When business slows down, it’s easy to start questioning everything. Your offers, your marketing, your skills, your content, and maybe even whether people want what you’re selling anymore. Before you burn it all down and rebuild from scratch, I want to sit down with you, pour you a cup of coffee, and talk you out of the spiral.
I’ve been having this conversation with so many business owners lately. Not only do things feel different, but their marketing isn’t necessarily landing the way it used to. heir bookings are slower and for those of us who have been in business for a while, there can also come a point when the business we’ve built starts to feel a little like a hodgepodge of everything we’ve added over the years.
Some things probably do need to change. But that doesn’t mean everything needs to change. In this episode, I’m talking about how I navigate these seasons, why I think high-level human support matters more than ever when we’re questioning our businesses, and the simple “who, what, when, where, why” exercise I use to figure out what actually needs my attention.
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When Business Is Slow, Everything Can Start to Feel Broken
This has been top of mind for me because I’ve recently had multiple conversations with clients and prospective one-on-one coaching clients who are experiencing some version of this. Business feels slower. Marketing feels different. Things that used to land aren’t necessarily landing in the same way.
The reality is that our businesses have to evolve. We have to keep iterating because our markets change, our customers change, and we change, but there’s another layer to this that I see especially with business owners who have been doing this for a while. I almost think of it as the “seven-year itch” of business ownership.
It doesn’t have to happen at exactly seven years, but somewhere around that five-to-eight-year window, I often see entrepreneurs reach a crossroads. You’ve spent years building your business. You’ve created offers, added services, learned new skills, developed systems, experimented with marketing strategies, served clients, and layered one thing on top of another. Eventually, some of those layers aren’t going to belong anymore.
Your business is evolving because you are evolving. The challenge is figuring out which pieces need to be pruned without deciding that the entire tree needs to come down.
Your Business May Need Pruning, Not Reinvention
There may absolutely be things in your business that aren’t working anymore. Maybe an offer needs to go, your messaging needs to change, or you’re serving a type of client you no longer feel excited to serve. Maybe the way you deliver your work doesn’t fit the life you have today, or maybe you’ve simply outgrown something that once made perfect sense.
I’ve held onto identities and offers longer than they brought me joy, worked well, or even felt like they belonged inside my business. It’s hard to let those things go because we created them. We put our name on them, invested time in them, sold them, and told people, “This is what I do.” Then one day, we have to be willing to look at that thing and say, “Thank you, and I’m done with you.”
There’s a writing phrase for this: “kill your darlings.” Sometimes the thing you love because you created it isn’t the thing you’re supposed to keep carrying.
There’s an important distinction, though, between intentionally pruning something you’ve outgrown and panic-pivoting because you’re in a spiral. When everything feels shaky, I don’t want to accidentally throw away something perfectly good alongside the pieces that genuinely need to go.
Before You Change Everything, Remember Who You Are
One of the first things I think we need when we’re spiraling is another person who can help us sort through the muck. I want someone who can hold up a mirror and remind me who I am, what I’ve accomplished, how far I’ve come, and how much I actually know.
Because when I’m deep in a spiral, it can be incredibly easy to forget her. I forget the woman who figured things out before. I forget the clients I’ve served, the money I’ve made, the problems I’ve solved, the five-star reviews, and all the evidence showing that I actually know what I’m doing.
A temporary downturn can make us question years of evidence. That’s why I think getting outside perspective is so important, particularly from someone who understands you, your work, your customers, and your business. When I’m questioning everything, I don’t necessarily need another strategy thrown at me. Sometimes I need someone who can help me sort through what is actually happening and remind me of what I already know.
Why I’m Careful About Turning to AI for Business Clarity
AI is another part of this conversation because I’m seeing it come up more and more with business owners. I use AI. My clients use AI. These tools can be incredibly helpful for doing some quick math, working through analytics, organizing information, or processing data.
I think there’s a line we need to be very careful about crossing. AI can help me process information, but I don’t want it to become the place where I outsource my knowing.
There’s a huge difference.
If I start asking AI to tell me who my clients are, what I should say, what content I should create, how I should position myself, what my next offer should be, and where my business should go, I can slowly disconnect from my own instincts and expertise. AI only knows what I give it. It doesn’t have the full context of every client conversation I’ve had, it hasn’t watched my business evolve over the years, and it doesn’t know all the nuances behind why I made certain decisions.
More importantly, it can’t adequately reflect back to me all the expertise I’ve accumulated along the way.
I’m seeing business owners become more confused as they use AI more heavily, particularly around content, client confidence, brand positioning, authority, and their sense of who they are. I don’t think that happens because they’re trying to cut corners. Quite the opposite. Most of the business owners I work with genuinely care about doing excellent work and serving people well. They’re trying to use the tools available to them intelligently and save time.
But there’s a difference between using a tool and allowing that tool to become your source of confidence and clarity.
Don’t Outsource Your Conviction
Creating content is a great example of this. When we constantly ask something else to tell us what to say, we can get out of practice using our own voice. It’s almost like a muscle. We stop exercising our ability to notice what our clients are saying, connect those observations to our expertise, form an opinion, and communicate it with conviction.
Then, when we need to create something ourselves, we feel stuck. We’re no longer as practiced at sitting down and asking, “What do I actually think about this? What have I seen? What do my clients need to hear from me?”
That’s why I want to be intentional about what I outsource. I can outsource speed, organization, and some data processing. But I don’t want to outsource my confidence, clarity, understanding of my clients, or knowing of where my brand is going.
Especially when I’m already spiraling and questioning myself, that’s when I think high-level human advisory becomes incredibly valuable.
Be Open-Handed With What No Longer Fits
Once I’ve grounded myself again and remembered where I’ve been, who I am, and where I’m going, I can start looking at the business more objectively. This is where I want to become open-handed, because there may be things that genuinely don’t belong in this next era.
I have absolutely held onto offers and identities longer than I should have. Letting something go can be hard because there’s often so much history attached to it. Maybe it helped build your business. Maybe people know you for it. Maybe it made great money for a long time. None of that means you’re obligated to keep doing it forever.
Growing into the next era of my business requires me to acknowledge that certain offers, services, identities, or ways of working might not fit anymore. But instead of asking, “Should I change my entire business?” I’ve found it much more useful to get specific about what is actually causing the friction.
Should You Pivot Your Business? Start With Who, What, When, Where, and Why
When I’m not loving my business, one of the most helpful exercises I can do is work through five simple questions: who, what, when, where, and why.
Rather than treating dissatisfaction as evidence that the entire business is wrong, I can use these questions to isolate where the friction actually exists. This gives me something much more concrete to work with and helps me distinguish between needing a complete pivot and needing a smaller adjustment.
Who: Do I Still Want to Serve These People?
First, I can look at the who. Do I still enjoy the people I’m serving? Do I feel connected to their needs? Do I understand their problems, and do I still want to continue solving those problems?
Sometimes the work itself is still right, but the audience has changed — or I have. Maybe I’ve developed expertise that allows me to serve a different kind of client now. Maybe I’m finding myself increasingly energized by conversations with one type of person and drained by another.
If the “who” no longer feels right, that gives me much more useful information than simply saying, “I hate my business.” I can begin looking specifically at my ideal client, positioning, messaging, and offers instead of changing everything at once.
What: Do I Still Want to Do This Work?
Next is the what. Do I actually like the work I’m doing? Maybe I love the people I serve, but I’m tired of delivering a particular service. Maybe an offer that once energized me now feels heavy. Maybe I’m doing something because I’ve always done it, not because I still want to.
That could point toward an offer change without requiring a complete business reinvention.
I think this is especially important for established business owners because we can become so identified with what we’ve always done. Other people associate us with it, our websites are built around it, and we have years of proof that we’re good at it. But being good at something doesn’t mean I have to keep doing it forever.
When: Does This Work Fit My Life Anymore?
This was a huge one for me. When I became a mom and began reevaluating my photography business, it wasn’t necessarily that I hated the work. The when had become the problem. Photography required me to be gone at times I didn’t want to be gone. It meant nights and weekends, and it required a schedule that didn’t fit the life I wanted anymore.
That distinction mattered because I didn’t have to decide that everything about the work was wrong. I could identify the actual source of friction: the when.
Our lives change, and it makes sense that our businesses may need to change with them. What worked beautifully in one season of life might feel completely unsustainable in another. That doesn’t make the original business model bad. It simply means I have new information about what I want my life and business to look like now.
Where: Does the Way I Work Still Fit?
For me, the where was closely connected to the when. Where did the work require me to be? Did I want a business that required me to leave home? Did I want more flexibility? Would I feel differently about the work if I could choose when and where I did it?
Those questions opened up possibilities I might have missed if I had simply concluded, “I don’t want this business anymore.”
When I realized I could still do amazing things while gaining more control over the when and the where, I could follow that clue. It helped guide my pivot because I wasn’t trying to escape everything about my existing business. I was moving toward a business model that better supported the life I wanted.
Why: Does My Original Reason Still Mean Something to Me?
Finally, there’s the why, and I think losing sight of our why can make us feel incredibly untethered. We start asking ourselves, “Why am I doing this? Do I even like this anymore? What am I building toward?”
When I don’t know why I’m doing the work, creating content becomes harder. Showing up consistently becomes harder. Sales calls become harder. Serving clients well can even become harder because I’m disconnected from the reason I’m doing any of it in the first place.
Here’s something I want you to know: your why is allowed to change.
The reason you started your business does not have to be the reason you continue building it. You’re different now. Your life might look different. Your family might look different. Your goals might look different. The things you value may have changed.
Maybe your original why was about creativity or telling stories. Maybe that felt deeply meaningful at one point and doesn’t feel as powerful anymore. That doesn’t necessarily mean you need a new business. You might simply need a new why.
Sometimes the pivot isn’t an entirely new offer, audience, or business model. Sometimes the pivot is in your positioning and your connection to the business you already have.
You Don’t Have to Solve the Whole Business at Once
This is why I love the who, what, when, where, why exercise. A business spiral makes everything feel enormous because every thought is flying around at once. My marketing isn’t working. My offer is wrong. My audience has changed. I should pivot. I need a new skill. Maybe I should add what that other person is offering. Maybe nobody wants this. Maybe I’m done.
The five questions slow everything down.
Instead of asking, “What’s wrong with my business?” I can ask something much more specific. Is it the who? The what? The when? The where? Or the why?
Once I know which question is actually creating the friction, I can start making intentional decisions from there. Maybe I need a new offer, but I don’t need a new audience. Maybe I still love my work, but I need to change when I deliver it. Maybe everything operationally works, but I’ve lost touch with why I’m doing it.
Specific questions lead to much more useful answers than generalized panic.
Discomfort Doesn’t Automatically Mean You’re on the Wrong Path
There’s one more thing I want you to remember if business feels uncomfortable right now: discomfort doesn’t automatically mean you’re doing something wrong.
Sometimes the growing pains show up right before a meaningful shift. There may be things you need to prune. There may be offers you need to simplify. There may be a pivot waiting for you. But a hard month or a slow season is not, by itself, proof that everything you’ve built is broken.
I don’t want temporary discouragement writing the strategy for my next era. Instead, I want to remember who I am and look at the evidence of what I’ve already built. I want to talk to people who can give me thoughtful, human perspective. I want to be intentional about what I outsource to AI, and I want to be willing to release what genuinely no longer belongs.
Then I can get specific about where the friction actually is: who, what, when, where, or why. You may discover that you don’t need to burn the business down at all. You might just need to prune it. And the version waiting on the other side could fit you better than the one you’re trying so hard to hold onto.
Find it quickly:
The seven-year itch (2:13)
You need someone to sort through it with you (5:39)
Be open about the pieces that don’t work anymore (10:01)
It might be time to pivot (10:55)
Mentioned in this Episode:
Episode 185: Ambition Is A Trap Keeping You Stuck: podcasts.apple.com/us/podcast/185-ambition-is-a-trap-keeping-you-stuck
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