Deeper Business

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

May 18 • 5 min read

Would I have started, knowing what I know now?


“Start your side hustle in 90 days!”

“Grow your six-figure business in just 6 months!”

“Go from $2K to $20K months in this one program!”

These are the messages sold to every new (and even more seasoned) expert trying to break out on their own.

While I knew these promises were pretty ridiculous, I thought I had what it took to beat the odds, beat the house, and be successful in business from the jump.

  • I had the corporate pedigree (ex-McKinsey/HBS)
  • I had the energy and capacity (no kids, just one lovable mrloganpup)
  • I had my husband with a salary and health insurance (so I didn’t have as much financial pressure)

What I learned:

Making money on my own was possible (especially if I didn’t care what kind of work I took on).

But building momentum? Working with the right clients, at the right price point, with the right time investment? Oooooh boy did I underestimate how long that would take.

In year one, I had money but zero momentum. I made almost all of my income from corporate consulting as a sub-contractor.

In year two, I had some momentum, but it was misaligned. Most of my revenue came from working as a Fractional COO—highly time-intensive, and not the work that called to my soul.

In year three, I started to see aligned momentum but it was still diffuse. My messaging, branding, and offers were still evolving.

After year four, I finally feel like I'm no longer chasing momentum—I’m moving with it.

  • Clients returning after major successes, being approached for summits and bundles, people outside of my network quoting my work or referring people in my direction.
  • I have a group of business colleagues-turned-friends who I trust in a way I’ve never had before
  • And how I really know I have momentum? I’m excited to dive even further into this body of work, deepening my own expertise and deepening the relationship I have with the Deeper Foundations broader community.

For some of you, this timeline feels short: “I’m still in year 5+ and haven’t built momentum, what am I doing wrong?”

For some of you, this timeline feels long: “No way could I wait that long to build momentum, how can I make it go faster?”

And for others, momentum has been delayed by caregiving, illness, burnout, or just surviving, which simply extends the timeline (and requires radical focus on the most impactful momentum-generating activities).

There are ways to make money quickly—especially if you’re willing to take on anything that pays.

But momentum? That’s harder to rush.

Money often hides a momentum issue:

  • Having 1-2 whale clients or a lucrative sub-contract gig.
  • Enrolling a group of people in one program that continue on to future programs for 2-3 years, even though new clients aren’t coming in.
  • Being the downline or the “preferred partner” from someone who has a marketing machine in place.
  • Tapping your existing network for clients, but then failing to expand your reach

Oh, I tried to make momentum happen faster. I searched for the secret:

  • I hired positioning and messaging coaches
  • I hired admin and social media marketing teams
  • I joined an overpriced mastermind (only one, thankfully), and a number of other programs and communities
  • I spent lots (and lots, and lots) of time and money up-skilling in copywriting, sales, marketing… you name it, I’ve probably studied it.

To only come to the realization that to build real momentum, to build real foundations, there is no secret. No matter how many courses I took, how many coaches I hired, how many shortcuts I chased—the answer always came back to the same philosophy.

There is only intentional effort, over a long enough period of time, for substantially longer than you believe you'll have to when you start.

This is the Deeper Foundations ethos:

Talk to people. Make invitations. Publish regularly.

More often than feels comfortable. For longer than you’d expect.

That’s it. That’s the secret.

  • If you’re in Year 1: Prioritize connection and get in practice with clients. Find a way to make money (even a bridge or part-time job) to reduce financial pressure.
  • If you’re in Year 2: Publish your thinking and point of view more often than feels comfortable, watch for patterns in your work, and expand your network.
  • If you’re in Year 3: Maintain this ethos when delivery picks up and you get busy.

And above all? Focus on what builds momentum versus distracts you and diffuses your efforts. (Like, say, trying to post on all of the social media platforms.)

After years of writing, publishing, delivering, and talking, my point of view has coalesced into a new body of work and brand. So I’m excited to make some announcements.

Welcome to the new chapter: Deeper Foundations.

For many long-time readers, this isn’t anything new. Deeper Foundations has been the name of my cohort program for two years.

But during the wrestling with my premise and positioning last year, and as I wrote the book (which is at the publisher for creative and layout omg), that’s what I realized my whole brand is.

You’re not working with “Jessica Lackey Consulting”. You’re building Deeper Foundations.

The knowledge of how to design and build an expertise-based business, attuned to you.

The intentional focus on fewer, better commitments.

The structures and the rhythms to continue to lay those deeper foundations root by root, brick by brick.

The relationships you need for both acceleration and support.

I don’t know if we can go much faster without exploiting ourselves and others.

But I know we’ll go farther for longer if we build business foundations together.

Explore Deeper Foundations

Want to see what’s changed?

Head to the new site, browse the programs and resource collections, and let me know what resonates.

Thank you for joining me in the first 4 years of business (and this series). I’ll be back next week with more deep dive essays about business.

One of my trusted teachers? Josh Spector.

I've learned so much from Josh's Skill Sessions membership and his newsletter that helps you get clients from your content. He curates amazing resources and is someone I trust to learn from in his podcast, newsletter, and workshops.

NEW EPISODES

Cold Outreach Doesn’t Have to Suck with Jess Lorimer

Most of us have been on the receiving end of a terrible cold pitch. Maybe it was a LinkedIn DM pretending to be friendly. Maybe it was an email that made you feel like a number. No surprise—cold outreach has earned its bad reputation.

But the truth is: cold outreach isn’t inherently bad. It’s just rarely done well.

“Focus on strategic sales activities that get you paid; not marketing activities that make you feel busy.”

UPCOMING EVENTS

May's Dialogue: From Reactive to Proactive in Sales

May 21, 12 pm ET

You don't want to be salesy... but you need more clients. Learn how we can be more proactive in the sales process without being pushy.

  • ​The key steps in new business development
  • ​Strategies to be more proactive at each stage
  • ​How to use your existing marketing to make invitations

Community and Reads

you don't need a record deal, you need a community.

There's still money in music. We see it every day. Mainstream machines are pumping out endless tracks and cashing in. And something I keep noticing is how they leverage collaboration. They've industrialized shared audiences, cross-promotion, and mutual endorsement—things scenes once did organically.

All Twerk, No Play | Bailey Seaborn

When you need a music-filled romance novel - and want to support an amazing human being in the Deeper Foundations world - pick up this book (the 2nd in the series!) and devour it in one sitting. You're welcome.

Jessica Lackey

START INVESTING IN YOUR BUSINESS FOUNDATIONS

Your email preferences:

Change your account details

Unsubscribe from all email


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


Read next ...