Line Manager Update #3

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 a week full of surprises; money is getting tighter; my generosity around coaching content is significantly reduced; exercising more and first steps taken to change diet; I seem to be gravitating towards arts organisations – not entirely sure whether that’s necessarily a good thing in terms of sustainability.


  • ‘moving towards’ is much better than ‘moving away from’
  • being goal oriented can stifle serendipity and client-driven agendas
  • contrary to a life of thinking otherwise, compliments are valuable
  • don’t compare; seek out difference; celebrate it
  • fledgling ideas are enriched in the company of others
  • develop ideas by testing and re-testing; no idea is right first time
  • once you’ve identified the unwanted weed in the garden, get rid of it quickly
  • corporate environments demand more energy
  • there are a significant number of people around who are basically crap
  • organisational politics are the enemy of a nimble hungry freelancer; avoid


  • commissioned to write an article – massively pleased/proud
  • came up with three pitches for article – third one was the most interesting
  • met up with 5 energetic individuals I admire who’s perspective helped shape mine
  • unexpected work offer for a short-term project over the next few weeks
  • successes have made me consider offering other services 
  • setting up a monetising platform for pay-per-view coaching content 
  • cycled 50 miles in one week 
  • drastically cut down on wine
  • published Leeds Piano Competition podcast – the best performing podcast yet
  • valuable CPD session this week 

Things to change

  • spend a bit time before each task focusing on why you’re doing X
  • is now really the right time to be doing X? 
  • can you achieve X in half an hour? 
  • plan content more 
  • coaching insights are no longer free 

Next week

  • one CD review, one interview, and a podcast clip
  • nail solid goals and see them through to completion in 30 minute blocks
  • identify out of town arts orgs and categorise NPOs
  • set up a new email subscription service because of stupid GDPR

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.

Line Manager Catch-Up #1

For a few weeks now I’ve posted Line Manager Updates on my Facebook page – a way of consolidating in my own mind what’s going on in my new life and, I hope, sharing that with other people who might be going through a similar experience.

This week I’m posting here on the blog – it feels like its natural home. 

Essentially, this is an accountability tool. It’s an opportunity for those of us who work in relative isolation to document successes, commit to future goals, and explore challenges and issues. Essentially, a coaching exercise (kind of).

And because it’s important to be concise I’ve included a list of things under five headlines: insights; highlights; successes; things to change; and, next week. 


  • Not every freelancer you meet is going freelance for the same reasons you are; not everyone is in the same ‘place’ you are mentally.
  • Some people move from freelance life to PAYE because they reach a point where they need structure in their life. The coaching question to remember here is what is the thing you need right now? And what is the thing the most important person in your life thinks you need right now? 
  • Be vigilant of thinking catastrophically. Such thinking patterns can crop up in unexpected places and times, and in varying degrees.
  • Thoughts and feelings influence the quality of your actions in ways you probably don’t even realise.
  • Just because some stands up and speaks about their successes running a business doesn’t mean they are the authoritative source on the subject.
  • Freelancers compare themselves to one another without even realising it. Comparing yourself to someone else is a dangerous dangerous thing.
  • Busy-ness doesn’t mean success now, just like busy-ness meant fuck all in the corporate world. Resist saying you’re busy. There’s a blog post in that.
  • Being a freelancer doesn’t mean waiting for the phone to ring. It means deciding on who you want to work with. There’s a blog post in that too.
  • Don’t underestimate the power of snatched conversations with people. If you engage fully unexpected consequences can emerge – new ideas/ renewed impetus.
  • You’re wrong about the stuff you think you’ve been running away from. You’re actually running towards something. That means – quite unexpectedly – you’re a broadly positive indivudal (very NLP).  


Research completed on Twitter and Facebook. I know the audience better now. Every person on the list could potentially stimulate future ideas. I like that idea. 

Various meetings this week. But one with [NAME REDACTED] was incredibly invigorating. An amazing woman. We’ve known of one another for years but never spent any time together. An hour in her company confirmed what all of my journalist contacts have said to me. She is an amazing force. Infectious energy. The kind of people I love being around.

Recorded three podcasts this week. I adore the process from beginning to end. I want to do more.

M’s top tip re: Line Manager Updates. Who is the character of the line manager exactly? Who would I want my line manager to be? Who would be the worst line manager (easy one), who would push me? How do I need to be pushed to deliver more? How would I reflect that in future updates?

K’s top tip re: securing future coaching work – build case studies, sell impact.

H’s (and J’s) top tip re: securing future engagements – referrals and testimonials.


  • Meetings confirmed for the next couple of weeks.
  • New ideas for future blog posts and articles.
  • Dates for future training course confirmed. 
  • Training packages drafted. 
  • Potential customer base ‘identified’ – needs fleshing out. 
  • Blog posts consistently doing well. 

Things To Change

  • Recognise when you’re tired. Stop. Do something completely different.
  • Devote entire days to one part of your business. Shut down at 5.30pm.
  • On no account watch other freelancer vlogs.

Next Week

  • Complete lists of contacts on Twitter.
  • Complete business model canvas.
  • Edit two podcasts; line up six more podcasts.
  • Draft editorial for new ‘secret’ podcast series.
  • Five classical music blog posts (two reviews); four coaching posts.
  • Complete documentation for four products.
  • Identify platforms to write for. Pitch?
  • Dedicate a day to reading about coaching

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.

Planning out the month ahead

Because charts bring order to chaos. And hand-drawn charts add a hint of perilous vulnerability. 

I’m a recent convert to bullet journalling. If you’re not aware of it already and you’re a lover of a notebooks then be sure to take a look at this video.

Every month, I draw out charts for the month ahead – a mini goal-setting exercise with a pseudo-graph to capture how my mood fluctuates throughout a four-week period.

At the end of the month I look back on it all and see what’s occurred and what hasn’t. I confess I find the process fun. 

Have May on me

I’ve included May’s blank charts in this post both as JPGs and a PDF download (see bottom of post) in case you want to use them. If you do, I’d be interested in your feedback (please leave in the comments section below). 

How to use the charts

A word about the quality of these: they’re hand-drawn because I like hand-drawn stuff. They’re prototypes. In the future I’m thinking I’d charge for them. But May you can have for free. 

Tracking mood isn’t done because there’s a perceived problem that needs correcting. Instead, its just an opportunity to track what’s going on. Sometimes important things get overlooked in the everyday. 

The mood chart (above) doubles up as a productivity chart too. In fact, you can plot as many lines as you want on it (just use a different colour for whatever it is you want to plot).

For mood, I monitor what my mood is as a score out of ten, three times a day (the process is not as onerous as it sounds – just programme your phone to remind you). I join the dots up at the end of each day – I derive an inordinate amount of joy doing this. Do the same for any other ‘thing’ you want to monitor each month. Take a look at what I’ve tracked for April (NB there were some low-points).

You need to complete the Goals, Needs, and Intent page (above) at the beginning of the month. It’s not really a to-do list, more an list of aspirations. I usually fill it in and then forget about it for the month. At the end of the month, I take a look at it to see how I’ve done. I’m normally surprised by the extent of my own productivity.

How you fill the chart in is down to you. But, if you’re looking for pointers, here’s how I do it: I categorise the areas of my professional and personal life in eight sections (for me that means coaching, blogging, video, podcast, training, home stuff, reading, pals).

In the columns underneath I write the specific goals I want to complete by the end of the month in relation to each subject. I try to keep each reference to no more than three words (this stops me from being verbose).

In the row underneath, I decide on one thing I need in order to complete on the corresponding goal above. Underneath that, one word for the intent I need to adopt (this is usually the most difficult part of the process – intent can be a little more difficult to determine).

Happy planning, etc. 

Download a prototype PDF for the monthly tracker. Please share any feedback you’d like to share to improve the usability of the chart in the comments field below.

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.

Business not Playtime

I used to think of myself as a freelancer.

Now I realise I was wrong about that.

I have a theory. Or an insight. I don’t know which it is. But its interesting. 

First off, there’s a big difference between the what you deliver and the way you sell it. Just because you know how to bake a cake doesn’t mean you know how to get some to pay for a slice. 

Similarly, there’s a big difference between coaching and sales. In order for this all to stand a chance of success, I need to be able to do sales as well as I’m able to do coaching.

The link between coaching and sales

Coaching is all about the individual setting the agenda.

As coach I listen and react, feedback and challenge. That’s what you’re paying for. I bring my knowledge, experience, and attentiveness to our unique relationship in order that you can be a better version of your present self.

But before we can get to that actually doing stage – the coaching – I need to be able to convince you  (the customer), or the person with the budget (the sponsor), that this product you’ve never experienced before and don’t realise you need (the coaching), is best delivered by me (who you may well have never heard of before).

Before we get to the coaching stage, it’s sales. Both are entirely different skill sets, though in the Venn Diagram that features both, there is a sweet spot in the middle – conversation.

Labels are (unexpectedly) important here

Bigger than that, is what we label all of this.

This thing that I’m doing is not ‘going freelance’. That phrase doesn’t cut it. It’s not just going ‘self-employed’. That doesn’t cut it either.

It’s setting up your own business.

That phrase is terrifying because it’s grown up. It’s sensible. It’s all or nothing. It is the biggest kind of risk. Personal risk. Reputation.

Connotations with the word ‘business’

There are a multitude of connotations with the word ‘business’ – a much-bandied around word. Pervasive. Loaded. Assumptions emerge from it like an invisible gas, one that makes us go a little light-headed and results in all sorts of unhelpful beliefs.

  1. All businesses are well-oiled machines, well-planned, successful things
  2. All businesses are staffed by people who wear suits (women and men)
  3. All businesses run at a profit
  4. Only grown-ups can run businesses
  5. A business must be underpinned by a rags to riches story
  6. Businesses are not for the faint-hearted
  7. You must be thick-skinned to run a business
  8. You must be pushy, uncompromising and ruthless
  9. You must be able to come up with a cast-iron idea quickly
  10. People must be captivated by you and everything you say

I could go on. I won’t.

I frequently think this stuff. It is noise. It is a form of self-doubt, I suspect. Or if its not as severe as that, it’s a monologue that distracts from the necessary thinking and doing required for getting work from people who don’t realise the extent to which their lives could be transformed if they hired you.

It’s as these points in time I have to remind myself what exactly a business is to me. It’s a way of selling the services that I do best, in order to get money to buy me the freedom that in turn helps me perform at my best.

What’s helping you and what isn’t?

But I also have to interrogate what other beliefs I’ve got about what I’m doing at this moment in time and assess what’s useful and what isn’t in pursuit of the end goal.

Picture the scene: a struggling writer with nothing but an old typewriter to bash out ideas, surrounded by previous attempts screwed up in tight balls of misadventure and increasing bitterness.

When I write (when others I know who write better than me reveal some of their process), I’m always trying and failing and trying again, driven by an insatiable need to make it work.

So I need to think of this new life as me setting up a business. That process demands melearning new skills (often deploying them ‘on the fly’), at the same time as maintaining a forensic level of self-awareness and self-regulation.

It is punishing. There’s no-one you can piss and moan to. No-one you can really delegate to either (unless you’ve got a never-ending source of capital to invest). You can either do this, or you can choose not to do this.

This is business. It’s a simple as that.

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.