The seven-year itch floats the idea that our relationships begin to feel restless after a period of 7 years. We feel dissatisfied. Distracted. Everything feels… routine. I've been wondering if this restless angst also translates to life outside of relationships. Because it's exactly how I feel at this stage of running my business.

Last week was the 7 year anniversary of soft-launching With Jack. Usually I mark the milestone with a celebration—a dinner in a nice restaurant or treating myself to something I've had my eye on. But for the first time ever I had forgotten the anniversary. It wasn't until Facebook notified me that I had a memory to look back on that I remembered what this date represents.

The Facebook memory is a photo of me in Berlin. I'm smiling because I'd just launched the business I'd spent years trying to get off the ground. When I look at this photo I don't just see a hopeful Ashley, excited about the challenges and possibilities that lie ahead. I can smell the photo. I can taste the photo (it tastes like grapefruit Schofferhofer). I remember exactly how everything felt in that moment.

Fast forward to 2023. We currently have a jaded Ashley who feels underwhelmed with her progress. She feels like building a business in a heavily regulated industry is stifling her ability to be creative, to experiment and to grow With Jack into the beast she knows she's capable of building.

If I could rewind to 2016 I would warn myself that—7 years on—I'd still be manually processing everything. I'd watch countless competitors launch, most of which are VC-backed, and steamroll ahead with traction. I'd develop an unhealthy relationship with my computer because of the notion I always have to make myself available, desperately playing catch up because of my technological disadvantage. And because of this I'd struggle to grow With Jack and would wrestle with feelings of burnout.

Maybe I'd make a different choice. Or maybe not. The insurance industry and I have a lot of history and it's always felt like we have unfinished business. It's probable that most paths would have lead me to this point.

These feelings have intensified in the past 6 months. They're not going anywhere so it's important I work through them (even writing this blog post has felt therapeutic). This is where I've got to:

  • The insurance industry is always going to be difficult to build a business in. That is not unique to me
  • There's no point in expending energy on the things I have no control over. The process of automating my business is arduous. We're 4 years into it. I'm tired and frustrated. It gets me down. Instead I should focus on the things I do have agency over
  • I can give into the seven-year itch and be distracted by something new and exciting, but that too will inevitably lose its sparkle. Why not lean into this and see it through? Maybe there's something magical on the other side
  • I want to build software. Writing code and building something tangible would feel like a creative outlet. Similar to the SaaS I built for a previous business, the product wouldn't detract from With Jack—it would add value. The thought of this excites me
  • For every customer that complains I'm not quick enough to send them their quote, there's a customer that thanks me for the personal touch. You can not please everyone so stop wasting energy trying to
  • I am lucky. A couple of thousand freelancers have put their faith in With Jack. It might not be the 10,000 I'm striving for and it might not be the 20,000 others have, but it's something. I must keep going!

There's a really good book I read called Grit. This book says the secret to outstanding achievement is both passion and perseverance. I might not be feeling at my most fiery right now, but I have grit. I have endurance. Let's see where it takes me.

The day I launched my business in Berlin