Past, Present, Future: 3 CEO Moves You Can Make Today

Ever said “I’ll *never* grow a team” or “I’ll *always* be a solopreneur”?

WARNING: Never say never. (Also, never trust a woman who says she’s not expanding her business while creating another color-coded Trello board.)

When I started Alison Leigh OBM LLC, it felt perfect. Just me, running the show. 

A one-woman tornado of systems, strategy, and sass. 

But somewhere between a cross-country move (bye California 👋, hello lower tax obligations) and launching my AI-fueled group program, something shifted.

A conversation I had six months ago with a friend planted a seed I didn’t even realize had taken root: maybe it was time to move beyond a personal brand.

Because the truth is, I’m not just a solopreneur anymore. I’m building something bigger than me.

Something other people can step into, grow with, and carry forward. Something that could, dare I say, run without me someday…

(my inner Monica isn’t quite ready to accept that possibility yet)

Enter: LeadSmarterCo

The name, the mission, the big CEO energy… 

No capes, but we (as in “the royal we”) do believe in killer systems and onboarding that doesn’t make new hires cry.

Because it’s not just about me anymore. 

Was it scary to let go of the old name & personal brand identity? Yep.

Did I do it anyway? Also yep.

Did I spiral into an identity crisis, obsessively reorganize the new pantry, and eat three brownies in under 90 seconds? Obviously.

This popped up in my feed this week and it was EXACTLY what I needed to see in that moment…

Let’s talk brain science for a sec.

Your brain is basically a threat-detection machine. It doesn’t care about your goals. It cares about survival. Which means any big change, even the GOOD kind, gets flagged as danger. 

Cue the procrastination, imposter syndrome, and decision fatigue.

So if you’ve ever felt like you’re dragging your feet on next-level moves, it’s actually totally normal because you are literally wired that way.

But here’s the hack: Your brain can be re-trained through exposure, clarity, and tiny brave actions that tell it, “We’re safe. We’ve got this.”

You don’t need to bulldoze your fear. You just need to confuse it with momentum. (Struggling with that bit? Que last week’s newsletter in case you missed it). 

Now, with that context…

Welcome to the Time Travel CEO Exercise™ 

(it’s not actually trademarked, but it sounds cooler that way)

Past You:

Open up your calendar or your camera roll from two years ago. That version of you had different challenges, different wins, and a different vision.

Maybe you were grinding it out solo, or maybe you were just getting your momentum. Either way, acknowledge the progress, the pivots, and the lessons learned.

You’ve evolved, and that matters.

Present You:

Write a quick tweet (to yourself) about what your business feels like today.

Maybe you’re deep in momentum and riding that high. Take a snapshot of that. Or maybe you’re in a weird limbo, unsure what’s next.

Either way, reflect honestly. Then ask: is this the business you meant to build or the one you defaulted into?

Future You:

Now open a blank doc and write a memo from your future self, 2 years ahead, saying thank you for the decision you’re making this week.

What changed? What finally worked? How does it feel to have clarity and confidence instead of chaos?

Remember that Future Letter to Myself that Made Me Ugly Cry newsletter I shared a few months ago? I’m already living some of it out, and that is sooooo cool!

This week’s challenge:

Complete all 3 Time Travel CEO steps, then take it one step further:

Grab a coffee (or a cocktail, no judgment) and reflect on these three prompts:

1.   What did your business look like two years ago?
2.   What does it look like today?
3.   What do you want it to look like two years from now?

Post your “Future You” memo to social if you’re feeling bold (I double dare you) because your future isn’t created by vision boards alone. It’s built by bold moves in boring moments.

Your next level isn’t out there somewhere. It’s already in motion. You just have to keep steering the ship and the future CEO version of you? They’ll thank you for starting now.

Speaking of which, I’m hosting my next live Be Your Own Boss Better webinar on August 21st. It’s everything I wish someone had taught me when I was hustling toward six figures with a glorified to-do list and a prayer.

I’ll show you how to think and act like a 7-figure CEO before you even hit six. No vague mindset mantras. Just real strategies you can actually use now.

Get all the details and register here → www.leadsmarterco.com/webinar

Your business is allowed to evolve. You’re allowed to outgrow what once worked.

Let’s stop surviving and start leading smarter.