One year on

It’s been a year since I went freelance working as a freelance journalist and digital producer, PR, and executive coach.

It has been an exhilarating and often demanding experience. I wanted to document this personally important anniversary with a few insights.

They’ll cover the range of activities I’m engaged in and the worlds I occupy – classical music, coaching, digital and freelance life, for example.

I’m hoping it will give you a flavour of what’s going on and how my thinking has changed .

How I marked the transition point has changed

I used to say, “I left the BBC in July 2017. “

Now I say, “I went freelance in July 2017.”

The difference between the two statements is important.  I used to define myself by the organisation I work for. I can’t do that anymore, obviously. But, more importantly, I feel like a far more complete (and therefore confident) individual by defining the point in time when I embarked on a new period in my professional life.

I’m doing the same work but for different people

Nothing has really changed in my day-to-day activities. I’m doing much the same work, on my own terms, for a range of different clients. 

Most of my work has come through referrals

I’m still not sure whether this is a good thing or a bad thing. High expectations of myself dictate that I would like the percentage share of self-generated versus referrals to be 70/30. At the moment, it’s the other way around.

My assumption is that there’s only so long before the generosity of others will run out. Inevitably, I’m saying that from a fundamentally self-critical stance which is both a strength and, at times, a weakness. 

Freelance life is perfect for self-regulation

With no one else to compare yourself to in your day to day work you quickly come to accept what your strengths are. You challenge yourself more frequently and harder. Energy levels are higher. Self-awareness increases. 

You learn at your own pace

There are endless books on going freelance. Quite frankly, the only way to learn how to do it is to actually do it. That means you’re learning day to day. And for us auto-didacts that’s just peachy. 

Coaching business is phenomenally difficult to sell

There is a conflict between the kind of person you have to be in order to sell-in coaching services to an organisation versus the kind of person you are when you’re running a coaching session.

Having to occupy both those ‘personalities’ means one or either suffers in terms of authenticity and integrity. I don’t think you can successfully do sales and not risk your authenticity as a coach (not everyone will agree with me here – and that’s OK).

I’d rather be a good coach than a good sales-person, even though I acknowledge I need to be an effective sales-person in order to continue my coaching work. 

Coaching is (often) leveraged by those who know little about coaching

People assume results can be guaranteed (and some coaches promise results too). In that way coaching is weaponised by HR staff who use the methodology to implement radical change.

Many HR people I have spoken to hold this regard for coaching services as a badge of honour – an element of their armoury that proves they are good at their HR work.

Some other commissioners of services have claimed expertise in coaching services based on their 8-day intensive training programme (mine consisted of something in the region of 25 training days, two one-to-one coaching programmes, plus individual study and reflection).

Coaching is something which is bestowed on individuals

One person I spoke to regarded one-to-one coaching as a ‘luxury’ reserved only for the most senior of individuals. One company executive made clear to me that if any one of this senior staff sought a budget in order to develop themselves in their day-to-day work then this would undoubtedly be looked upon as an admission of weakness by him and his HR department.

One chief executive of a mid-size organisation in the arts sector explained that he was disinterested in giving his middle and junior members of staff coaching to develop their thinking because, ‘they’re on a low wage, and really they’re not going to earn any more with me nor elsewhere in the sector, so what would be the point in developing them?’

I’m skeptical about coaching as a primary source of income

I am still a passionate advocate of the coaching process and will still pursue coaching opportunities, but the misinformation that abounds in mid to large scale organisations encourages me to actively seek out individuals I would like to coach, instead of looking to associate networks for sources of coaching work.

This method means I end up working with the people who get the best from me in the best scenarios – a much ‘cleaner’ experience for all. 

I also worry that if I could only do coaching and I did, then I’d become a bit of a coaching bore. That’s assuming I haven’t already become one. 

Classical music and the arts is where I feel most at home

The transition from corporate communications and PR to classical music has been instinctive. It’s also something which I did set out to do, although didn’t necessarily have a strategy in place when I set out on this path in July 2017. I feel most at home in this world and see opportunities to support, develop, and in some cases innovate in the sector.

That I’m not paid full-time to do that is, I’ll be honest, a bit of a head-fuck. But one year on I notice that things are gaining momentum – the legwork is paying off in unusual and gratifying ways. A few commissions, one or two project pitches accepted, festival invitations, and even an invitation to present a classical music event in a few weeks time. There are also new content ideas for 2018/2019 emerging. 

(Let’s revisit this one next year and see if I still feel the same way.)

People won’t pay for content, so think of the content in a different way

The very thing that drives bloggers, exercises them, and stimulates the endlessly dull naval-gazing about their validity – how to monetise content for the small-scale content producer – is both a headache and an opportunity.

First up is that its worth stressing that the blog is supported by generous doners whose money helps meet costs. When I talk about monetising content, I’m talking about getting money for the time you put into it. 

The answer has been to look at the blog from a different perspective: I’m producing online content to raise awareness of my skillset so that others will consider me for any paid work they’ve got coming up.

In my case, the blog and the podcast has provided a great way to get in front of people. Each interaction stimulates thought which fuels ideas. Some of those ideas fly. Some of them don’t. The point is you have to pursue those ideas for their life cycle. The blog and the podcast is the beginning of a idea’s development path in that way.

So, thinking in terms of ‘I should be getting paid for this content I’m making on the blog’ is counter-productive. You’ve got to be in it for the long game. 

People also won’t pay for content production

This isn’t right across the board by any means, but there does seem to be an assumption that content production doesn’t really cost time. So therefore, some people will quite happily ask for content to be made and then express surprise when I ask what budget they have available for it.

The value of marketing content (especially digital) is difficult to value. And because everyone knows that in theory they could and probably do produce their own kind of content for Facebook or Twitter, then the idea of paying someone else to do it leaves them feeling like they’re being exploited by a greedy content producer. 

Variety is key to creativity

I am basically doing the same work I was doing two years ago – just for different people. I’m also doing a range of work for different organisations. That variety of activity is crucial to keeping me energised. And that benefits the client because that means they get the benefit of a suitably energised and creative mind. 

It takes far longer than anyone says it will take

Many people who have asked how the past year has been going have commented on how much further down the line they think I am compared to others they know or, in the case of other freelancers, their own experience. That’s reassuring.

At the same time, I know of people who have been running their own business for five or ten years and confirm that its only now that things have taken off. I recognise I’m impatient, hungry, and ambitious. That’s useful for motivation. At the same time it can be quite restrictive (especially when things don’t move fast enough).

Spending a year earning the bottom line is healthy

I set out to clear my debts and earn the bottom line this past year. It has been demanding and sometimes been annoying. But, its helped me appreciate that I’m a good deal more frugal than I previously realised, that public transport costs are stupidly high (even with a daily cap), and helped me recognise what I’m worth. I don’t I ever really appreciated any of that when I was PAYE. 

It’s far from easy but it suits my preference

I spent years believing that permanency was the goal – that validation could be achieved with a security ID and years of continued service in an organisation. The flipside of that is the destructive nature some large-scale organisations can have on the psyche.

If there is a doubt in my mind one year on it’s this: that having broken out of a permanent role, returning to one would be a demanding prospect. That’s not to say impossible, of course. It might even be the case that what I’ve learned in a year of working for myself would make my participation in a group dynamic very different and more valuable in the future. Right now, it presents itself as the equivalent challenge to running a marathon.

Jon Jacob is an ICF accredited leadership coach, mentor and team facilitator. He also works as a freelance journalist, and digital producer in the performing arts sector. Find out more about his professional background on LinkedIn.

Email him at or call him on 07768 864655.

New Coaching vlog now available

I haven’t written about coaching for a long while. There are some very good reasons for that which I’m going to share in a post later this week. 

But in the meantime, I’ve started a new series of videos about coaching, my experience getting work as a coach, and specific my insights around getting stuff done as a freelancer.

The playlist of all the coaching videos is here. I’ll be adding to them every Monday (with any luck).  

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.

Develop the talent in your organisation

I’ve always held the view that the best thing an organisation can do for its staff is to develop them. It improves workflow, develops thinking, and enhances your end product. Doesn’t it?

Not every line manager I’ve had in my near twenty-five year career has shared that view. One challenged my desire to empower team members by pointing out that I was working for a business not a drop-in centre. For a long while I thought I was overly naive and needed to ‘shape-up’.

Andrew Mellor’s blog post on the Classical Music echoes the feelings I had when I left arts administration in 1997.

I regretted leaving arts administration

The picture at the top of this post is of me and my then newly recruited colleague Helen posing for the fundraising magazine, when I worked as an orchestra manager in Suffolk. I was twenty-three. I’d graduated from university with a music degree less than twelve months before. 

I loved my job as an orchestra manager. I loved the location too. It could have been ideal had the money been better (I ended up taking multiple bank loans in order to live), the conditions been a little less demanding, and the support been there to reassure me that yes I was doing a good job.

Arts administration had its perks: this is me at work talking to Dame Joan Sutherland in 1996.

I’ve written before about the more humorous recollections of being an orchestral manager, but the reality was that I felt hugely inexperienced, crippled by imposter syndrome, having to sell concert-playing opportunities to graduate musicians with a rehearsal schedule that didn’t have enough budget. That performances were a success was down to the talent on stage, but my feeling was – for the majority of the time – that I wasn’t the person they really wanted and wasn’t terribly good at the job.

I don’t think that now. The passing of the years has provided me with a far gentler, more forgiving stance. I think I gained far more experience doing the job than I realised, and probably did it to the best of my abilities. It was incredibly demanding for a 24 year old – still a recent graduate, having to take professional responsibility for people the same age as me, and judge them on the quality of their playing.

Is this all my music degree is good for?

The trigger to leave arts administration was down to one crucial event. The organisation I worked for was based in two locations that demanded a car journey between the two. I was based in one office for the day, and my new boss was in the other. “Would you come over to this building please? We need you to move the 150 chorus chairs from the top floor to the restaurant.” I saw red. I did what was asked conscious of the work I was having to leave behind in order to do a spot of stage management. Was this all my music degree was good for? Is this how they saw me? 

I handed in my notice the following day. I left to start working as an IT support engineer in a margarine factory in East London four weeks later. 

Me and arts administration now

It’s only been since I have started writing more and more about classical music on this blog that I notice the odd tang of regret about leaving arts administration back in ’97. Reconnecting with the performing arts because of the blog, but never really feeling as though I’m fully employed by the arts is a bittersweet thing.

A bit of me perhaps still hankers after a job in arts administration. And when I think of that, I start to wonder (and have said in a podcast with one chief exec) whether I was too quick to jack it all in and pursue the money.

There is an argument for saying that arts administration staff do need to accept that their roles will encompass all manner of ad-hoc tasks. Arts organisations have little or no money, so everybody needs to be prepared to ‘muck in’. Maybe I should have stuck at it. And maybe if I had I would have progressed further in arts administration. Maybe I only have myself to blame.

How I would have liked it to be

When I reflect on how I would like my time in arts administration to have been different, I end up thinking that I would have liked to have felt as though I was being invested in. I would have wanted to feel as though my contribution was, above the paltry salary, valued. I would have liked to know that there was a career path. I would have liked to have been able to say to somebody at the time, “I don’t think this is working,” or, “I need some help with this.”

Don’t get me wrong. I offloaded to colleagues a lot. Bored them to tears. But there wasn’t anything practical, useful or empowering to help me see my place in it all, and to halt my incessant ruminations that the difficulties of the job were all down to me.  There could have been so much more which could have helped me and in turn helped the organisation. 

Developing your staff isn’t as costly as you think

As part of my coaching business, I’m trying to offer the kind of skills I didn’t get when worked in the arts, back to the kinds of organisations I used to work for. Some I’ve spoken to have accepted that organisational dysfunction is hampering productivity and effectiveness. 

But, when it comes to tentatively discussing solutions, the message I get back is stark (and here I paraphrase, by the way): why would we invest in developing people when we accept that there will always be a high turnover of staff given the poor salaries there are? It seems as though retaining staff isn’t a priority, because its just not possible, so developing them isn’t either. But wouldn’t challenging that assumption, capitalising on expertise, and developing sector-wide talent be beneficial to the cultural scene as a whole in the long run?

The training and development that could have helped the organisation I worked for help me isn’t costly. That people think it is costly is down to their perception of what its worth and who they think ‘deserves’ to receive it. Helping organisations help their staff be the best they can so the sector can thrive through competition, aspiration, and emulation seems like a no-brainer to me.

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 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.