Deeper Business

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

Aug 10 • 5 min read

The one thing I (kind of) miss about corporate


When I left my corporate job, I was clamoring to get out.

I’d been plotting my exit for years: frustrated by the culture, exhausted by the politics, and ready to do things my way.

I knew I’d miss colleagues to talk with every day and the paycheck that landed on time.

But what I didn’t expect to miss?

The guardrails that my job put on my pace.

Outside forces to regulate my speed

When I worked at Nike, I had a big idea—a new system and dashboard for reviewing our sales plans. It was a need everyone saw, but no one’s job to create. My VP told me to go for it.

Of course, it didn’t happen overnight. I had to:

  • Pitch the idea to get funding for a developer
  • Hire the project manager and assemble the team
  • Create specs, timelines, and lead the change process

Each step took weeks or months. I couldn’t just barrel through, working nights and weekends nonstop, even though I was ready to go now.

At the time, I hated it. I’d get frustrated at the approvals that took forever and the data governance leaders who seemed to slow everything down. (Sure sure, “data integrity” is important).

Looking back? Those slowdowns stopped me from taking on too much, too fast. The system—including my managers—protected me from my own “just keep pushing” instincts.

Now? I have the freedom to do whatever I want.

That freedom is exhilarating. It’s also confronting.

If I get a new idea for a course or workshop, I can spin it up in a few hours and launch it, without considering if I actually have time to finish creating the thing and promote it properly. Ideas always take more time to execute than I expect.

But without someone else telling me “not now” or “wait until next quarter,” I have to pace myself, hold myself back in some cases, and—most importantly—honor the pace I’ve set.

For you: What protects you from running too fast or taking on too much?

A minimum speed and rhythm

Corporate also gave me deadlines.

In my role, sales plans were due Week 1. Inventory plans in Week 2. A leadership review in Week 4. Every month.

Like it or not, I had to keep shipping. The pace was predictable (relentless and unachievable, but predictable).

And when I didn’t like the pace, I could get mad at my bosses, not myself.

Now? I have to decide how often I send newsletters, do my bookkeeping, clean up my CRM. I must protect time for the projects I’ve committed to and decide when they’re good enough to go.

And it’s not just about setting that pace. I have to uphold it, season after season, adjusting the pace as life changes.

If I miss a newsletter, there’s no boss to remind me. If I delay my metrics review, there’s no leadership meeting I’ll be unprepared for. The responsibility is mine, start to finish.

For you: If you don’t have a way to define and uphold your minimum pace each season, you risk long stretches of no visibility, untended and unruly systems, and zombie projects that ultimately slow your business down.

Being your own pace car

In NASCAR, the pace car keeps the race safe after accidents or at the start of a race. Too fast? It slows everyone down. Too slow? You get flagged and pulled off the track.

When you work for someone else, your organization sets the pace standards for you, regardless of if the overall pace is punishingly fast or frustratingly slow.

But on your own? You have to set—and uphold—a pace range you can sustain, adapting that pace each season as your life changes.

I have a set of practices that serve as my "pace car":

To keep me from doing too much:

  • A high-level launch calendar for the next 6–9 months; if something new emerges or delays, something else must shift
  • A prioritized projects list with no more than three active projects at a time; everything else goes on an “idea board”
  • Running new ideas by my Voxer board of advisors before I commit

And for upholding my commitments:

  • Reviewing metrics and doing sales outreach every month live with Deeper Business Members.
  • Co-hosting a podcast with Meg so we don’t have to carry it all by ourselves
  • Hiring support for bigger projects or contract work—and hitting their deadlines.

The freedom to do whatever you want is exhilarating—until it isn’t.

Without defining your own guardrails, you can push yourself into burnout or drift off course.

How will you set and honor your pace?


If you’re looking for that pacing and accountability, the waitlist for the Fall Define Your Foundations Cohort is open. Together, we’ll design your business and its rhythms for a pace you can sustain—and we’ll do it together.

Enrollment opens in August, with the program starting September 18. The waitlist gets first access and a discount.

NEW EPISODES

The shifting role of content in our businesses

Meg and I are shifting our business models, each in different directions.

But in both of our businesses, content (and the act of creating content) is still very important in our businesses, but in different ways. From content as teaching assets, to being found in AI, to helping us define our signature linguistic styles, we explore how we create content, why we create content, and how we use it throughout the entire customer journey.

UPCOMING EVENTS

Each month we'll discuss a chapter in my upcoming book, Leaving the Casino: Stop betting on tactics and start building a business that works.

Each dialogue is 12-1pm ET.

August 20: Your Business Model

September 17: What's the Impact You Want to Have?

October 22: The Responsibility You Carry

Community and Reads

When Your Business Has ADHD, Too | Diann Wingert ADHD-ish

Ever felt like your business is just as “ADHD-ish” as you are? This week on the ADHD-ish Podcast, Diann dives into an eye-opening conversation with Diane Mayor about how ADHD traits show up in our business, for better or worse. Diane has the kind of ADHD that makes systems and structure make sense, but she also knows that if it’s not fun, it’s not going to happen, so she makes sure that it is.

If your business model looks sparkly on the front end, but is duct-taped together behind the scenes, don’t even think about scaling before taking the lessons in this episode to heart.


Does answering the question, “What do you do?” send you into a downward spiral?

My friend Jamie R Cox (brand and marketing strategist and green-haired girlie) is running a 5-week group program called Brand Clarity Lab—and if you’re a B2B service provider who’s tired of second-guessing your messaging or avoiding marketing altogether, this could be exactly what you need.

You’ll walk away with a clear brand foundation, expert feedback, and a plan for showing up with confidence.

Jessica Lackey

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


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