Death of a Workaholic

The Messy Middle ft. Jenny Lynne

Jenny Lynne Season 2 Episode 1

“Here lies Jenny. She just had to send one more email.”


Change is never clean and tidy – it's a swirling, gooey, messy adventure.

I prided myself in my work ethic for my entire life and felt like that was the only option out there, but boy did I have a tough time when my kids’ dad was diagnosed with cancer.

I was confused, lost, and just mentally exhausted. How was I going to take on both roles? How was I going to be mentally present with my kids while running a business?

After I hiked the Camino in Spain I found my answers. I went from “I don't know where I'm going" to "I know exactly where I need to be.”



Key Takeaways

  • Embrace the mess. Grab hold of the reins knowing it will be a bumpy and sticky ride. Change can be both torturous and filled with possibilities.
  • Don’t wait til you’re on empty to refill the gas tank. You’ll find that the power of self-renewal and fostering meaningful relationships feeds your soul.


Key Moments

{2:07} “I was a proud expert at doing the next thing on my list instead of the best thing in my life, and I had no desire to change that for 20 years. It was working for me in so many ways.”


{5:00} “I realized that over this whole period, other than the occasional favor I called in, I sucked at asking for and accepting help.”


{10:49} “If we are going to be that best person, if we are gonna love in the best way possible, if we are gonna parent in the best way possible, if we are gonna work with our best ideas, if we are gonna lean into life, then we have to take that armor off and we have to embrace the mess.



Get in touch with Me

jenny@hellojennylynne.com



Share your Story

Send it to us at podcast@jennylynnerickson.com



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Jenny Lynne: Every story needs an inciting event. Something that sends us on a different course than where we came from. And our relationship with work is no different. We either get pushed off a cliff with no choice but to change, or we get pushed into a position where we realize that we want to change. Or if we're lucky, we get pulled towards something that is better than what we have now.

But that's not always that easy either because we human beings don't like change so much. So we tend to dig our heels in a little bit. Regardless. It's messy. Change is always messy. Sometimes the mess is torturous, and sometimes it's like an ambiguous goo that your feet are caught in. And sometimes, uh, it's like a sense of [00:01:00] possibility.

That's rooting us back into the ground. A hope for what could be. But the more people I talk to, the more I realize that they've rarely strung together the chronologies of their middle. What is the timeline? What were the real turning points in their journey? What are the signs that we missed before we got the kick in the pants?

And how do you move from, I don't know where I'm going, but I know this ain't it, to. I know exactly where I need to be right now. Season two is all about finding the answers to these questions. And my middle was messy. I had no desire to change. For the longest time, my off switch for work was located on the top floor of my mind, accessible only through a steep spiral staircase and a super secret tower filled with cobwebs that you could only open the door when the planets aligned and the skeleton [00:02:00] key caught the full moon at the stroke of midnight.

In other words, I kept that thing locked up and I threw away the key. I was a proud expert at doing the next thing on my list instead of the best thing in my life, and I had no desire to change that for 20 years. It was working for me in so many ways. The emails that I pounded out feverishly at 2:00 AM got me accolades for what I was willing to do to make sure things were successful because, you know, people really read those things at 2:00 AM right.

And the to-do list that ran through my hut when it hit the pillow was what allowed me to stay ahead of the curve and everybody else. I had built an income, a network, reputation, accolades, and security, all by burning the candle at both ends on the regular, with occasional seasons of rest in between to repair.

I defined success as loving what I do, making an impact, having meaning, and being challenged every day while I [00:03:00] made a good living. And so in order to make sure that kept happening, I changed jobs regularly because, you know, I keeps things spicy, right? But it really showed up and a joke with my kids about the epitaph that would one day be on my tombstone.

Here lies Jenny. She just had to send one more email. I'm pretty sure you can relate to that one, but that joke became a wake up call when the news about the cancer came through Stage four and 5% chance of making it to five years is nothing to sneeze at. The kid's dad was scared for himself and I was scared for us.

For the first time I wanted to find my off switch for work. No, that's a lie. I needed to find it. And so for the next few weeks I. I ensued a pruning fest. I got [00:04:00] rid of everything that didn't generate revenue while I processed what was happening in my life. It gave me a sense of control when I had absolutely none and when the kids needed me, I dropped everything for the first time in my life, embarrassingly to admit I was a mom first.

And a worker second. And when the situation started to decline, I made more changes. I hired an assistant. I started thinking about succession planning and figuring out if I would be okay if I had to step away from work for who knows how long. It wasn't until I went to Spain to walk the Camino that I actually figured it out.

It was eight months after the diagnosis, and it was a last ditch effort for me to spend some me time before I knew it would be 100% on my shoulders. Let me repeat that. I believed it would be all on me, [00:05:00] and I realized that over this whole period, other than the occasional favor I called in, I sucked. At asking for and accepting help.

I had learned to delegate, but all the roads still led to me and in life. I hadn't really asked for any help at all. I cried after every single day, hiking a dozen miles on the Camino, not from physical exhaustion, although I will admit everything hurt, but from an empty gas tank that I had truly not refilled in years.

It was mental exhaustion. Emotional exhaustion, and I hadn't really fostered the kind of relationships that I needed in order to feel comfortable leaning in. I mean, I, I'd been giving and kind and done all the stuff right, but, but that's not enough. It's not what it's about. It's about trust, and I was missing it.

I ended my trip on the shores of [00:06:00] Feister. Now Feister is the end of the road for pilgrims who've hiked the 500 miles on the Camino. It's a beach, and they came there to strip their clothes, burn them, and jump into the water as a final act of cleansing back when that was kosher, which it's not really anymore.

I had just finished my own rimage and I was standing there naked with my clothes on. And a song came to me. I don't remember all the words, but I do remember the feeling.

I sang a song with words I'll never remember.

A moment I never forget

the wind.[00:07:00] 

Hi, said goodbye.

I said goodbye,

and it was more than just saying goodbye to Dave. It was about saying goodbye to all of the experiences that had woven themselves into the clothing. The clothing then had protected me. Covered me and comforted me over the years because those experiences may have shaped me, but they were not the right ones to guide me in the life that was waiting for me back home.

It wasn't what the kids needed. It most definitely wasn't what their dad needed, and it was not helping my bank account in the least, but I thought it was me at my core. [00:08:00] In reality, it was just an outfit that I had gotten really freaking comfortable in, and I did not know who I was underneath all that. So I sat on that shore where the pilgrims used to skinny dip and burn their clothes, and I started to undress the identity most holding me back, my workaholic.

It felt a lot like a favorite comfy tea. You know, the one in your closet that you just can't seem to get rid of it. It's got holes in it and it doesn't fit you anymore. But man, this is so gosh darn comfortable. And mine was covered in stripes and each stripe represented a voice. A voice from my past reinforcing how hard work was the only reason.

That I had made it this far. Now, hard work is absolutely important, but it is not the only reason. So why had I encoded that message? Just like I would not dream of wearing that [00:09:00] t-shirt into a board meeting, and I wouldn't dream of wearing a suit. Well, at least a Brooks Brothers suit onto a ski slope. But at some point I stopped taking the T-shirt off.

I just wore it everywhere. And that identity, that t-shirt, it helped me build a solid life, but it, it is not, and was not the right identity to break through the ceiling that I had created for myself. And I am guessing you have a few ceilings that you've created for yourself too. That was the day I released my voices.

The day I took the t-shirt off is the day I started moving forward, and for the next year, I stripped down my armor in what Brene Brown calls a brutal midlife unraveling, and I started to rebuild it. Now my workaholic is dead and gone, but I will be fully frank. I am still rebuilding and tearing down portions of my identity.

And I have talked to a [00:10:00] lot of people over the last six months. Um, many of them will say that it's a year to 18 months for this period of realizing what it is that they have to change, and then another five to six years of exploring to actually make those shifts. So I'm in for the long haul. This was my messy middle.

I had been a turbocharged hamster running on a wheel for so long, moving faster and faster, but not really going anywhere. And the sad part is I didn't see it clearly enough to realize it. I didn't step off the wheel. I got full long off, but at least I got off. Our best selves are underneath the armor that we've set up, the armor that we've built.

So if we are going to be that best person, if we are gonna love in the best way possible, if we are gonna parent in the best way possible, if we are gonna work with our best ideas, if we are gonna [00:11:00] lean into life, then we have to take that armor off and we have to embrace the mess. So come with me into season two.

It's time to explore the messy middle.