Promote Yourself to CEO | Small Business Strategy for Women Entrepreneurs

When you sit down to set your goals for the year or the quarter or even the month, do you make sure that YOU are in the plan too?

After years of running the 90 Day CEO Retreat, there’s one major planning mistake we see again and again. Women who invest in resourcing their businesses without blinking struggle to spend that same time, energy, and money resourcing themselves, because spending on the business reads as ambition and...

Robert Cialdini went undercover at used car lots, telemarketing rooms, and fundraising offices, taking notes on how compliance professionals move a person from no to yes, and he did it because he kept getting talked into buying things he did not want and wanted to know how it was being done to him. The book Influence: The Psychology of Persuasion was the result. He wrote it as a self-defense manual for regular people against manipu...

Somebody handed me a notebook in a conference swag bag in 2014. Rose gold foil. GIRL BOSS on the cover.

I was thrilled. I was in my early thirties with four year old twins and a brand new baby, building a business from the ground up, and after years of apologizing for being ambitious I was watching a whole generation of women get handed permission to want things out loud. Charge money. Take up room. Want more. Call yourself the boss...

When I first started my business, I remember being so frustrated that all the advice was ‘hustle harder’.

I was actively looking for my own coach in the summer of 2010, when my twins were about 6 months old, and I was trying to work out how to move a more traditional boots-on-the-ground, in-person local consulting practice to an online model using GoToMeeting and Skype (yep – we were in the early days of being able...

"I need Spicy Rach."

Gabi Day said that to me on a call about ads, and I knew exactly who she meant. Spicy Rach is the version of me that shows up when I am fired up about something and want to see it change. She is also the version I have spent years keeping mostly off the internet.

Gabi does not have that problem. She shows up as 1000% herself all the time, and that is the whole reason her marketing works.

So when we both spent the ...

There was a three-ring binder in my dad's insurance agency and we called it the "office bible". That binder was a business brain about thirty years before anyone thought to sell you one.

A woman who worked for him built it. Every task she did had a checklist in that binder, so when she wasn't there, somebody else could sit in that front seat, answer the phone, and take a payment from whoever walked through the door. This was the nin...

Two overlapping circles on a piece of paper. Human only on the left, AI only on the right, and the overlap in the middle where almost nobody is spending any time at all.

That is the whole exercise. My cousin Kendall gave me the version of it that ended months of AI pushback inside her tech company, and I tell that story at the top of the episode. What matters here is what it does.

This is episode three of Human First: AI for High-Tru...

A few months ago I made three photorealistic images of myself, put my logo on them, and posted them to Facebook.People laughed. They were supposed to. I had run my real photo shoot images through a meme generator with a 2,000 character summary of my business, and what came back was, in my head, cartoonish.

 Obviously fake. A joke.

Then a couple of comments came in. This is kind of creepy. This isn’t you, right?

I went looki...

Most of the conversation about AI is happening at two extremes. Founders bragging publicly about the payroll they cut, and founders refusing to touch any of it. Both are missing the point, and neither one leaves you with an answer you can actually run a business on.

So I spent six months deep diving into AI so I could form my own thoughts. Three programs, an intensive, and a lot of building. Not reading about it. Not collecting othe...

There is still a block sitting on my calendar from the second week of July that says “Record new podcast episodes.”

I never moved it. I sat down in front of it most mornings, pushed it to the next day, then to the next week, and eventually I stopped pretending and just let it sit there being wrong.

My granny died while my family was in Italy – just 6 months after my mom passed away. 

So instead of returning home...

You come home from a planning day lit up. Six hours of clarity, a wall of Post-its, a quarter that finally makes sense. Then you sit down with your team, and somewhere between your head and their inbox the whole thing flattens into a to-do list nobody has the context for.

Elise Arsenault knows that exact moment. She built The Global Actor into a training program the audiobook industry has come to trust, with ten of her graduates nom...

Adrienne Loker was certain her group therapy practice needed more marketing. Her numbers said otherwise. Here is what actually turned her business around.

Most therapists believe the path to growth is hiring a team and handing off clients. Adrienne did exactly that, and the plan that looked perfect on paper came apart the moment real people and real life entered the picture. People got licensed and left with their caseloads....

Right now, as you hear this, I am probably lounging by a pool in a villa in Tuscany, watching my kids and their cousins splash around while I have my full Under the Tuscan Sun moment. There is a family wedding tomorrow, a welcome dinner tonight, and still another 2 weeks of exploring Florence and Rome ahead.

What I am not doing is refreshing my inbox in a panic, wondering whether everything is quietly falling apart back home. I alre...

There is a specific kind of quiet that gets under your skin in July, and it has nothing to do with a slow, lazy afternoon. It is the quiet of your bank account. Clients are off on vacation, nobody is starting anything new, and you can feel the revenue dip coming the way you feel a storm before it lands.

I used to brace for that quiet too. Now I don’t, because of one strategic move I make almost every summer. It is the same rea...

I grew up in the river realm of Virginia, where everyone either had a boat or knew someone who did, and summer meant Friday afternoons out on the water before the weekend even started. The reason my family got to do that was simple. My dad ran summer hours in his business, and by noon on Friday the office was empty and everyone was gone.

I didn’t clock it as a business decision back then. I just knew we were a little different...

My three teenagers are home for the summer, the calendar cleared out the last week of May, and like a lot of business owners I could feel the pull to write the next two months off and call it a season.

I’m not doing that, and I don’t want you to either.

After almost 20 years of running this business, here’s what I’ve watched happen every single year. The women who disappear completely in June and July are the ...

There is a note blocking off the last week of May in my calendar, and it is yelling at me. Last week of school. Do not plan anything. All caps. Too many exclamation points. When I open it, past me has left the longer version: be nice to yourself, Racheal, there will be concerts and awards and kid stuff, the twins get out by one most days.

I wrote that a year ago, for the version of me who would forget. And she always forgets.

Here is...

If the plan you wrote down in January no longer matches the year you're actually living, you're not behind. You're just due for a review.

This is the time of year where I see most women entrepreneurs do one of two things. They abandon the plan entirely and start running on default, or they white-knuckle a plan that stopped fitting their reality months ago. Both end the same way: a Q3 where nothing feels like it's working and you can...

Most women don’t realize they’ve built a ceiling around their next opportunity until they’re standing right in front of it.

It looks like turning down a speaking opportunity because you have nothing to wear. It looks like saying no to the podcast interview because your hair needs to be colored. It looks like quietly opting out of visibility because the version of you that needs to show up doesn’t feel like th...