The Tortoise Wins: Lessons Learned From a Year of Starting Over
After a year of starting my business from scratch, I’ve learned that progress isn’t always about speed. From burnout to breakthroughs, here are 9 lessons to help you navigate your journey.
I hope you had a good summer and found some time to relax. It’s now been over a year since I left the Abram Wilson charity and began my journey of starting from scratch (again!). After a bit of reflection, I thought I’d share the top 9 lessons I’ve learned from building a new business over the last 12 months. If you’re thinking about quitting your job, changing your career, or starting something new, this one’s for you.
1. Before Starting Again, Take a Break
I made the mistake of not planning a proper break after leaving the Abram Wilson charity. Instead, I kept pushing forward, as we're often conditioned to do. But after 11 years in the same job, I felt lost. I should have created space to let ideas form naturally. One of my teachers called this the "fertile void"—doing nothing until clarity emerges. I didn’t do that, and it was a mistake.
2. You Don’t Need to Know Exactly What You’re Doing
Another mistake was feeling I had to announce my next move before I'd even left the Abram Wilson charity. A lot of judgment comes with making changes in your life, and I wanted to dispel people's fears that I'd made the wrong choice by coming across like I knew what I was doing when I didn't, not really. I rushed into a mission that mirrored my previous work, which wasn’t quite right. I’ve since learned it’s better to start without a fully formed plan. If people ask, which they will, be honest and say you don't know yet.
3. Don’t Niche Too Early
I pivoted from my first mission to a new focus inspired by my book, Becoming Brave. I decided I was going to create a company called Becoming Brave Co and a signature trademarked programme called BRAVE aimed at people who had experienced loss and wanted to be braver. But trying to niche early just served to stifle my creativity and moved me backwards toward grief instead of forward to something new. It’s okay to keep things broad at the beginning.
4. Pushing Too Hard Can Backfire
In the first few months, I pushed myself too hard, which led to two mental health dips. My body went into shutdown mode, and I felt hopeless and like a failure: what was the point of my life anyway? After the second episode, I knew I had to slow down and approach things differently.
5. Quiet Time Brings Clarity
To recover, I created a retreat at home—no social media, strict wellbeing routines, and a healthy diet. After about a week, I started to feel more grounded and clearer on what I needed to do next.
6. Leverage Your Network
Once I regained some clarity, I contacted everyone in my network with personalised emails (thank you, Yet Another Mail Merge). It took weeks to set up, but it led to 50-60 calls, helpful advice, introductions, and paid work. The value of connecting with people cannot be overstated, and I even ended up creating a 90-minute online workshop about this very approach for one of my clients.
7. Experiment Freely
I gave myself permission to experiment. From February to July, I explored different ideas. However, even though I knew was experimenting I still couldn’t bear not having an answer when people asked me what I did so I created a third new mission and niche focused on coaching and mentoring stretched and overwhelmed creatives. The problem with this was it didn’t encompass all the other things I was doing: designing bespoke workshops that were fun, dynamic, and playful to achieve serious outcomes; helping primary school children connect with their feelings; and providing fundraising and strategic support. This all led me to...
8. Reflect and Rest
By July, I had a clearer picture of what I enjoyed doing, was good at and could make money from. I created a six-page business plan to guide my next steps. Then, I took the time off I should’ve taken a year earlier, spending quality time with my partner Adam and his son, which was busy but lovely.
9. Be the Tortoise
I’ve returned with more confidence, realising that for me, slow and steady wins the race. Trying to go 100 miles an hour might benefit you in the short term, but it's not sustainable. By going slower, I can create space for ideas and clarity and am much less likely to burnout. It’s hard when everyone around you seems to be screaming 'Go! Go! Go!', but taking things at your own pace is essential.
A year on, I’m back with a new mission—achieving serious outcomes playfully, with no niche. You can read more about what I'm focusing on below or head to my website at jenniecashman.com.
If September has hit you with a “WTF?” feeling, you’re not alone! Give yourself permission to progress in a way that feels right for you, find your rhythm, and avoid burnout.
My question for you is: What could you let go of or push back to help you slow down and create more space?
Till soon!
Jennie x
P.S. Here are some ways you can work with me:
Organisations: For organisations seeking new and creative ways to engage their teams.
Brian Sutton-Smith said, “the opposite of play isn’t work, it’s depression.” Play is often seen as the opposite of productivity, but what if it could help your team become more productive, engaged, communicative, trusting, and innovative?
I offer bespoke playful facilitation, creative coaching, and support with wellbeing, fundraising, and strategy. If you're open to trying something more playful, [click HERE to find out more].
Individuals: For purpose-driven creative entrepreneurs feeling stretched and overwhelmed.
Are you juggling too many ideas and projects? Need clarity and confidence to grow your career or business sustainably? Want to slow down, connect with your body, and get clear on long-term goals? I can help you create a two-year plan to make more money, find balance, and prioritise what matters to you.
If this sounds like you, [click HERE to find out more].
Primary Education: For educators working with Reception – Year 3 to strengthen pastoral care and enhance PSHE curriculum.
My sensitive, engaging assembly and workshops for 4-8 year olds combine storytelling, drama, and emotional intelligence to explore courage and fear while normalising loss in an age-appropriate way. The workshops accompany my Guardian-reviewed children’s book Becoming Brave.
If you’d like to book an assembly and workshop, [click HERE to find out more].