From Setbacks to Success: Leadership Lessons from the Entrepreneurial Journey
I’m just launching Jo Blakeley Training, and I am setting a positive intention that it will be an overnight success. You know, the kind of overnight success that takes 20 years, countless failures, and a truckload of resilience.
It got me thinking: most people don’t see the trial and error, setbacks, and sheer determination behind any success story. To get here, I’ve set up not one, not two, but three different businesses (not including Orchard Training, which would make it four). And while none of them were “failures” as such, they taught me valuable lessons—especially about leadership in the workplace.
Lesson #1: The Right Timing and Team Matter More Than a Great Idea
My first venture, Life Infusion, was something I thought I always wanted to do—an intensive five-day retreat to help people transform their minds and bodies. I covered confidence and self-esteem training and coaching, a business partner (my personal trainer husband) handled fitness training, and a third partner led nutritional courses. It took six months to set up—branding, marketing, website, the works—before we even ran the pilot.
The problem? While we got along as friends, only two of us clicked as business partners (you’ll be pleased to know that it was me and my husband!). And I realised that setting up a brand-new—highly intensive—project with a nine-month-old in tow who thought sleep was optional wasn’t my wisest decision. The result? I was exhausted, couldn’t give my best to clients, and I realised I didn’t actually like running retreats. A dream had been shattered. We ended up dissolving the business after the pilot.
Leadership Takeaway: Timing is everything. Don’t start a business—or any major workplace initiative—when you’re already stretched too thin. Also, test the working dynamics of a team before investing in branding, marketing, and websites. A pilot isn’t just about testing the idea; it’s about testing the people involved. Finally, what you think you want might turn out to be very different when you actually do it. But at least I tried and won’t be left wondering ‘what if.’
Lesson #2: Adaptability is Crucial
Next came Fittogether UK, this time my husband and I teamed up with a different nutritionist. The concept was similar—helping people improve their physical health and mental well-being—but this time, we focused on local courses, coaching, and exercise classes.
Why didn’t it work? We quickly realised that our model wasn’t financially sustainable. What we needed to earn simply wasn’t feasible to charge clients. With hindsight, it would have been a fantastic digital offering—an app, virtual classes—but we were too ahead of our time. The technology wasn’t there yet.
Leadership Takeaway: Adaptability is crucial. Sometimes, great ideas fail simply because the environment isn’t ready. Leaders must be willing to pivot, reassess, and recognise when a model isn’t working. Timing and technology can make or break a venture.
Lesson #3: Know Your Market Before Investing Too Much
Then came The Bliss Expert. My corporate training courses often led to delegates asking if I offered anything for individuals. So, I thought—why not? While writing my first fiction book (Blokes, Beers & Burritos), I set up courses for individuals, thinking it would be a perfect complement.
The first course had five attendees. The second had four (I thought the numbers were supposed to go up, not down!). It became clear—back then—that while people love the idea of self-improvement, many prefer a quick fix rather than putting in the time and effort themselves. I realised that my passion for personal development was best channelled through workplace training.
Leadership Takeaway: Knowing your audience is everything. In business—and leadership—you need to understand what people actually want, not just what you think they need. Market research is essential before committing time and resources.
The Next Chapter
And now? I’ve put all my learning into my latest venture: Jo Blakeley Training, which explains why my tagline is a personal approach to professional growth. I’ve spent the last two years researching and updating all my courses with the latest in neuroscience and psychology, written a non-fiction book, and designed my first online course.
I’ve already learned that going from concept to reality takes a lot longer than expected (two years, to be precise!). I’ve also discovered that you need to be a jack-of-all-trades—graphic designer, lighting engineer, and editing whizz. All while juggling a day job and parenting a teenager. (And to think, I thought babies were tough!)
So… I can’t wait to be asked, “What’s it like to be an overnight success?”
And if—worst case scenario—it doesn’t work? Well, I guess I’ll have another learning opportunity to add to the list!
Final Leadership Thought
Success—whether in business or the workplace—is never instant. It’s built on persistence, learning from failure, and adapting to new challenges. The best leaders embrace the journey, laugh at the setbacks, and keep moving forward.
So, what’s your “overnight success”?
Acknowledgment: This blog post was written by me: Jo Blakeley. While I used AI assistance (ChatGPT) for refining grammar and presentation, all ideas, insights, and content are my own.