Your pipeline struggles (that might be something else entirely)
I sat down to write a practical guide about managing dry pipelines because I'm hearing from many of my clients that this is what they're facing right now. It's a completely different market. I even developed a system to identify where your pipeline might be leaking. But as I wrote, I kept hitting a wall and thought I was honestly just lacking creative juices.
Then I went to an event with Kat John where we did a meditation and journaling exercise reflecting with our end-of-life self. Kat spoke about the book The Top Five Regrets of the Dying by Bronnie Ware, and my mind detoured to how these life principles intersect as a business owner - particularly for expert-led practices.
Honoring these principles and values is a key step before doing an analytical review of your processes and marketing. Because when you're running an expert-led practice and putting your IP into the world, you're essentially signing up for the deepest form of self-therapy, growth, and internal challenges humanly possible. You can't do this work without butting up against the big questions of WHY. Without facing inner wounds of rejection. Without assessing your self-worth. Without looking at the root cause of your money mindset.
Here's where I landed with how the five regrets show up in expert-led practices.
“I wish I'd had the courage to live a life true to myself”
Working with clients you don't actually love because you're afraid to say no. Hiding what makes you unique or different in your marketing because you think you need to sound like everyone else. Underpricing your work because you don't trust that your unique approach is valuable enough. Or over-delivering because deep down, you're just not sure your thing is good enough as it is.
If your presence and messaging aren't authentic, people can feel it. They sense the compromise - and I'm sure you do too.
So here's a permission slip if you need it: you can design your practice around your working style and preferences. Your offers can reflect your values. You can sell your uniqueness instead of hiding it.
“I wish I hadn't worked so hard”
Many business owners get excited about sales and run with the dopamine (of course I'm included in that statement). Or perhaps you've grown up with messaging that rest equals laziness and productivity is the ultimate achievement. But when you're drowning in delivery, working nights and weekends, wondering why you built a business that owns you instead of serves you - something has to shift.
This is a key decision point. Where you decide to bring on a VA or manager. And if you already have one, checking in to ensure you're fully embodying what it means to accept help - and what that looks like for you.
Because if you can't take holidays of 2-4 weeks at a time, multiple times a year, then I challenge you to reflect on why you're not back in a job.
“I wish I'd had the courage to express my feelings”
In business, this is about having the hard conversations. When a client's scope has crept so far that you're doing triple the work for the same fee - and you haven't said anything. When boundaries get crossed and you stay silent because you don't want to rock the boat. When something goes astray in a project and you just absorb it instead of addressing it.
These unexpressed feelings don't disappear. They build into resentment, burnout, and eventually a dry pipeline because you're too exhausted to do anything about it.
A note for those with business managers: this applies to your relationship with them too. Be honest about what's really going on. Don't protect them from the hard stuff. Actually let them support you instead of managing their perception of you.
The conversation you're avoiding? It probably won't end the relationship. Staying silent might.
“I wish I'd stayed in touch with my friends”
A community of like-minded humans who get your work, your life, your business, and you - that's not a nice-to-have. It's critical. And these relationships need nourishment and intention. They don't maintain themselves while you're head-down in delivery mode.
When the pipeline dries up and you look around for support, for collaboration, for someone to remind you why your work matters - if you haven't tended those relationships, you're starting from scratch. And you're coming from a place of depletion.
Send the message. Comment on the post. Reply to the blog. Remind your friends that their work matters. Not as a networking tactic, but because isolation is expensive and you don't have to do this alone.
“I wish I'd let myself be happier”
This one might be the quietest, but it's everywhere. You hit a revenue goal and immediately raise the bar. Land a dream client and instantly start worrying about the next one. Launch a program and never pause to acknowledge what worked before moving on to the next thing.
The pipeline suffers because you're running on fumes, chasing a finish line that keeps moving. You're so busy trying to get somewhere that you can't see you're already there.
You can pause between wins. You can celebrate what's working without feeling like you're getting complacent. Being present with your success isn't the same as settling - it's the thing that gives you the energy to keep going.
So what I'm wondering is: where are you compromising that you don't have to?
Which of these regrets is showing up in your business right now? Not someday, not in theory - but today, in the decisions you're making or avoiding?
Because the pipeline issues, the revenue dips, the feeling of being stuck - they're symptoms of deeper compromises. The ones that feel small in the moment but compound over time.
You already know what's true for you. You already know what your innate path looks like. The question is whether you'll give yourself permission to actually walk it.
See you online soon,
Katee.
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