Personality-led business building, positioning and pivots.
In conversation with Jessica Lackey.
ICYMI, I’m back on Substack! Writing on Wednesdays to help you define what you truly want from your business. Expect advice, frameworks from my coaching practice and guest interviews.
Welcome, friends, to a new interview series where I ask entrepreneurs to divulge details behind their business shifts, new seasons and pivots.
Today, we’re joined by the incredible business and operational strategist Jessica Lackey. Read on for an interview with Jessica on her decision to pivot, in search of more alignment.
… by way of *bonus* content…
Jessica and I both have YouTube channels so decided to film a chat, as two business coaches with different focuses & approaches, about how personality impacts business building. This is central to my mission for The Ask so you can bet, we had a lot to say!
Watch “Should personality impact your business decisions” and hear…
Advice on using your personality as both a filter and a positioning strategy when making big business decisions
Why matching your business operations to your personality could be the key to success (and how Jessica’s corporate planning days and her Taurus Moon sign has dictated her own methods)
How to know if you’re a “dreamer,” “integrator,” or “doer” in your business—and why that matters for scaling
How we both use our strengths (and the help of trusted team members) to balance structure, serendipity, and sustainability in business
Jessica Lackey & Ellen Donnelly ask "Should your personality influence your business decisions?”
… back to the interview…
Jessica Lackey’s journey to building an aligned business, and her slow pivot.
Have you ever felt like your business is running just fine on paper, or at least to the outside world, but deep down, something just isn’t clicking? Jessica Lackey has. After building a business as a fractional COO—supporting companies with $750k–$2M in revenue—she realised that wasn’t the work that truly lit her up.
So she pivoted. Except, this wasn’t an overnight switch up. Jessica, true to her personality, moved through the pivot in a methodical fashion and built up the reserves, brand reputation and client base brick by brick.
Her pivot is packed with lessons for you if you are also questioning your current business model.
What were the signs that you needed to make a change?
Whilst running her fractional COO business Jessica spent her days creating budgets, managing team task boards, and running prioritisation meetings. While she enjoyed some aspects of this work—like crafting business models and diving into financial strategy—she found herself drained by the maintenance tasks. The real spark came when she started teaching.
“I realised my best days were the ones where I was codifying what I’d learned into frameworks and seeing the light bulbs go off for others,” she told me. “That’s when I knew I wanted more good days like that.”
How did you make the decision to pivot?
Jessica’s pivot didn’t happen overnight. It started with small steps: hosting free monthly workshops to test her love for teaching and sharing knowledge. The response was overwhelmingly positive, with attendees praising her ability to make complex business concepts approachable and actionable. This feedback confirmed her gut instinct—that there was a gap in the market for foundational business-building skills for her particular audience: expertise-based entrepreneurs.
“Once I realised teaching was the model I wanted, I knew the steps I needed to take,” she said. “It took two years to build the foundations for that model, but it was worth it.”
How did you discover your ‘zone of genius’?
Understanding that she was not in her ‘Zone of Genius’ enabled Jessica to recognise she was in stuck in a cycle of tasks that relied on her depth of skillset, except, did not energise her. Tasks like pulling reports, maintaining systems, and managing long-term operational workflows. While she loved the creative aspects of setting up business structures, the ongoing maintenance projects had her feeling disconnected from her work.
Her insight? “I needed to build a business that focused on what I’m best at—creation and teaching—and leave the rest behind.”
That’s what it looks like to build a business around yourself — you can follow your energy.
Where are you in the pivot process now?
After two years of restructuring her business, today Jessica runs a teaching-focused business model divided into two key offerings:
Defining Foundations: For early-stage entrepreneurs building the basics.
Refining Foundations: For those ready to level up their strategies and skills.
Next, Jessica plans to codify her one-on-one services into scalable courses, challenges, and templates. “I want to serve more people without losing the personal touch,” she told me
What sacrifices have you made to make this change possible?
Jessica told me honestly that building her teaching curriculum took nights and weekends, and the pivot didn’t immediately increase her income. “I traded short-term revenue growth for a business that feels sustainable and aligned with who I am,” she shared.
What advice do you have for anyone going through a pivot?
Jessica’s advice is grounded in her own hard-won lessons:
Plan for the pivot. “A real pivot requires time and cash—be honest about your revenue and expenses.”
Be really clear about your revenue and expense model. “Not all models are created equal. Build one that works for you, don’t chase someone else’s business mode
Stay in touch with Jessica
You can sign up to Jessica’s newsletter, read her blog post about finding the right business model for you and her business model mini-class, and connect on LinkedIn.
I loved hearing the truth behind Jessica’s journey, which serves as a powerful reminder that you don’t have to settle for a business that feels out of sync with your strengths.
I know from my experiences as a certified coach to hundreds of clients… this level of personal growth and inner reflection takes work. To get clear on what drains you, excites you, and what your ideal business looks like. I also know that if you do the work, and take action on your findings, that you can build something not just profitable, but deeply meaningful.
Because not all business models are created equal — the best ones, are built around you.
So if you’d like support with your own pivot or next bold move in business…
Check out some of what’s on offer from me, Ellen, business coach for founders ready to evolve:
For Londoners: Join me at this IRL event in collab with Pivot Club, from Women On Our Way - grab tickets for the on 3rd December
Download a 3,700 word guide I’ve written for you — if you think something might be off in your business and want help to figure out the right next step
For more hands-on support check out my 1-1 coaching programme High Expectations designed for seasoned entrepreneurs exploring their next phase in business book a call or email me.