My story

Ambitions vs. Obstacles: My Year in Review

Eating brekkie outside in the sun – a high point of self-employment during 2014.

Writing about a year is weird. A year isn’t a ‘thing’. It’s 12 months, in which a lot happens. How to sum it up? Why do we even feel the need to?

I don’t know, but for some reason it feels cathartic to do so. It allows us to move on from the themes of the last 12 months, and see the New Year as a fresh start. For that reason, it’s a positive exercise I think. And it gives me an excuse to finally write something here again after a long break.

I’ve loosely organised my 2014 annual review chronologically to make it easier to follow – although in some cases there is overlap between the sections.

An Ambitious Start

As discussed on the February episode of the Mountain Shores Podcast, I started the year with renewed ambition – to earn more money, and to finally be the consistent blogger I knew I was born to be, by publishing at least one post every week.

Neither happened quite as planned. In the end, I can confidently say I have earnt more money in 2014 than the previous year (although I haven’t totted up the totals yet) and I definitely earned it on a more consistent basis.

However as I explain below, my initial eagerness soon dissipated as I began to struggle with self-employment and my own self-imposed isolation.

January – March: Networking Works

Photo by Chris Scott

At the beginning of the year, I was networking happily and taking advantage of the great programme of events put on by Creative Edinburgh. I met a great new client at their excellent speed networking event in February. I was also invited to do a ‘lightning talk’ at the Talking Heads: Marketing & Design event in March front of 130 people at the Edinburgh College of Art as part of their ‘Creative, Cultural, Careers Festival’. I put a lot of preparation into this, and I think was one of the better public speaking appearances I’ve done (see slides below or on Slideshare).

Photo by Chris Scott.

I also signed up to be part of the Alive in Berlin team and was excited about attending the brand new event at the end of May. I interviewed several of the speakers, including Sarah Peck, Ben Austin and Dr. Carolyn Eddleston. I also completed a content strategy MOOC so I could expand my knowledge and help all of my clients on a more strategic level.

March/April: Parental Concerns 

My dad received two months of radiotherapy treatment for cancer during March and April after a long, uncertain wait, and is now thankfully recovering well. He dealt with it with such good humour and stoicism and I couldn’t respect him more. I was glad to have the freedom of movement that I was able to go over to Belfast and spend some time with him during April. My mum, who lives in Birmingham, also had a nasty fall around this time but is also thankfully much better now – again I was able to go and see her. This was a difficult time but I’m so, so grateful that they are both in relatively good health now.

May/June: Disillusionment and Daily Podcasts

2014-05-22_1400757181Throughout the year I bounced between short stints at local co-working spaces and coffee shops, but for the most part I only felt anchored and comfortable at home. That’s all very well in theory, but I’m also very aware it isn’t the best working environment for me due to the myriad of distractions (cat! Netflix! chocolate!)

My blogging efforts were (perhaps predictably if you’re a regular round these parts), far less consistent than my earnings. My initial burst of weekly articles whimpered to a halt after the first two months and a sudden and brief ‘attack of the daily podcasts’ throughout May and June ended the same way, after a misguided attempt at crowdfunding. Why? in both cases, I lost motivation, rather suddenly and completely. The worst part was, I couldn’t really understand why it had gone so wrong.

As much as I could be proud to have survived 2 years of self-employment, I wasn’t really enjoying the work mainly because I had no-one to bounce ideas off on a day-to-day basis. My blogging efforts felt in vain – I had barely made a penny from them and had no ‘passive income’ to supplement my work for clients, despite what I felt was a big investment of time and effort. I felt stuck, and trapped. Where to go from here?


I became very disillusioned with.. everything. I felt that I had made a lot of efforts at self-improvement over the past few years and yet still felt no happier about myself or any better able to cope with obstacles.

The idea behind this whole blog was largely based on the belief that we can all change ourselves for the better, so I felt like a complete fraud writing the usual positive posts here, or even publishing weekly extracts from my previous ebooks as planned. So I stopped.

Cold cruel envy, envy, envy, that most unattractive of traits, took hold of my heart with metal fists and squeezed, as I saw others achieve with seeming ease those things I wished I could but felt unable to. I knew they deserved their success because they were putting the work in and putting themselves out there, but I felt so stuck in my own inertia that I was no more able to make the necessary efforts to achieve what I wanted than to time travel or grow back a full head of hair. I lost hope, as my dreams and ambitions seemed unreachable, due to my own failings – which again, I could not fully understand.

The advice I had written sincerely and with the best of intentions at the time suddenly rang hollow to me as I couldn’t seem to follow it myself. I couldn’t face attending the ultra-positive ‘Alive in Berlin’ event whilst feeling that way, and with other work building up –  so I reluctantly cancelled my trip (thankfully I could tell from the feedback online that it was a great success anyway!).

Asking for Help

Having hit rock bottom in terms of motivation and hope, I realised I was in desperate need of help from someone qualified to look at the deeper issues causing my unhappiness and creative stagnation. I committed to weekly therapy sessions in April and have continued them since. That has been interesting, and life-changing, and tough. Sometimes things get worse before they get better.


I was still reasonably productive around this time however. I managed to attend the enjoyable and more local Small is Beautiful conference in Glasgow and write a guest post for them about superhero syndrome which touched on what I was struggling with, was honoured to be interviewed by my friend Gregory Berg for his Radio Enso podcast, to meet and interview author Farnoosh Brock and also chat to her hubbie when they visited Edinburgh, to be a literary guineapig for Canongate Books and to interview the Glaswegian author Anne Donovan for WOW247 who I also worked for throughout the Edinburgh Festival period in August.

July/August: Festival Fun


This was a pretty fun time as it has been the last couple of years as the festivals were in full flow and the weather was excellent. I enjoyed working half-day shifts making sure The Scotsman’s festival coverage was all online in good time, and catching up on other work in the afternoons. I went to a fair few festival shows with my wife and/or friends, including the cracking ‘Generation of Z’ where we got to experience the zombie apocalypse first-hand (sort of).

September: Divided Scotland


I couldn’t help get caught up in the debate around the Scottish Independence Referendum in September. The 45% of Scottish residents who voted yes, of whom I was one, had many different reasons for voting for Scotland to become independent. For me, the possibility of establishing a fairer society was foremost, rather than any strong desire to be separate from English, Welsh and Northern Irish people (after all, I was born in England and have friends and family throughout the UK).

One poll suggested we might have a chance of winning it, but in the end it wasn’t to be as the majority decided to remain within the UK and under the rule of what I consider to be the corrupt Westminster Government. The result felt pretty devastating for those of us who voted Yes, as we had allowed ourselves to hope for a chance at building a ‘better nation’.

Having said that, the positive efforts by Yes campaigners including the National Collective proved that art and activism go hand in hand, and a renewed belief in the power of grassroots campaigning has given many people in Scotland a strengthened commitment to fighting for social justice in whatever way we can, so I believe positive things have come from it.

October – A Chap, on a Mac

2014-10-28_1414487272I solved my persistent IT problems by splashing out on a new MacBook Pro, however the effect on my finances was not good and I had to abandon my cushy new co-working desk at CodeBase Edinburgh that I had only just secured. But I did discover that an ironing board makes a great standing desk.

After a year of moderate boozing (following my year of no alcohol) I decided to take a break from it again at the end of October after a particularly unpleasant hangover, and have managed over two months of sobriety so far.

November/December: Good things do happen to good people

I was delighted when my good friend Sean Michaels won the Giller prize (and an amazing 100,000 Canadian dollars) for his book Us Conductors. His acceptance speech and subsequent interviews clearly demonstrate his remarkable way with words and good nature. The book reads like a true literary classic – it’s a fictional account of the ridiculously unlikely but completely true story of the inventor of the theremin.

[tentblogger-youtube hI0iAP1PVWA]

My friend and sometime client Johnny Lynch aka The Pictish Trail also celebrated the successful one year anniversary of his label Lost Map as well as being signed to ‘hip’ London label Moshi Moshi earlier in the year.

In November I was also lucky enough to chat to Robert Wringham, publisher of New Escapologist magazine, along with my usual Mountain Shores co-hosts, Fabian and Michael. Robert’s book ‘Escape Everything’ has almost reached its crowdfunding target so there’s still time to help fund what sounds like it will be a brilliant book.

A few other of my good pals and friends of this blog also put out their own books during 2014 – Michael Nobbs published full colour versions of the first 3 issues of his journal The Beany, Dave Ursillo penned Big Apple, Black Sand and the Midnight Sun, a thought-provoking and inspiring travelogue (as well as completing his yoga teacher training), ‘Writing Man’ Paul Forrester published ‘A Tour of the Indies: A Creative Quest For The UK’s Best Cinemas … And Cake’, Emily Dodd published the children’s book ‘Can’t Dance Cameron’ (amongst her many other achievements) and Margaret Pinard has published her second novel. I also helped my pal Dougie publish his short Kindle book ‘Things to Talk About When There’s Nothing to Talk About’ with another full-length book we’ve been working on coming out sometime in the New Year. (Apologies if I’ve left you out of this section due to absent-mindedness – please do tell me about your achievements in the comments!)

Meanwhile Lis and Nine both had a very difficult 2014 but wrote beautifully about it and inspired me to break my silence and write something too (however flawed it might be).

And me? I haven’t solved all my problems around my work, but I know I am very lucky to have employment. I’m grateful that my wife and cat continue to patiently put up with me – and I have a wider and better support network in place now than I did before.

That includes my continued weekly therapy sessions. I’ve learnt a lot about myself that I didn’t know before. I’ve begun to face up to some deep-rooted and unconstructive patterns of behaviour and thought. It’s going to take a while to deal with those (like, the rest of my life). But I feel hope again. I have identified a pattern of isolating myself and trying to do everything on my own for reasons of pride and fear.. but I’m slowly learning how to reach out for help and how to make more positive choices.

In 2015, I will make a sincere effort to be grateful, joyful, useful and perhaps a little bit playful on a daily basis.

See you then.


p.s. I’d love to hear from you in the comment section about how 2014 went for you and your intentions and hopes for 2015.

34 replies on “Ambitions vs. Obstacles: My Year in Review”

Hi Milo

Have read this on my commute on the way to my first day back at work in a week. I must say it’s an inspiring and remarkably honest read.

It sounds like you’ve had a tough year, but come through it with an air of positivity and a lot more self-understanding. Hopefully it bodes well for you in 2015.

Keep up the great work mate. Good things will come.



This was great to read, and enhanced by your frankness in talking about the obstacles you’ve encountered this year, as well as about asking for help. I’m glad you included those parts, and I hope you feel okay about having included them too. I also started therapy this year, actually, although it didn’t last (money! But thankfully I’m doing better anyway, and it was good to have it while I did). Hopefully 2015 will bring better things – especially now that we’ve spent some time working out what’s wrong and how to fix it.


Hi Milo,
Thanks for your 2014 summary.
I found building/being part of a team and making it work was my biggest challenge this year.
Great tip for the ironing board!
All the best for 2015 from Buenos Aires, Argentina.


Sounds like a big challenge Vincent, glad you’ve been able to make it work. I would love it if ironing board standing desks became all the rage in Buenos Aires! 🙂


Hi Milo, I always admire your honesty. I know from experience that it’s not easy to make life style choices that mean financially you are insecure but be proud that you are brave enough to do it. Hope 2015 will bring more positive experiences your way.


Thanks very much Helen, appreciate you taking the time to read and leave a comment. Self-employment certainly been a learning experience! Hope your 2015 is positive too.


Well done, Milo! I found your amazing recap through Michael Nobbs’ Facebook mention. My only comment is that I prefer my cat as a freelance cohort to some of the human speed-bump co-workers I’ve endured.


Interesting post, Milo. When I was doing my freelance training I used to try at least once a week to meet up with at least one work-related friend (kind of introvert networking). Good for motivation, fun, ideas, and contacts.

Glad the therapy is helping. I’ve been through 3 lots now, last years’s being the most intense. I finally got to a place in the last lot where I could accept myself and stop using ‘self development’ as a way of trying to be perfect. It has been a very painful process and at the same time the best thing I could do for myself.

Hope 2015 feels lighter.


Hey Alison, thanks for commenting! That’s a good idea. I often feel like hiding away but it would be good to be a bit more consistent about meeting up with people.

Love what you say about stopping “using ‘self development’ as a way of trying to be perfect”. Amazing how much pain we can cause ourselves because of lack of acceptance. I love the phrase ‘progress not perfection’.

Hope you have a great 2015 too 🙂


Milo, this is great! If anything, a look back at your year shows how much you HAVE accomplished, things that range far and wide and show the diversity of your interest AND abilities. Do you have Mastermind groups in Edinburgh? I know you’ve got the Mountain Shores lads, but perhaps something in person would give you the structure and social support you’d like. I’ve been with a great group (only 3 of us, looking for a 4th) since July, and it’s really helped me to be more rational and measured about my own efforts. Just a thought for a tool you might like. 🙂 Here’s to a great 2015!


Thank you Margaret! I appreciate all your support 🙂 Great tip – I don’t know how many formal mastermind groups there are locally, but I’m sure I could find some others who are willing to start one up. Indeed, here’s to a great year!


It’s good to hear from you again, Milo. This post reminds me of one of the first (if not the first) of the micro-podcasts. The tone there and in this post seems more personal, perhaps more “honest” and therefor it comes across so much stronger. Maybe trying to adhere to a fixed blogging-schedule is not necessarily the thing to strive for.

As you know, I struggle with similar difficulties as you do in making work and making it work. I hope we can both make some progress at this the following year.

I managed to – finally – get my new blog started earlier this month. I stripped all the ideas I had for this new site to the bare minimum: a simple blog (I plan to add other features later as I go.)

All the best for the new year, Milo. Write hard.


Hi Gilliom! Yes, maybe once or twice a year is enough? That would certainly take the pressure off 🙂

Excellent news about your new blog, it’s good to see your daily doodle there. You could also try instagram, seems an ideal outlet for those.


A great post and all the better for being honest. I think most people who are self employed or run their own small business selling services have these doubts. I try not to listen to positivity porn where people pretend that everything is wonderful. It’s just a standard that none can live up to. Look forward to seeing what you do next year.


Thanks Pete. Yes, I find it hard to identify with ultra-confident aggressive business types, maybe that’s my problem? Thanks for commenting and hope you have a great 2015.


Wishing you a very, very happy new year, Milo. Thank you for sharing your downs and ups – for the generosity and bravery of it. As you know, we all have secret struggles (even in the best seasons), and it is a huge reassurance and gift to hear a little about others’. Please know that I’m here and would love to talk if you ever need someone far away to talk to, and even though I’m pretty shit on skype. You are extraordinary and I am so excited for (y)our coming year.


I’ve spent much of this year avoiding going back into psychotherapy: I don’t think I have anything more to talk about, honestly! I know what I need to do. And so many of the reasons I had to take time off work and increase my medication were things out of my control, anyway.

But I’d recommend the process, and it sounds as if it’s providing you with the independent sounding board I think it’s necessary when you spent so much of your working day alone with your thoughts, letting the brain-weasels tell you that what you’re doing isn’t good enough. The fact that you’re able to make a living at all from freelance work is marvellous. I couldn’t do it.

I’ve made one “resolution”, going into 2015… I’m going to make a list of the tangible things that I achieve at the back of my journal as I go through the year. It’ll make it as easy to reflect on self-development this time next year as I find listing my favourite albums. I got so lost, particularly in the second half of the year, that I forgot so much of what I did (getting oan the telly, earning enough freelance to have to actually pay tax on it, volunteering at the Commonwealth Games, fighting for a pay rise…)

Let’s hang out more next year, ok?



Yes it is helping Lis. Glad you found it helpful too. I thought I would commit to a year and see how I feel about it then.

And thanks- I’m SURE you could be a successful full-time freelancer given that you do so well at it alongside your full-time job – but at the same time I can’t say I would recommend it (the brain-weasels have proven to be a problem!)

I really like the ‘back of the journal’ idea. You achieved loads this year! I set up a ‘Feelgood file’ in Mailbox for nice emails but forget to look back at it.. I do think paper and pen tend to win out with this sort of thing.

Anyway, it would be great to hang out more 🙂


Hi Milo, I must say this is such a refreshing look back. It demonstrates the ups and downs in a year that we all face and how we just have to keep plugging away. I’m so glad we connected several years ago through Melissa Dinwiddie’s site. I hope 2015 is a beautiful year for you.


Thanks very much Kim! I’m very glad we connected too – love seeing your pics on instagram and am impressed by what you’ve achieved on your blog. A very happy new year to you (when it arrives!) 🙂



Thanks for sharing.

I very much enjoyed our chat earlier in the year, and I hope that we can stay in contact in 2015. As someone who has had to come to terms with the life of a freelancer — very different to being a lawyer! — I completely understand where you’re coming from. In my case, as trite as it sounds, I take one day at a time, and do my best to improve those areas of my life that I think will bring me lasting happiness and those that I love.



Thanks very much Julian, yes it would be great to reconnect soon! The ‘one day at a time’ concept is very useful, well done for all of your output this year and all the best for 2015 🙂


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