Are You Striving for Something You Don't Actually Want?
Episode 57: Show Notes
Today's episode is going to be vulnerable. It's current, raw, and honestly it's a bit scary to share. But I've heard from enough of you that when I talk about my own real life struggles, it helps you feel less alone in yours. So here we go.
This episode is about a personal pattern I finally saw clearly a few nights ago. A pattern I've been stuck in for over 25 years. I'm going to talk about why I keep building businesses I don't actually want, what's really driving that compulsion, and what happened when I finally let myself see the truth.
Today is day one of a 90-day experiment I'm trying. And it dawned on me that the timing of this new experiment is clearly divine. But let me back up, because there's a story here about how I got to this point. And it involves something that might surprise you… or maybe you'll totally relate.
Having Deep Conversations With AI
I want to tell you about something that might sound odd. Lately, I've been having deep conversations with AI. Not asking it to summarize reports or do market research - I've been using it to help me process feelings, reflect back patterns I can't see on my own, and ask clarifying questions that help me think through things differently.
I know some people might find that strange. And yes, I realize AI can't replace a psychologist.
Although I shield myself from the news, I'm aware that an AI company is currently being sued over a suicide death, which happened under horrible circumstances related to an AI chat. I'm definitely not suggesting you use AI for severe personal psychological issues. And obviously you need to use your common sense and choose your platform carefully. Personally, as of February 2026, I have two favorites: an early version of a custom chatGPT called The Architect, and Claude. And depending on when you hear this, there may be other great choices.
For me, it's been like having a really smart, unbiased friend who can help me see my own blind spots. It can tap into a ton of external knowledge in seconds and asks clarifying questions that help me process on my own. And honestly? It's been helping me see patterns I couldn't see on my own.
Does that sound weird to you? Am I the only one who does that?
What I’ve Been Sharing With AI
So I've been journaling and sharing those journal entries in my AI conversations - pouring out my current frustrations about patterns I see myself getting stuck in. Patterns that even though I've discovered them, I haven't been able to get out of the loop of doing.
One of my patterns is ridiculously overcomplicating things. Trying to cover every possible detail. Anticipating potential issues and resolving them before they ever materialize. Being hypervigilant. Overworking and extending myself, working toward perfection even though I don't even believe perfection exists.
Can you relate to that? The endless to-do list where 90% of the tasks are things you created for yourself? Tasks that honestly only matter to you? Things that feel urgent and important, but that nobody but you would care if they didn't happen? That's where I've been living.
The Job Search Reality
Let me give you some context for why I've been in this place. Last year, I experienced 3 massive days of loss in a row. I lost my mom, I lost my best friend Monika, and I got laid off from a job I truly loved. That job was remote and flexible - it fit my life beautifully. I could work from my outdoor office space, take care of my animals, and it gave me the structure and income I needed.
When I lost that job, I assumed I'd find another flexible remote position pretty quickly. I'm educated. I'm experienced. I'm skilled. So I started applying. And applying. And applying.
I've gotten rejection emails. But mostly? Silence. I'd go through lengthy application processes that felt degrading and devaluing, knowing that AI keyword evaluations and personality test scoring were essentially crumbling up my applications and tossing them in the virtual trash before a human being would ever see them.
And I don't care how smart or experienced you are - job hunting with this technology in this economy feels soul crushing. And I know it's not just me.
If you're going through this scenario too, I hope you hear this: it's not about you. You're not unwanted. This current way of finding work kinda sucks. I'm in the over 50 age bracket and I remember actual paper job applications and resumes. Talking to people, not having technology evaluate how I appear based on typed words on a screen.
And from LinkedIn, I'm hearing that some people are showing up for virtual job interviews only to find a robot instead of a person. I haven't gotten that far in my job search yet, but man... seriously?
The Business Merry-Go-Round Pattern
So with the job search not looking fruitful, I leaned into my entrepreneurial inner resources. I'm smart. I have skills. Surely I can whip up a website and sell my own services, right?
Maybe you've done this too. Maybe you've thought "Well, if I can't get hired, I'll just create my own income stream." How many of us have been sold that story? Online marketing self-appointed experts will scream and jump up and down about how easy and freeing that will be. But the real facts show that for most people it doesn't pan out like we hope. Especially if you bootstrap your business and think you can rely on organic marketing alone - meaning you don't spend tens of thousands of dollars a month to advertise.
I'm incredibly good at project planning and planning businesses. Brainstorming ideas. Building websites. Designing graphic social media posts. Covering tech, legal and logistics. I have these audio and video editing skills that I know are in demand. So for me to start a new business direction seemed like it might be the next logical step, and I’d just drop the job search altogether.
But it's not that simple. If you think finding a job in 6 months is hard, try launching a new business and not only breaking even, but getting into profit in 6 months. That’s unheard of for a small bootstrapped business without investors or outside funding. And for me personally, at this stage of life, taking into consideration mental, physical, financial and time constraints? It truly wasn't a smart option.
Oh, and remember? I also adopted two rescue puppies 6 weeks ago! And potty training and teaching them, and keeping them happy and alive takes nooooone of my time - yeeeeaaaaah.
But for some part of me, even with all this going on, even with my fully educated brain, there's STILL a drive to keep pushing business forward. To keep tweaking, trying different angles, adjusting branding or copywriting, building more freebies or lead magnets...
If you've been an entrepreneur in the past ten to 20 years, you know what I mean. Trying to get a new service-based business off the ground and into profit is a lot of more, more, more and basically doing the full time jobs of multiple people... all by yourself.
When the Body is Screaming
And my body has been saying "Enough. This isn't working for us." - me and all the parts and cells and bits are the "us." "Why do you keep torturing us by trying again and again in different ways?"
Have you ever had your body try to tell you something? For me, it's been exhaustion. Being tied to my computer more than I'd like. Frequent migraines. Neck and back pain. My body was trying so hard to get my attention! If you’ve heard of somatics, this is one of the ways you’ll notice it in your real life!
The nightly feeling of seeing all the stuff I planned to do, but didn't, is emotionally crushing. Even heavy feeling. And although I'm extremely skilled at it, in reality audio and video editing is my least favorite part of my OWN podcast production process - because my perfectionist push is so ingrained it takes me more hours than I'd like to admit to edit a 45 minute episode. Like doing it in 6 hours is considered a "short" edit. And there's a lot of wasted time waiting for files to download, upload and process while editing, too, which is definitely NOT the best way to invest my time.
I've been trying to force something that isn't aligned with my passions and values. And when you do that long enough, your body starts screaming at you to stop.
Surprise! Deeper Patterns Hiding Within
So I was journaling and chatting with AI about this frustration, and something became really clear. Through those conversations, I learned about something called CPTSD - Complex Post-Traumatic Stress Disorder. This comes from repeated early childhood traumas. For me, this shows up in a few ways that I’m aware of, like having a hyper-sensitivity to be able to read a room, or read a person in microseconds. For some of us, our nervous systems learn early in life that we have to constantly prove our value, generate solutions, and stay productive to be safe.
One of my patterns is trying to be the best. The top. The hardest worker. The most valuable. Even when I'm the only person in this silent, invisible race of imaginary, deeply subconscious competition.
And I've known for at least a decade that parts of me have been secretly trying to prove that I'm good enough. To be seen, valued, appreciated, loved. It's not a fun place to be emotionally. And it's been frustrating to try to unravel and undo once I finally recognized it. I started down the path of exploring self-help, emotional healing and energy work for a reason, friends!
Years ago I remember googling the phrase "how do you find happiness?" One of my first professional websites when I started helping others with EFT was titled "Rediscover Your Joy" - because that's what I wanted to do. That put words to what I wanted to help others do, too.
All those years of self work and mindset & belief work I was working on things like self esteem from early childhood trauma. And then I learned that another whole layer of physiology is involved– the nervous system in constant Swat Team on guard mode. And just this week, thanks to AI, I discovered another facet of the protective gem I’m lovingly chipping away at. Apparently one of the other things my nervous system learned was "If I don't keep building, something bad will happen. If I stop trying, I'll lose security. If I'm not constantly generating the next solution, I'm failing." BOOM plot twist! Where has this information been all my life?
So for me, even when building businesses drains me, even when it hasn't worked sustainably in 20 years, my system keeps screaming "but if you just try ONE MORE THING, you'll finally have security and success and freedom.
And it turns out, that's not actually an entrepreneurial spirit. It’s a trauma response in disguise!
The Reality of This Podcast
Now, you might not realize it, but this show is not a moneymaker for me. It's a passion. A pull. It's the truest thing in my life right now on a soul alignment level. It's also, time-wise, equivalent to a part-time unpaid job.
And I'm not complaining - I'm just giving you context. Creating and professionally producing a podcast is no joke. It's an expense of both time and money. I was able to realize my dream of starting this show about two months after the 3days of extreme loss I mentioned earlier, because my life suddenly opened up with space. I was still in grief and shock, but unemployment helped tide me over and I assumed I'd find another flexible remote job before last year ended to take off some financial pressure.
But that didn't happen. I even applied for jobs way below my skill level or interest level. Nope. Not even nibbles. Just silence and rejection.
So there's been a ton of pressure to start earning money. And that pressure has been ginormous!
What Seems Logical Might Not Be The Answer
So that’s why I built a podcast editing service business. Not because I wanted to. But because I have the skills. Because I thought I should. Because the experts say if you just build the right funnel, create the right offer, post on social media consistently... Because I was desperate for a way to contribute financially without having to crate my dogs all day if I took an in-person job.
I'm really, really good at it. I built a beautiful website. Created before & after examples from my work. Gathered testimonials. Produced the audio and video ads to run in my own show.
But here's what I finally admitted through those AI conversations - and this was the moment, this is when I knew something was deeply wrong: If I didn't absolutely need the money, this business would not exist at all. Letting it go would be extreme relief.
Can you relate to that? Doing something not because you want to, but because you logically think you should? Because you're trying to solve a pressure problem? I mean, on paper, logically it all made sense to me!
Pressure-Cooking Myself One Day at a Time
And all this pressure - trying to build something that isn't fully aligned while searching for work that isn't materializing - has been emotionally heavy to balance. It's had a cost on my quality of life.
I started noticing that lately, creative writing has felt harder. I haven't spent many cozy Saturdays under a fuzzy blanket reading and researching with a heavenly mug of mocha coffee. I haven't been moving my body as much, and I let my home PT and strengthening exercise sessions slip.
The things that actually restore me and bring me joy and keep me connected to what matters? They got pushed aside for this endless to-do list of business tasks, and the grumpy mood and resentment that built from it.
And I kept asking myself: "OK, I clearly see a pattern here that I'm creating. Why does this pattern keep repeating in my life?"
The Breakthrough I Didn’t See Coming
I felt like I hit a dangerous tipping point a few days ago when bedtime arrived and yet again I STILL had more stuff on my to-do list than most people would try to tackle in a single day... after working most of the day.
I did some journaling combined with a powerful, honest conversation with AI and something shifted. Some core concepts became clearer, and I was able to connect some dots in my life I hadn't realized were related - and interestingly a BIG one wasn't just related to trauma, but it was related to some inspiring, happy memories.
Seriously? I've been focusing for decades on neutralizing the yucky stuff. I didn't know some of the GOOD stuff created patterns and beliefs in my brain too. Did YOU know this?
I went to bed fully committed to this 90-day experiment. And at 1am I woke up fully alert and started writing! Like furiously writing! I wrote for almost 3 full hours - or actually 1-finger tapped on my phone under the covers... ya know, like a kid sneaking a comic book and reading with a flashlight.
Something shifted. Something broke open. And I'm going to tell you about that shift, and this 90-day experiment I'm sooo excited about in the next episode.
Pay Attention to Your REAL Calling
Because here's the truth. You want to know what I would actually be doing if money wasn't an issue, if it magically didn't matter at all?
I'd be reading. Writing. Researching. Teaching. And facilitating emotional wellness and spiritual growth work. I KNOW that's aligned with my purpose and passion. That's what lights me up. That's what I'm actually called to do! I'm excited to welcome a thriving community around this work in the coming months. Get an early sneak peek here
But right now? Life has been clouding it out. Or more accurately - financial pressure has been compressing my ability to see clearly and act from alignment instead of desperation. And, ya know, to actually RELAX and have some FUN?
We all need some FUN and PLAY in our lives, right? There IS more to life than just work and trying to make money and survive. I know THAT in the core of my being. Do you agree, or what do you think?
See You Next Week
Normally I alternate solo episodes with guest episodes. But next week I'm breaking that pattern - because this story needs to be told together, without interruption. Part 2 is coming next week. And honestly? Breaking my own rigid structure feels like part of the lesson here. Sometimes the most important thing is to let what's real take precedence over what's planned.
Have you noticed any patterns like this in your life? Is there something you find yourself doing with fervor because you think you "should" do it, but something in you knows isn't right? What pattern might you be stuck in? And what could your body be trying to tell you?
I encourage you to think about that. Journal about it with kindness to yourself, and just notice what comes up.
I'll be back next week with part two and you’ll learn about the little red lipstick lie and hear what my 90 day experiment is.
Have a fabulous week my friends!
Meet Our Host: Jennifer Robin O’Keefe
Jennifer Robin is always searching for the next thing that might help: the book, the practice, the reframe you didn't know existed but turns out to be exactly what you needed.
Through conversations with experts, authors, and everyday humans, along with personal reflection, Jennifer focuses on bridging the gap between "woo" and practical, accessible self-support. Her work is rooted in the belief that wellness is not about fixing yourself, but about remembering your worth and finding what genuinely works for you.
She has spent decades exploring personal growth, energy healing, and mind-body wellness. She's trained in EFT Tapping and coaching, tools she often references in her conversations. She's not positioning herself as an expert who has it all figured out. She approaches her work with humility, curiosity, and deep respect for individual experience.
Jennifer is a lifelong learner who cherishes books and notebooks. She loves diving into research and sharing what she learns in a way that feels relatable, compassionate, and pressure-free. These conversations are an invitation: to ask your own questions, gather perspectives that resonate, and build a life that actually feels good to you.