Failing My Way to the Top
Edition #90 of Earn After Reading
There’s something I need you to stop being terrified of.
And no, I’m not going to say unidentified males in dark parking garages, MSG, irrational fears of being chased (guilty), or aliens attacking Earth in the near future.
Maybe you should be afraid of those things…
I’m talking about failure.
A miss.
A flop.
A fumble.
A cringe.
A bust.
A train wreck.
An oops.
A dumpster fire.
A ‘went down in flames’ moment.
Whatever you call it… I need you to stop paralyzing your actions because you’re scared to fail.
Quite frankly, this is what’s keeping you mediocre.
And I’m not just talking about the fear of failing in business.
You’re afraid to fail at your commitments (personally and professionally), so you just don’t start them at all.
You’re afraid to leave the job you hate because ‘what if’ the side gig you’re trying to make legit is a flop.
You’re afraid to leave your unfulfilling boyfriend or girlfriend because you don’t want to start all over in the relationship department and consider the time spent a ‘waste.’
You’re afraid to start posting online about the things that excite you because you don’t want the first couple of posts to be a bust.
Every single person around you (me included) is living their life making decisions based on fear.
You, me, and everyone else are deciding what to do and what not to do all because of the negative ‘what if’ scenarios that pull us back from taking risks with great rewards.
Trust me, I’m all too familiar.
And if you don’t believe me, let me just paint a picture of the wonderful failures I’ve endured in my 29 years on earth.
(I did not go to bed last night with the intent to expose myself on the internet with every last fuck up under my belt, but here we are…)
FAILURE #1
In 7th grade, I made the cheer team at the brand-new middle school I had just moved to. I didn’t know anyone, but I nailed those tryouts.
Just a month before the official school sports season started, I got caught on MySpace saying some bad things on a public post (that I absolutely will not repeat here, but my mother who’s reading this knows exactly what I said). 🫠
Not only did someone on my team rat me out (she would’ve never made it alive in the mob), I got benched from cheering for the first 5 games of the season and had to explain to everyone in 7th grade why.
And for those who didn’t play sports–when you’re benched, you still have to show up to the game in full uniform but sit out on the bench like an exposed thumb the entire time.
Embarrassing isn’t even the word.
FAILURE #2
To keep this one short and sweet, I got divorced (and shunned) by my church at age 21. The big ‘D’ Scarlett letter was branded onto my reputation before I had ever even lived on my own.
In hindsight, the divorce itself was the best decision I ever made in life. Regardless though, I’m another bead in the 50% statistic bucket of divorce rates in the U.S.
(I guess that’s good news for you because if it’s 1 in 2, I already did the deed… I guess that counts you as safe. 😜)
FAILURE #3
Pretty much the entire year after my divorce was a giant dumpster fire that I probably will never tell most people half of.
At the time, I was enrolled in art school at the University of Houston. I had spent years building my body of work as a film photographer and multi-media artist.
I was accepted for a transfer to the School of Visual Art and Design in Manhattan (my absolute dream) and had paid my first round of dues and registration to begin in the fall of 2017.
I ended up not going because I was anxious to move there with my husband at the time, knowing divorce was what I really wanted. If the divorce went down in NYC instead of at home (in Houston), I didn’t know how I’d be able to live in Manhattan and pay for school on my own.
(There’s a version of me out there in an alternative universe who moved to NYC in her 20s and experienced life as a young artist in the city 🥲)
After the divorce, I decided to finish my bachelor’s degree at the University of Houston’s Fine Art Program, with a major in film photography/digital media and a minor in art history.
I only had 1 year left to complete to earn my degree–I just needed to be accepted into the strenuous photography program which was a full load of high-level disciplines in the arts.
The spring after my divorce was my final semester, where I would present my portfolio through a difficult critique process to be accepted into the program by my professors.
This was also about the same time I began working at the strip club and bartending at multiple different spots across the city. As you can imagine with that kind of lifestyle, I started ditching classes because I partied too late the night before or worked a shift until 4am.
My inspiration and creativity were at an all-time low to make art.
I was simply surviving, numbing myself to pretty much everything around me.
Can you guess where this story goes?
I didn’t get into the program.
In the words of my professor, “You don’t seem like you’re committed” which also proceeded with her recommendations that I should see the campus counselors to get some support because something “changed” in me since I started taking her classes.
Uh, yes, ma’am. Divorce and religious trauma will do that to you. Oh, and don’t forget about good ole’ depression!!!
I was devastated. Beyooooond devastated.
Since the moment I picked up a DSLR camera at 14, this was everything I wanted to do with my life.
Every dream/idea/conception of what my career would look like tanked, along with every ounce of confidence and belief in myself I had left.
Which leads us to…
FAILURE #4
Since I didn’t make the program, my options were to 1) switch majors or 2) take a fall semester of art classes and try again to get accepted into the program the next year.
I said, “fuck it” and dropped out entirely mid-semester.
For some, dropping out might not sound like a huge deal to you.
For me? I was a straight-A student my entire life, top 3% of my class, teacher’s pet out the ass.
Getting a college education was an identity I placed on myself probably in kindergarten.
My failing school deserved the death penalty in my mind.
I was more embarrassed about dropping out of college than I was explaining to guys on dates that I was a 21-year-old divorcé 😬
And to speed roll through a few more moments in my failure gallery:
#5 I got knocked up by a guy I had only been dating for 2 months (thank god it worked out because we’re here 7 years later, happily married) but that was just the icing on the cake of the shit show I was living through.
#6 I have launched multiple offers/courses/memberships in my business that have TOTALLY flopped. We’re talking please-delete-every-record-that-this-thing-ever-existed-because-it-sucked.
#7 I took an (unintentional) YEAR off my podcast because I was too overwhelmed/burned out/ didn’t prioritize it, even though it was really important to me. (Thankfully, we’ve recovered from that one too.)
#8 Last year, I got a job that I thought was literally written in the stars for me. I quit said job a few months later and had to explain to, what felt like, hundreds and hundreds of people why I quit. (Maybe not quite a ‘failure,’ but it still felt like one.)
#9 Just WEEKS after quitting that job, I got into a bad business deal/partnership with someone I barely knew (ok, this one was just downright dumb because red flag after red flag was planted in the sand like a gas company working on an underground line.)
WARNING. DANGER. AVOID AT ALL COSTS.
I didn’t listen to my gut, or my husband, or pay attention to a single flag (you’d think I was color blind), and instead chose to completely intertwine my life with said ‘business partner.’
I eventually came to my senses and realized this was NOT for me, and got myself out. Again having to explain to the masses what happened to that ‘cute new Pilates studio’ I was opening.
Should I keep going, or do you get the picture? 🙃
Fuck-ups are inevitable.
But is your fear of fucking up holding you back?
What if we, just for a second, painted all the ‘what ifs’ in a different light?
What if you finally committed to starting that new sport, even though you think you’re ‘out of shape,’ and it completely changed your life and gave you a new sense of confidence and community?
What if you finally did leave your shitty job to take your side-hustle full-time and it becomes wildly successful and gives you the time/financial freedom to live your life on YOUR terms?
What if you ended the unhealthy relationship that has been dragging on for far too long, so you could finally start working on yourself and find a relationship that’s really meant for you?
What if you actually post that idea online and it goes viral?
Things start to look a little different when you start weighing the risk vs reward–you begin to realize you don’t have to be paralyzed by fear, but instead, you can feel inspired to take action.
And even if you DO fail, are failures really all that bad?
Or are they the solid foundation on which you can rebuild your life (as JK Rowling has famously said)?
You have to fail to learn how to rise.
And baby, we are rising.
Show yourself some love today.
You’ve earned it.
As always,
Taylor
Hey, I’m Taylor Hedden—business consultant, podcast host, and the voice behind some of your favorite content (even if you didn’t know it yet). When I’m not building better business experiences or dodging burnout like it’s my full-time job, I’m writing here to keep things real (and occasionally roast the internet).
Keep creeping (with intention):
✦ Find me on Instagram @tay.hedden & @chanelandlee for the unfiltered side of business, motherhood, and making it work.
✦ Listen to Ironically Serious—my podcast where I unravel life's wins and mess-ups, one unhinged episode at a time. It's like therapy but with more laughter and less couch.
✦ Need help fixing the stuff in your business you’ve been side-eyeing for months? Head to chanelandlee.com for real strategy that doesn’t waste your time.
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