Iesha Small

writing, career pivots, side hustles

Build you career like an entrepreneur.


Hi, I’m Iesha.

Thanks for dropping by.


I have to be honest with you, I need to update my website. It’s on the list of things to do but in the meantime here’s a

Quick Summary

I’m a communications professional building my own business alongside my day job.


I help leaders (and geeks) career pivot, confidently create the lives and careers they want and build profitable passion projects.


Engineer → Assistant headteacher →Head of Comms


I write every weekday on LinkedIn and I have a weekly newsletter. Sign up above. 

Want a bit more info?

Ok here we go…

I trained as a mechanical engineer. A year into my first job I realised it wasn’t for me. I retrained as maths teacher. I was promoted relatively quickly and became a senior leader. High stress led to a breakdown. The therapy I had while signed off uncovered my hidden creativity.


Photography started as a hobby to document and make sense of the world. It quietened my internal gremlins. Sharing my work online led to writing a book, The Unexpected Leader, appearing several times on the BBC, writing for The Guardian and speaking at the National Theatre.

Pivot 1

Along the way I became a self-taught marketer, podcaster, documentary director  and policy geek. I attracted personal consulting, writing and speaking opportunities in the education, creative and non-profit sectors. I also  created new innovative  revenue streams  for the social enterprise I worked for.

Pivot 2

After leaving teaching,  I influenced national policy and learnt to build strategic networks to create change for vulnerable young people.


Covid lockdown, bereavement and grief burnt me out. I quit my job with no idea what to do next. I started writing every weekday on LinkedIn to give structure to my days.

Pivot 3

After 3 months I applied for a job.  While I was in Lisbon waiting to be contacted, I knew I hadn’t got it. I decided it was time to stop dabbling. No more sporadic consulting and waiting to be picked. I was going to start the proper business  I’d been meaning to for years. Cute Fruit Ltd was born.


After 3 more months I’d written multiple posts on LinkedIn that led to direct sales. I’ve had individual post with 5x and 25x reach and lead to sales. All with under 2000 followers.


Attracting attention, marketing and selling online services  under my own name  transformed what I thought I knew about communications.


Now I use what I’m learning in my side hustle to inform my Head of Communications role – I got the job after all!

How I can help you, now

I share my learning about career pivots, building a small online  business, communicating online and  leadership. I share through my personal lens as an introvert from a working class background. I’m transparent so I can help others and save them time.


I offer online workshops, 1:1 career strategy sessions and the 6 month Career Pivot Pro course, email to find out more.

Other links

For examples of my commissioned writing, broadcasting and corporate storytelling  click here


If you want to know a more detailed career history  check out my LinkedIn I write there every weekday.


To have me arrive in your inbox most weeks  subscribe to my newsletter 


You can contact me or find out more about working with me via my email address at the bottom of this page.

Iesha Small, in purple top and pink trousers, delivering a speech at a conference.