And I just think that if somebody's thinking, how can I be really good? People are going to come to you.

It's much easier than doing it that way than going to cocktail parties.

Cal's book does a better job than I can dispelling Pursue youe Passion myths. Primarily, he suggests adopting a craftsperson mindset instead of while building career capital. But still, sometimes despite your best efforts, you simply aren't good enough at your chosen work, love, passion, income. Or you're not good enough in time. Or you're good not great while attempting to thread the needle of a winner take all industry that's also experiencing a significant rise in big conglomerate competition and consolidation.

Like podcasting. So you pivot and you right size your goals and you regroup. You connect with a new crew in the meantime, the ones who are at least happy to hear about all your perils and pitfalls along the way. Just as long as you keep getting back up. You know in your heart something no one can ever take away from you, that at least once in your life you lived fully, creatively, blissfully from the center of what lights you up. You recall those days so fondly, it's as if they were all a dream.

If you enjoyed this essay, I encourage you to subscribe to rolling in doh. If you're not already, visit rolling in doe. That's-o h.substack.com that's rolling in doe doh.

You can also check out my profile to see everything that I'm up to@substack.com ennyblake thank you so much for listening. I hope you have a beautiful rest of your day. And here's to all of our dreams, even the most challenging ones.

If you've listened this far, you get a gold star.

Thank you.

Word of mouth is the most joyful way we can grow this show, and it helps us land interviews with the luminaries and insightful guests that you would most love to hear from. Please send this episode to a friend who might find it helpful, and for show notes and related links from this episode, visit itsfreetime.com while you're there, make sure you're subscribed to the Time well Spent newsletter. You'll get instant access to my Tech Toolkit, a continually updated list of all the software I use, along with the total monthly spend to run my business where no one works full time, even me. Visit itsfreetime.com join remember, you are running the show. It's time for radical reimagining and everything is up for grabs. Let it be easy, let it be fun, and build with love.

The Uniswap Wallet makes crypto easier and safer to own and use, discover new tokens, research confidently, swap instantly, and manage it all securely in one place. The Uniswap Trading Protocol has powered over $3 trillion in volume, and it's trusted by millions worldwide. Buy your first crypto assets in a few taps and experience the freedom of decentralized finance with Uniswap. Tap the banner to get started.