Iesha Small

writing, career pivots, side hustles

Build you career like an entrepreneur.

How I spent 5 months without a job

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


I resigned my job with nothing lined up. Here’s what I did for 5 months

I resigned my role with nothing lined up. My last working day was in July 2023 and every now and again the small group of people I told would ask how my job hunt was going.

The truth was I actually didn’t want another job.

I wanted to rest and chill and recover from being burnt out. And I wanted to do that for as long as I could make our savings last.

I decided to treat it as a sabbatical. Eventually it will have lasted 5 months from Aug – Dec and here’s what I’ve been doing.

1. One month off chilling with my family 

2. Had somatic therapy 

3. Had some career coaching 

4. Took a family holiday  

5. Decided to write publicly every weekday on LinkedIn

6. Half-heartedly applied for some jobs because I thought should 

7. Visited Lisbon for the first time with partner

8. Spent time with an ill family member 

9. Spent time with friends 

10. Spent time with people I respected to help me figure out next steps 

11. Journalled A LOT 

12. Stopped applying for bulls@%% jobs I didn’t really want 

13. Improved my mace swinging skills 

14. Attended a couple of steel mace workshops 

15. Met some new and interesting people 

16. Asked contacts for introductions to interesting people 

17. Binge watched The Last of Us 

18. Had some new experiences 

19. Had various meltdowns about not having another job. 

20. Went on long solo walks 

21. Examined my relationship with failure and success and self worth 

22.Developed a new talk on Social Mobility 

23. Cooked and hosted my first ever BBQ

24. Listened to a lot of podcasts 

25. Listened to a lot of youtube videos

26.Ignored my bank account

27. Did roast for the kids most Tuesdays 

28. Learnt how to spin a sword 

29. Generated income as a consultant 

30. Attended writing group in my dressing gown several times 

31. Attended a nature writing workshop

32. Went on a bat walk

33. Invested last bit of savings on developing business skills.

34.Obsessively checked my bank account 

35. Got offered a job.


I wrote an earlier version of this post on LinkedIn a couple of weeks ago in early November. I was scared to post it because I thought it made me sound like a failure. I decided to do it anyway as I thought it might be interesting for anybody else in a similar situation. Surprisingly to me, I had an overwhelmingly response and many people, including a decent number of senior leaders and CEOs told me in private that they found it inspiring. So there’s a lesson in there somewhere!


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How I spent 5 months without a job