Line Manager Catch-Up #2

I’m writing a weekly post in a series of ‘Line Manager Updates’. It’s a way of consolidating in my own mind what’s going on in my new freelance life. In the process I’m hoping that the stuff I stumble on helps other people who might be going through a similar experience.

In this update, more insights, successes, and things to change.

Top line: it’s been tough, but it feels like the product is bottomed out. The unique sales process feels a whole lot more familiar. Pitching isn’t weird anymore.


  • Difference between a daydream and a goal: the former is the foundation for the latter.  
  • Working for yourself doesn’t mean working alone. You might need partners.
  • There is an industry dedicated to supporting fledgling businesses – a distraction. 
  • Am I working hard enough? I’d prefer to ask ‘am I thinking smart enough?’
  • Be patient. Your thinking develops at the pace that suits you. Strive for authenticity.
  • Selling coaching requires stamina and patience. 
  • Those who consider coaching as ‘pop psychology’ aren’t ready for coaching. 
  • Show respect at meetings by making things run-to-time. 
  • Meeting others challenges your own perspectives and helps develop your thinking. 
  • Don’t let hope for something in the future distract you from the task at hand. 
  • If something doesn’t happen then the chances are you’ve dodged a bullet
  • What’s in your circle or concern and what’s in your circle of influence?
  • What’s in reach? What’s just out of reach? What do you need to stretch for?  
  • Writing about difficult subjects is powerful and authentic. Don’t be deterred. 

Seeing ‘The Ex’


  • Two full days of contact research; one meeting and one introduction secured in 24 hours
  • Business Model Canvas exercise reinforces confidence, legitimising process
  • Value Proposition exercise fuels motivation and self-belief
  • Three new coaching products and packages drawn up
  • Developed a service distribution strategy 
  • Updated website ‘About‘ page. 
  • Case study / proof of concept offers made 
  • Visited ‘The Ex’. Didn’t pine. Felt uncomfortable at the way people were hemmed in. 
  • Stumbled on a digital publishing idea I had a few months but had forgotten about. 

Things to Change

  • Meet more – face to face conversations fuel fledgling relationships
  • Devote hour-long blocks to specific tasks. Drive harder. Complete. 
  • Email more
  • Read more 
  • Tighten up the coaching explanation, and the pitch

Next Week

  • Build more Twitter lists
  • Flesh out the digital publication idea for entrepreneurial scheme
  • Clip up podcast and subtitle
  • Publish next podcast
  • Research out-of-London arts organisations
  • Investigate digital production jobs (just in case)
  • Follow-up on podcasting leads
  • Coaching associate meetings
  • Tighten up the pitch and the primer

Jon Jacob is an ICF accredited leadership coach, mentor and team facilitator. Find out more about his professional background on LinkedIn.

Email him at or call him on 07768 864655.

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