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👯‍♀️ Special Guests: Sammy & Gracie (my twin daughters)

🗓️ Recorded after Take Your Kids to Work Day 2026

This has quietly become one of my favorite episodes to record every year.

My daughters—11-year-old identical twins—have been on the podcast a few times now, and each year the conversation shifts a little as they get older, more independent, and more aware of what’s going on around them.

They’ve grown up watching me leave my corporate job and build this business from home. In past years, they’ve “come to work” with me—but this year, they went to work with their dad instead.

So we recorded these conversations separately, and I asked them almost all the same questions.

What came out of it was equal parts funny, honest, and surprisingly insightful.

There’s a lot we talk about on this podcast—systems, strategy, making your business easier to carry—but this episode is a good reminder that sometimes the simplest perspectives are the ones that stick.

If you’ve ever wondered whether the systems running your business are actually helping—or quietly making things heavier—this might be a good place to start. I offer backend systems audits for both 17hats and Flodesk that review what’s working, what’s fragile, and what deserves your attention next. Learn more at kristenlettini.com/audits.

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Lynn Harris, a culture-shifting producer, award-winning journalist, and founder of GOLD Comedy, shares her non-linear path from journalism to comedy to building a community-driven business.

We talk about what it really looks like to run a business when you don’t fit the typical “founder” mold — from testing and growing an idea over time to the role of community, the behind-the-scenes realities, and why you don’t need to have the whole path figured out to get started.

Learn more about Lynn and GOLD Comedy at goldcomedy.com or follow on Instagram @goldcomedy.
(use code GOLD10PERCENTOFF for 10% off if you join GOLD Comedy)

If you’ve ever wondered whether the systems running your business are actually helping—or quietly making things heavier—this might be a good place to start. I offer backend systems audits for both 17hats and Flodesk that review what’s working, what’s fragile, and what deserves your attention next. Learn more at kristenlettini.com/audits.

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You’ve had this happen before.

A potential client says yes.
You send the quote, contract, or invoice…

And then things go quiet.

Suddenly the questions start creeping in:

Did they change their mind?
Did they forget?
Should I follow up?

This moment is incredibly common in service-based businesses — and it’s where a lot of deals quietly stall.

In this episode, I'm walking through the "follow-up gap" — that space between someone saying “yes” and actually completing the next step — and why it often has less to do with interest and more to do with timing, attention, and how we communicate.

If you’ve ever hesitated to follow up because you didn’t want to seem pushy, this episode will shift how you think about it.

***

Free Workshop: Build a Smarter Document Reminder Strategy in 17hats

Design well-timed email and text reminders that feel personal — even though they’re automated.

You’ll learn how to:

• map out reminder timing for quotes, contracts, invoices, and questionnaires
• choose between email and text follow-ups
• refine your messaging so it sounds like you

→ Save your spot

If you’ve ever wondered whether the systems running your business are actually helping—or quietly making things heavier—this might be a good place to start. I offer backend systems audits for both 17hats and Flodesk that review what’s working, what’s fragile, and what deserves your attention next. Learn more at kristenlettini.com/audits.

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Running a business comes with a mental load that most people don’t talk about.

Not the big projects or strategic decisions — but the constant background tracking:

• Who still needs a follow-up.
• Which invoice hasn’t been paid.
• Whether someone signed their contract yet.
• Remembering when a client said they’d “get back to you.”

None of these tasks take long individually, but together they create a quiet mental load that can make running a business feel heavier than it needs to.

So many solopreneurs assume the solution is hiring help — when often the real opportunity is creating better support through systems.

🎧 Listen now to learn how small changes behind the scenes can make your business feel lighter — and a little closer to the fairytale you hoped it would be.

ICYMI

Episode 144: Start at the Front Door: A Spring Reset for Your Business

If you’ve ever wondered whether the systems running your business are actually helping—or quietly making things heavier—this might be a good place to start. I offer backend systems audits for both 17hats and Flodesk that review what’s working, what’s fragile, and what deserves your attention next. Learn more at kristenlettini.com/audits.

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Spring cleaning isn’t about crisis.

It’s about circulation.

In this episode, I’m sharing a behind-the-scenes look at recording during a literal New Jersey blizzard, the decluttering session that unexpectedly boosted my energy, and a confession: I procrastinated this episode harder than I’d like to admit.

Because here’s the truth — dust is just deferred decisions.

And that buildup? It happens in our businesses too.

If things are “technically working,” it’s easy to tolerate small inefficiencies… until the mental load starts to feel heavier than it needs to.

So instead of overhauling everything, we’re starting at the front door.

I’ll walk you through a simple, tactical place to begin your seasonal edit: your lead management process. What happens when someone fills out your contact form? Are they guessing what’s next? Or are you professional by design?

You don’t need a brand-new business.

You need to breathe inside the one you built.

If you’ve ever wondered whether the systems running your business are actually helping—or quietly making things heavier—this might be a good place to start. I offer backend systems audits for both 17hats and Flodesk that review what’s working, what’s fragile, and what deserves your attention next. Learn more at kristenlettini.com/audits.

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You don’t always get the full five-year blueprint in business.

Sometimes you get a clear season.
Sometimes you get a quiet one.
And sometimes you hit a speed bump and think… okay, now what?

This 10-minute solo episode is a grounded reframe for those moments.

Not a checklist.
Not a dramatic pivot.
Just a steadier way to think about uncertainty, slow seasons, and the in-between chapters of building a sustainable business.

If you’ve ever felt tempted to overhaul everything because things felt unclear — this is the episode to come back to.

Tune in for a practical mindset shift on choosing direction over certainty, using planning containers (like a 12-week sprint or seasonal strategy), and why long-term business growth requires calm leadership instead of panic decisions.

And if you’re curious about the Marketing Planning Reset I mentioned in the episode, you can join the waitlist here.

Whether you’re in a clear season or a quieter one, this episode is one to bookmark for the next time you can’t see the whole staircase.

If you’ve ever wondered whether the systems running your business are actually helping—or quietly making things heavier—this might be a good place to start. I offer backend systems audits for both 17hats and Flodesk that review what’s working, what’s fragile, and what deserves your attention next. Learn more at kristenlettini.com/audits.

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February is the season of love — and this year, I want you to turn some of that attention toward your business. ❤️

In this episode, we’re talking about what it really looks like to love your business long-term — not the honeymoon phase, not the Instagram highlight-reel version, but the kind of relationship that actually lasts.

Because most business owners don’t fall out of love with their work.

As your business grows, the logistics grow too. Emails, invoices, scheduling, follow-ups… all the things that quietly take up space and energy. And when there’s no room left, the work you love gets buried.

In this episode, I’ll walk you through:

• Why losing excitement doesn’t mean you chose the wrong business
• How the “honeymoon phase” shows up in both relationships and business
• Why quick fixes (and shiny features) aren’t always the answer
• How intentional design creates room for your spark to shine again
• Why awareness is the most important first step before changing anything

I’m also sharing what I’ve been working on behind the scenes this year — refining my offers, rethinking support, and why system audits have become a non-negotiable starting point in my work with clients.

If you’re using 17hats or Flodesk and your business feels heavier than it should, a simple audit might be the clarity you need. No pressure. No commitment. Just a clear look at what’s working, what’s draining you, and what’s possible.

👉 Book a free consult (your coffee date) to see if an audit is a good next step.

The modern fairytale isn’t about loving every moment.
It’s about building a business you don’t want to leave. 🫶

If you’ve ever wondered whether the systems running your business are actually helping—or quietly making things heavier—this might be a good place to start. I offer backend systems audits for both 17hats and Flodesk that review what’s working, what’s fragile, and what deserves your attention next. Learn more at kristenlettini.com/audits.

Text Kristen your thoughts or feedback about the show

Running a business can feel a lot like working on a puzzle.

You’ve got pieces everywhere — ideas, tools, workflows, client needs — and you know they’re supposed to fit together… but sometimes the picture just doesn’t feel complete.

With National Puzzle Day coming up, I’m leaning into one of my favorite metaphors and breaking down how puzzles and business are surprisingly similar — especially for solopreneurs navigating the messy middle of growth.

In this episode, I’m sharing:

• Why January can feel overwhelming (even when nothing is “wrong”)
• A simple PUZZLE framework to help you figure out what’s missing
• Three different ways people naturally approach building a business
• Why support systems don’t replace your thinking — they protect your progress
• How to stop feeling scattered and start placing the right next piece

If your business feels heavy, incomplete, or just slightly off right now, this episode will help you zoom out, get grounded, and move forward with more clarity.

ICYMI
Ep 140: No Man's Land: Why the Messy Middle Isn't the End of Your Fairytale

🎁 17hats Giveaway (through January 25, 2026)
If leads, contracts, invoices, or client follow-up feel heavier than they should, this is a great time to explore what better backend support could look like.
Details & enter here.

🧩 Completing the Puzzle Subscription
Looking for a fun, low-pressure way to unwind?
A subscription with Completing the Puzzle could be a great fit! They send you a puzzle, you enjoy it, send it back, and move on to the next one (no clutter, no stacks collecting dust).
Use code FAIRYTALE for $6 off your first month.

If you’ve ever wondered whether the systems running your business are actually helping—or quietly making things heavier—this might be a good place to start. I offer backend systems audits for both 17hats and Flodesk that review what’s working, what’s fragile, and what deserves your attention next. Learn more at kristenlettini.com/audits.