Deeper Business

Build your business - and your business-building intuition with foundational frameworks and practical application.

Jun 07 • 4 min read

How to try again


Many of you joined my newsletter in the past year, from Leaving the Casino, word of mouth, or other summits and bundles I’ve done.

Which means you’ve seen me at my best.

You’re seeing me as Sandra Bullock in Miss Congeniality post-makeover

After copywriters have pulled out the gems I say into web and email copy.

After I've had specialist graphic designers, brand designers, and illustrators transform my brand assets and illustrations over the past 6 years at least a few times.

After I’d codified my point of view and had a lot of experience delivering to hundreds of experts.

At this point, most of you are seeing me 10 years in. And the only reason I’m here is because I kept trying.

Only a very select few of you saw the preceding attempts.

You didn’t see me in my pre-business makeover days.

Did you know I actually started my entrepreneurship journey as a holistic nutritionist a decade ago in 2016?

And then got certified as a coach and launched a leadership coaching business as a side hustle from 2017-2021 when I was still employed in corporate?

Yes, I built a “funnel”. Yes, I ran ads to a 30 day “calm down challenge!” on Facebook. (No, it didn’t work for me back then either).

Then I leapt out on my own as a Fractional Chief Operating Officer for 3 years…

I had a tiny mailing list of 150 people. Four people attended my first workshop. I launched a Quarterly Planning Retreat back in 2022 that had exactly one participant, who got a lovely personal strategy session.

So when it feels like no one comes to your first events… been there.

And ONLY after 10 years of trying — writing the blog posts, joining the networks, testing out so many offers and rounds of copy and delivering over and over — did I finally land on the right brand, client, and service model designed for me.

This is why I’m excited to recommend my friend Steve Kamb’s new book: How to Try Again.

I’ve followed Steve’s work since 2013, as I stumbled across his company NerdFitness.

Thirteen years later, I got to meet him in person and offer to review an early copy of this book.

And Steve’s whole philosophy, grounded in fitness but applicable to life, is rather than helping people succeed with more discipline, we help them fail with more compassion.

Steve’s new book is called How to Try Again because, "it’s not just “trying again” that matters, but how we try again that makes all the difference."

Instead of simply building a perfect workout program to follow, we help clients get back on track after a sick dog causes them to miss a week.
Instead of shaming people for eating fast food with their kids, we help them fit fast food into their flexible weekly plan.
Instead of chasing temporary changes for temporary results, we help our audience make sustainable progress with sustainable results.

Steve’s philosophy is grounded in 4 components called a PACT:

  • P: Pause — How to Not Make Things Worse
  • A: Accept — Why “Normal” isn’t Normal, and That’s Normal
  • C: Change — What’s Different This Time
  • T: Try — Start Ugly and Get Good

This is as relevant in the business space as it is in fitness and nutrition.

Most business advice assumes you’ll execute perfectly.

You’ll publish every newsletter.

You’ll follow up with every lead.

You’ll never get sick, burned out, distracted, discouraged, or overwhelmed.

But that’s not real, and certainly not congruent with the Deeper Foundations ethos.

Real businesses are built by people who miss weeks, lose momentum, change direction, and have to start again.

And real businesses get built by people who can stay in the arena over the years and try again.

Steve’s book is releasing June 16, but we all know that pre-orders are good for the soul (and good for the publishing rankings). The book is funny, easy to read but challenging to how I think about change, and super supportive.

You can order the book here!

NEW EPISODES

Email for service providers vs. creators with Bev Feldman

In this episode, we’re joined by returning guest Bev Feldman, email marketing strategist for credentialed professionals at Your Personal Tech Fairy.

We talk about why most credentialed pros either email too rarely (out of spam fear) or too often (copying content-creator cadences), why “top-of-mind selling” works better than launch selling for service providers, and the difference between a newsletter (selling ideas) and email marketing (selling products and services) — and why that distinction matters when everyone is being herded onto Substack. We also get into welcome sequences, the Expert’s Paradox, the Gmail open-rate drop, and what happens to a sales call when a Services Guide does the qualifying for you.

Community and Reads

Breaking Down Jessi Jean's $1.2M Product Launch | Build with Becky

I've only recently heard about Yapping, and only heard about Jessi Jean this week. Becky does a great job of breaking down how Jessi grew her account, how the launch happened, and what we can learn even if we don't have 350K followers.


The Fee Conversation your Consulting Firm is having too late | David A Fields

As a consultant, you may be inclined to defer any mention of budgets, fees or pricing until after you’ve articulated every detail of your spectacularly compelling approach, and preemptively dismissed every major objection.
Once your prospect is swooning over your capabilities and credentials, he’ll pay whatever fees you suggest, right?
Uh, no.
When it comes to discussing fees, clients jump in too early and consultants often wait too late.
The ideal time to broach the topic of budgets and fees is before you dive deep into the benefits of working with your consulting firm, and before you outline possible solutions.

Jessica Lackey

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Build your business - and your business-building intuition with foundational frameworks and practical application.


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