Working for yourself, or even just by yourself, is a tempting idea for many people but not always an option. I thought it would be interesting to hear from some others in Ireland who have decided to take control of their own time and work remotely.

Introducing Jamie Lawrence. Jamie is a web developer living in Cork. With a skill set that covers not only the full technology stack but also how to apply it to real business situations, he’s well qualified to be considered “your interim CTO”. He was kind enough to answer some questions I had about what it means to work remotely, set your own terms, and fear less.

What sort of work do you do?

I’m currently a Rails and Javascript developer but I market myself in the wider context of an “interim CTO” because I’m more interested in business / startups / copywriting / marketing / sales etc than just coding.

For how long have you been working remotely?

I worked in IBM for 5 years, 3 of which were spent working remotely for projects in the US. For over 18 months prior to March I worked for myself, mostly from home. Since March, I joined my client’s company as CTO working onsite in the office in Cork.

Were you working full-time in an office before? If so, what prompted the change?

So, I’ve had a checkered history. I’ve worked in offices 9 - 5:30 wearing a suit and tie and I’ve worked in relaxed open spaces with no fixed hours. In IBM, I was working in the Cork office, which was originally quite “small company” but quickly became very “big company”. As it grew, the work became more diversified and most of us ended up working on projects that were run entirely from the US offices. For about 18mths I was the only non-US employee working this project with 10-15 other developers and testers. Some of the US employees worked remotely from home but I was still based in the Cork office even though all my colleagues and management structures were based in the US.

It was an odd time. More Irish employees joined the project but we were still remote despite sitting in the same building. We’d have daily “stand ups” over the phone and that was how I knew what the testers a few desks over or the doc writer upstairs was working on. Occasionally, I’d go over to their desk to walk them through an issue but maybe only once or twice a week. We mostly communicated with email, issue tracker and Sametime (IM)

Ultimately, I left because I was really depressed and fucking hated the work and company. I wanted more control, more influence over the work I did, more choice in the technologies that I used, etc.

Where did you work from? (Converted attic, shared working space?)

I worked from a spare room upstairs at home. It was always set up as an “office” for the iMac, photo processing etc. but this was the first time I’d used it for a job. Later, I took a part-time desk in a shared space for 1 day a week to give myself a solid interruption-free day of work. For the last six months, I took that desk full-time and used it 3 or 4 days a week.

Do you work remotely all the time, or part time?

All the time when I was working for myself. Even though my client was also in Cork and wanted me specifically because I was local, we only met in-person once every 3-4 months.

Did you have multiple clients / projects?

No. I always felt like I was a failure as a freelancer for only having one client… but then I realised that the projects I wanted were not of the 6-8wk variety. I wanted long-term engagements where I could work closely with and influence the client’s business over an extended period of time. Also, he was happy to keep giving me as much work as I wanted (I aimed for 20-25 billable hours a week) so there really wasn’t room for taking on another client. In the future, I’d like to have a one or two 2-5hr/wk retainers plus one bigger client, but I think it takes time to build up to retainer work.

What would you say are the best and worst things about working remotely?

This is a loaded question and probably a good time to unpack the 3 issues at stake: working remotely, working at home, and working for yourself. Each have their own distinct advantages/disadvantages although they overlap.

Working remotely:

The good:

• I enjoy the location freedom and being able to choose my best work environment.
• I can limit the distractions (e.g. setting a DND status is easier than physically blocking someone from talking to you)
• I can listen to music, etc

Not so good:

• Some problems are best resolved face-to-face and it probably helps if you’ve met the people you’re working with at least a few times in real life

Working from home:

The good:

• No commute (though mine was only a 20mins commute any way)
• More flexibility to see the kids (I could take them to school, or pick them up, or time my lunch break to coincide with when they came home)
• I kept up with small jobs around the house like tidying the office, or putting on the dishwasher, or fixing a toy. I’m not sure if that’s a good thing but, if I needed a break, at least there was something productive to do whilst I mulled over a problem.

Not so good:

• I got distracted easily (e.g. if my mum came over in the afternoon or if it was a beautiful day)
• I could hear the kids if they were screaming (happily or not). It’s hard to get dragged into little family dramas (someone falls over, the meat for dinner had gone off, etc, etc). It took a few months to educate the kids that I was working upstairs but then they mostly got it. I might get some noise-cancelling headphones soon though.
• Less reason to get out of the house, leading to manic episodes at the weekend where I’d need to escape.

Working for yourself:

The good:

• Set my own hours. I looked back and realised that my brain doesn’t slip into “coding mode” until at least 11am, but more often 2-3pm. Why the hell had I been wasting 3 or 4 hours each day of my time, sitting at a desk being unproductive, for the past 10 years? That’s like 7500 hours of my life being wasted. I felt that I certainly couldn’t charge for this unproductive time so I’d use it for something else that would make me happier and more productive for the hours I charged for.
• So I can swim in the mornings. Or maybe take a walk. And sometimes grab brunch in Kinsale. This had the single biggest positive effect on my life and I’ll defend it at all costs.

Not so good:

• Worrying about where to get more clients (employees suffer from depression because of the lack of control over their destiny; freelancers suffer from anxiety worrying about the next client etc — I couldn’t have it both ways!)
• Accounts, bookkeeping, taxes, VAT returns, etc. even though I have a great accountant

Socially, do you attend meet ups or conferences to network?

I used to run the Ruby user group in Cork just so I could meet some like-minded people although it was really small. I stopped running it earlier this year when I stopped freelancing but I make sure to attend some of the local events (CorkDev, BuiltInCork). I wish Cork had a more vibrant tech scene like Dublin though, and having a wider group of people to mingle with. I do 1 or 2 conferences a year in Ireland / UK / Europe but I’d like to be able to justify 3 or 4 in the future

What would you recommend people do if they are thinking of moving from full-time employment to contracting or remote working?

Try to do a little moonlighting in your spare time, particularly if the work will be different to your current employment.

Decide who your perfect client would be and what makes you different (unlike full-time employers, clients don’t care about your CV. They just care about what you can do for them so you need to be able to sell yourself).

Try to book your first client before your leave your job (they might say they need you now, but tell them you’re busy and have a slot opening up in a month — then resign).

Have a little financial cushion to cover initial costs, payment delays etc. but…

Fear less. How long did it take you to get your last job? How in-demand are your skills? As a developer, I’m pretty sure I could get a full-time job in a month if I needed to.

Lastly, read everything that Brennan Dunn has produced. The Freelancer Show is also an incredible resource (go back to the start) and they’ve recently run a “preparing for freelancing” series of episodes.

How do you tend to find clients?

Mostly they find me though my website, word-of-mouth and by Googling “ruby cork” and finding my meetup page. I’ll have to make a more concerted marketing push in the future though.

When approaching clients, do you find selling an hourly service preferable to value-based pricing?

I charged hourly but I’d like to change to a day/weekly rate and some more productised consulting approaches. I’m specifically thinking of augmenting my developer/interim CTO roles with a product for analysing, predicting and mitigating churn in SaaS apps. Initially this would be “flintstoned” (part software, largely my effort) before moving to a fully-automated approach.

Is late paying / non-paying ever an issue? How might you handle it?

Rarely an issue for me but, in general, yes. I worked in two-week sprints, billed at the end of every sprint and had non-negotiable 15-day terms. That meant that product development was always in-step with the income. My contract also states that I cease work (and retain the intellectual property) if an invoice remains unpaid… so, at most, they’d get 1 month (i.e., 1 sprint + 15 days) of work out of me for free. If possible, I’d also take an initial deposit of 2 to 4 weeks to cover this.

Ever had to fire a client?

No. Though I probably should have transitioned my last client on to a full-time team sooner.

Overall, would you recommend remote working?

Dear Recruiters, if you want me to move to Dublin you should know that you're competing with this pic.twitter.com/oibCZveguu

— Jamie Lawrence (@ideasasylum) July 13, 2014

Hell, yes!

Location freedom is important, but it’s more important to me to have time-freedom. All those wasted hours at my previous jobs still haunt me. Why should 40 hours each week be the standard?

Thanks, Jamie!

If you enjoyed this interview (or if you didn’t), please let me know on Mastodon or email. If you have experience working for yourself and want to add something, do get in touch.