The Devil Wears Asana...

Hello there, my fellow enterpreneurs! Let me tell you about Keyla.

Keyla is a Leadership Life Coach. Not the generic "live your best life and journal your feelings" kind, the real kind. The kind that takes burnt-out executives, mid-level managers drowning in their own teams, and first-time founders who suddenly have twelve people reporting to them and absolutely no idea what to do about it, and turns them into actual leaders. The kind people drive across the city for. The kind whose clients send referrals before the engagement is even over.

By every measure that matters in her industry, Keyla was exceptional at her job.

And her business was a complete, spectacular, almost artistic disaster behind the scenes.

I found this out the way I usually find things out, she told me, with the particular exhaustion of someone who has been holding it together in public for so long that the moment they're in a safe room, everything just comes out. "I help executives become better leaders," she said, "while I personally cannot lead my own business out of a paper bag." She laughed. It was the kind of laugh that's about 40% funny and 60% crying.

I asked her to walk me through a typical day.

She woke up and checked her phone before her feet hit the floor, emails from a client in a different time zone who had questions about their session notes. She made coffee, opened her laptop, and spent forty-five minutes trying to find a document she definitely saved somewhere. She had three discovery calls booked, two of which were on different video platforms because she hadn't sorted out a unified system, and one of which had the wrong time zone because her Calendly was, and I quote, "doing something weird." Between calls, she wrote an Instagram caption, responded to six DMs, manually sent an invoice she should have sent two weeks ago, and started a blog post she didn't finish. By 7pm she had coached brilliantly for a combined four hours and spent the remaining six hours doing everything except coaching. She ate dinner while answering emails. She went to bed thinking about the proposal she hadn't written yet.

"That," I told her, "is not a coaching business. That is a one-woman emergency response unit."

She nodded very slowly, in the way people nod when someone has just described their life back to them with uncomfortable accuracy.

Now here's the thing I want you to understand about Keyla, because this is where her story gets genuinely interesting. Her problem wasn't that she wasn't good enough. Her problem wasn't even that she was disorganised, she was actually a deeply structured, methodical thinker, which is precisely what made her brilliant at developing other people's leadership. The problem was that all of that structure existed entirely in her head, and her head was already full of twelve clients' goals, progress, setbacks, and breakthroughs. There was simply no room left for running an actual business.

The first thing that struck me when I looked at her marketing was that it was essentially a very expensive wish. She posted on Instagram when she had time, which meant sporadically and at random hours. She had a website that described her services in the kind of language that could apply to roughly half the coaches on the internet, "I help you unlock your potential and become the leader you were meant to be." Lovely sentence. Completely invisible in a market of 145,000 certified coaches worldwide, a number that has doubled since 2019. Doubled. Her email list had about thirty people on it, and when I asked her when she'd last sent something to them, she went quiet for a moment that told me everything.

She wasn't marketing. She was hoping. And hoping is a terrible marketing strategy, even when you're genuinely outstanding at what you do.

What made this particularly painful was that her niche, leadership coaching, is one of the most lucrative in the industry. Executive coaching alone is worth billions. The people she worked with had real budgets, real urgency, and real willingness to pay premium rates for someone who could actually help them. But Keyla was charging rates that, when divided across her real working hours, came out to roughly what you'd pay a reasonably competent delivery driver. Not because her work wasn't worth more, it absolutely was, but because she'd set her prices when she was starting out, slightly terrified that anyone would pay at all, and then never revisited them because revisiting them would require confronting the number and that was uncomfortable. So she just kept charging less than she was worth, working more hours than she should, and wondering why the business felt so relentlessly exhausting.

I've seen this pattern so many times I could write a very depressing song about it.

Then there was the technology situation, which I can only describe as creative chaos. She had Google Calendar, Calendly, a CRM she'd signed up for and never set up, a separate spreadsheet that was supposed to be her CRM, Zoom, Google Meet, a WhatsApp group for some clients, and sticky notes. Physical sticky notes. On her monitor. In 2025. When I asked how she tracked client progress between sessions, she pointed at her head. When I asked where her contracts lived, she pointed at a folder on her desktop called "Important Stuff, DO NOT DELETE" which contained 847 files in no particular order.

The technology wasn't her enemy. She'd just never had anyone sit down with her and build a system that actually worked for the way she worked. So she kept accumulating tools and none of them talked to each other and the whole thing sat there generating anxiety instead of efficiency.

And running underneath all of it, quietly sabotaging everything, was the fact that Keyla was trying to do this entirely alone. She was the coach, the marketer, the accountant, the tech support, the content creator, the customer service team, and the project manager, all at once, all the time, with no backup and no days off. Her holidays, such as they were, consisted of checking her phone from nicer locations. She hadn't taken a sick day in two years, partly because she physically couldn't, if she stopped, everything stopped, because everything ran through her and only her. She had built, without meaning to, a business that was 100% dependent on her being present and operational every single day. That's not a business. That's a very elaborate trap.

I told her this. She looked at me and said "I literally coach people on sustainable leadership and I have somehow built myself the least sustainable leadership role imaginable."

I told her the irony was world-class.

Here's what we did. We started where I always start, by looking at what was actually there. Who were her best clients? Not the most frequent or the most vocal, but the ones who got results, paid well, came back, and told other people about her? Almost without exception, they were mid-to-senior level managers in tech companies who had recently stepped into leadership roles and were terrified of getting it wrong. Not CEOs. Not founders. Not "anyone who wants to be a better leader." A very specific person at a very specific moment in their career, experiencing a very specific kind of fear. That was her real niche, sitting right there in her own client data, completely invisible to her because she'd never stopped to look.

Once we had that, everything else started clicking into place. Her messaging stopped being generic inspiration and started being a direct conversation with exactly that person. Her content, which we systematised into a proper calendar with actual strategy behind it, started speaking to the things that kept those managers awake at night. Her email sequence, which we built from scratch and set to run automatically, walked new subscribers from "I just found this person" to "I need to book a call" without Keyla having to touch it. Her pricing, which we rebuilt into a proper package structure based on outcomes rather than hours, went up significantly. Her discovery call volume went down slightly. Her revenue went up considerably. Fewer wrong-fit clients, more right-fit clients, at rates that actually reflected what she was delivering.

We connected her tools so they talked to each other. Booking to payment to onboarding to session notes to follow-up, one smooth sequence, automated, consistent, running in the background whether Keyla was in a session or asleep or, eventually, actually on holiday. A real one. Where she didn't check her phone.

She sent me a message six weeks in. "I just had my first Saturday in two years where I didn't work," it said. "I didn't know what to do with myself so I went for a walk and it was very confusing but also quite nice."

That's the thing nobody tells you about getting your operations right. Yes, the revenue goes up. Yes, the stress goes down. Yes, the business gets more efficient and more scalable and all the things you're supposed to want. But the part that actually matters, the part that made Keyla become a coach in the first place, is that she got her energy back. The sessions got better because she wasn't running on fumes. The clients felt it. The results got better. The referrals increased. The whole thing moved upward because one person stopped trying to do everything and started focusing on the thing she was actually exceptional at.

She helps leaders become better leaders now. Turns out she just needed someone to remind her that applied to her too.

Does any part of Keyla's story feel uncomfortably familiar?

The chaos backstage while everything looks polished out front. The hours that disappear into admin. The pricing you've been meaning to revisit. The system you've been meaning to build. The holiday you've been meaning to take.

If you're nodding, let's talk.

I offer a complimentary 30-minute session where we take an honest look at what's actually happening in your business: where the time is going, where the gaps are, and what it would concretely take to build something that runs without running you into the ground.

No pitch. No fluff. Just a real conversation with someone who has done this before — and who will tell you the truth even when it sounds a little bit like your own irony being read back to you.

Book your complimentary session here 

You didn't become a coach to do data entry at midnight. Let's fix that.