This episode is for the ones who are done dimming their light. I sit down with the phenomenal Kelli Preston—branding mentor, creative rebel, and self-trust whisperer—for a soulful, no-fluff conversation on building a business (and a life) that reflects all of you.
✨ We talk about:
Navigating risk, burnout, and breaking the rules
Honoring your body and your boundaries while building your brand
Letting go of borrowed blueprints and over-investing
How personal branding is really about coming home to yourself
Whether you're still trying to make your 9–5 work or you’re in the messy middle of a pivot, this one’s for you.
You Don’t Need Permission To Be Seen
Branding, Risk, and Self-Trust with Kelly from Square Peg Studio
Today’s episode is for the women who feel like “too much” and not enough at the same time. The solopreneurs stuck between Canva meltdown and “I can’t afford an agency.” The creatives who secretly want to be seen, but feel safer staying small.
My guest, Kelli Preston is the unapologetic brain behind a branding studio that’s all about building a legacy that feels like you and actually makes you money—without flattening you into a template.
She’s also:
A former esthetician and health coach
A self-taught website designer and copywriter
A skincare snob and olive-tree-people evangelist
A midlife phoenix in the middle of her own next evolution
And underneath all of that?
She’s obsessed with one thing:
Women feeling safe enough to be fully self-expressed.
Let’s get into it.
From Brick-and-Mortar Spa to Self-Taught Brand Studio
Before the fonts, logos, and “ditch the Canva crisis” vibes, Kelli was:
An esthetician
A health coach
Running a mini spa in Portland, Oregon
Then she had her son.
Suddenly the in-person life—brick-and-mortar, hands-on services—didn’t match the reality of parenting. She needed something more flexible. That’s when she started shifting online and realized:
“I needed a new website… and I had no money to pay someone (again) to redo it.”
So she sat down and did the one thing she didn’t “identify” as:
She opened her laptop
She taught herself
She built the site anyway
She fought the urge to throw the computer out the window 😅
In the process, she realized:
“I did not think I was techie. I did not consider myself creative or a designer. And then I discovered I was all of those things—because I stayed the course.”
A friend saw her DIY site, loved it, and hired her to:
Write copy
Design a website
Help launch a cookbook
That one “I’ll figure it out” moment turned into client after client after client.
No design degree. No formalized path. Just desire + self-trust.
Desire vs Fear: How Are You Actually Making Decisions?
One of my favorite parts of this conversation was how clearly Kelli described the difference between fear-based decisions and desire-based decisions.
Fear sounds like:
“No one will buy from me if I don’t take this course.”
“I can’t charge these prices until I get this certification.”
“I’ll never be legit without XYZ program/coach/framework.”
And you can feel it in your body:
Constriction
Pressure
“I have to, or else…” energy
Desire feels like:
“I can’t wait to do this.”
“I’m exhausted, but I still want to open my laptop and create.”
“This feels like play, even when it’s hard.”
Early on, when her son napped, she would:
“…run to my laptop and start creating. I needed to create.”
That’s desire. That’s divinity. That’s the pull.
And she makes a powerful point:
When you invest from fear, panic, or “I’m broken, please fix me,” you don’t just risk your money—you risk your inner compass.
Over-Consuming, Over-Investing, and Losing Your Inner Compass
Kelli is very honest about what happened after the initial magic:
She started taking all the courses
Signing up for certifications
Outsourcing before her business was truly ready
She says she:
Put a ton of financial pressure on the business
Took on debt in the name of “this will make me legit”
Slowly disconnected from the ease and magic of trusting herself
And this is the part that hit me:
“We hope that if we invest, they will tell us we’re going to be great. We think they’ll take the burden of failure away from us.”
Oof.
The truth?
You can’t outsource your self-trust.
Over-complicating your business often shrinks your free time and increases pressure.
Pressure and desperation leak into your messaging.
Instead of:
“I’m so proud of this offer. I can’t wait to help someone with it.”
The energy becomes:
“Please buy this. I need to pay this debt off. I need this to work.”
Same business, very different nervous system.
Entrepreneurship Is Risk + Resilience (a.k.a. The River of Misery)
We talk about risk a lot in this episode—how triggering it can be, especially for women who’ve been taught to stay safe, compliant, and grateful.
Kelli names it clearly:
“Entrepreneurship is your resilience with risk.”
She uses:
Strength training as a metaphor
The “river of misery” (that in-between where the old self doesn’t fit, and the new self isn’t fully formed yet)
You don’t get stronger by thinking about lifting weights. You get stronger by:
Showing up on days you don’t see results
Being sore, confused, tired
Trusting that the ice cube is melting even when it still looks solid
Same with business:
Nobody likes your post?
No one responds to your email?
Your offer flops?
You either decide:
“Nothing’s working, I should quit.”
or
“I’ll figure out why this didn’t land, make adjustments, and try again.”
That second voice—“I’ll figure it out”—is your entrepreneurial spine.
If You Don’t Want to Be an Entrepreneur (But Still Want Freedom)
One thing I really appreciated is how Kelli did not romanticize entrepreneurship as the only path.
She’s honest:
Entrepreneurship is constant problem-solving.
Your brain is always spinning: funnels, tech, content, offers, visibility.
There is a kind of freedom in a 9–5 that many entrepreneurs miss.
So what if you’re listening and thinking:
“I don’t want my own business. I just want more freedom in my job.”
Her advice:
Don’t leave a job hating it.
If you can, leave from a place of: “I made this as good as it could be.”
Ask: How can I make this job work for me while I’m here?
Even if:
You’re using that job to fund your life
To pay for the things you love (travel, food, hobbies, therapy, classes)
To give you stability while you figure out your next thing
The key is noticing your narrative.
If every day is:
“I hate this. Everyone’s the worst. I’m trapped.”
The only person suffering is… you. And that bitter energy makes it hard for better opportunities to find you.
Instead:
Reframe: “This job is funding my freedom/time/expression.”
Start a small side project if that feels safe (writing, art, a course, a Substack, whatever).
Let your current role be the container that funds the next version of you.
Midlife, Skincare, and the Second Coming of Self
Right now, Kelli is in what she calls midlife rebirth:
She’s 44
She feels the most alive, energized, and truthful she’s ever felt
She’s noticing how warped our stories about aging are
She found a skincare line she genuinely loves—ingredients, mission, environmental values, how they treat workers—and it woke up the esthetician in her again.
This time, though:
It’s not about hiding age.
It’s about vitality, visibility, and pleasure.
It’s about community and another path to financial freedom through direct sales.
She’s blending:
Branding + self-expression
Skincare + wellbeing
Aging + visibility
Direct sales + personal brand
And she’s asking:
“What does it look like to have a personal brand that holds all of you—your disciplines, obsessions, age, body, story—without chopping off the parts you think are ‘too much’ or ‘off-brand’?”
Because in this era?
The most magnetic thing is the person, not the polish.
Women, Memoirs, and the Power of Telling the Truth
We also talked about memoirs—specifically women’s memoirs—and how they influence courage.
Kelli’s been deep in books like The Many Lives of Mama Love and other raw, honest life stories. What strikes her is:
The bravery it takes to tell the truth publicly
The women reading their own audiobooks, in their own voices
The way their honesty reframes our excuses
She said something like:
“If she can talk about being raped by her father in a book she narrates herself… I can write an honest Instagram post about skincare.”
That’s the scale shift.
Your “little” truth-telling online might feel small, but:
It sets you free.
It quietly sets someone else free.
It helps normalize the mess, the shame, the complexity.
And in a world of AI, auto-generated content, and endless templates?
We’re hungry for the real-real.
That’s personal branding now:
Less “perfect expert”
More “honest, evolving human”
Grounding, Nervous Systems, and the Power of the Pause
We closed with something deceptively simple but huge:
When emotions are high, intelligence is low.
Whether you’re:
Over-hyped and wired
Anxious and spiraling
Desperate to “fix your life” tonight
Your brain is not in its best state for decision-making.
So her first step for anyone feeling stuck, scared, or burnt out:
Ground.
Get back in your body.
Regulate before you decide.
That might look like:
A walk, a run, or lifting weights
A guided meditation on YouTube
Breathwork, journaling, or lying on the floor
Vacuuming with a meditation playing in your ears (yes, really)
You don’t have to love the language of “nervous system,” “somatic,” or “embodiment” for the truth to still be true:
Your power lives in the pause.
From that calmer place, you can:
Notice your thoughts
Question the fear narratives
Make choices you don’t have to “clean up” later
If you’re in a season of:
Rethinking your work
Considering a business
Staying in your job but wanting more agency
Or just wanting to feel more you in your life—
I hope this episode with Kelly reminds you:
You don’t need permission to be seen.
Your story is allowed to be messy, in-progress, and self-taught.
Risk is uncomfortable, but you don’t have to do it from a dysregulated place.
Your honesty is medicine—for you and for someone you don’t even know yet.
Until next time,
be well, be gentle, and remember: you’re allowed to take up space. 💛
About Kelli Preston
She helps female founders cut the fluff, find their real voice, and build unforgettable brands—fast. With a sharp eye and a smart take on using AI, Kelli turns branding into a bold act of self-trust.
