Ben Howdle

Ben talks about launching his latest product, freelancing with a family and what freedom has meant for him.

Tell me a little bit about yourself and what you’re working on right now.

I’m a 27 year old married man with two kids, living in Worcestershire, UK. I’m self-employed and I’m currently splitting my week in two; one half as a contractor for Plasso, as a full-stack developer, and the other half maintaining my new product Ekko which lets you create a website from your Facebook page.

What was the defining moment that you decided to go freelance?

Seeing as I originally started freelancing back in 2009, it’s a bit of a tricky question. If anything, I actually see that time of freelancing more as “moonlighting” because they were always projects which I worked on in the evenings and weekends around a full-time job. However, when I decided to jump across to full-time freelance and leave my then full-time job at KashFlow, it was near the end of 2013. KashFlow had been acquired by a much larger company and there were big changes going on, in terms of the product and the team, ie. new location, integrating with the new company’s employees, etc…around the same time, my “moonlighting” freelance has been on the upturn and I had just been offered (verbally) multiple projects with a large digital agency, and they needed a quick turnaround. Once I had the “promise” of that income, I decided now was my chance to make the leap…

You can never count on income until it’s in your bank account

Turns out, you can never count on income until it’s being transferred into your bank account. Those multiple jobs never came in, but luckily, because I’d decided to go freelance, I quietly spread the word amongst a few people I know and they were kind enough to pass my name on for potential work. So by the time my notice was served with KashFlow, I had my first contract lined up and my first day-rate established (I’d previously been giving people fixed costs for projects, which inevitably led to scope changes and me being too inexperienced to account for this).

Did you transition to freelance or jump right in?

Unfortunately I think I answered a large part of this question in the above question, however it’s worth mentioning that I’d been “moonlight” freelancing for 4 years before I properly jumped across to full-time freelance. I’d love to say that 4 years of freelancing prepared me for full-time freelance, but, I don’t think it really did.

I’d love to say that 4 years of freelancing prepared me for full-time freelance, but, I don’t think it really did.

The moonlighting freelancing was always a bonus, or a top-up for an existing salary. It was never 100% necessary that I did it, I just enjoyed learning stuff outside of my normal 9-5 and luckily people were happy to pay for this work. I saw doing the moonlighting freelance as jogging on a treadmill one moment and then attempting to jump across to a treadmill going full-pelt. You’ve just gotta adapt to a new pace, different challenges….very quickly.

Being remote gives you a lot of freedom, especially in regards to routine. What’s your typical routine?

Having kids is a blessing in disguise for freelancers I believe (most of the time), I feel like they provide anchor points in the day which otherwise, I think I’d struggle to maintain any sort of structure to my day. I get up around 7am, make breakfast, have a bunch of coffee, get ready and aim to be at my office for around 9am. If I’m not going to the gym that day, I’ll likely work until midday then head home to have lunch with my wife and our 18 month old son. I’ll head back to my office and work until 6pm-ish, occasionally it’ll be later, but not too often at all. If I am going to the gym that day, I’ll come into my office for 9am, work for an hour, then drive 25 minutes to the gym, workout until 11.30, head into Cheltenham town centre, grab some lunch and work from various coffee shops until either a) I don’t want to be out any more or b) the internet will be unreliable and I’ll leave Cheltenham sad. I’ll usually head back to my office and work till a similar time, 6-6.30. At the moment, I’m right at the precipice of putting my own app into beta, so I’m usually working in the evening on that. 

Working remote can be lonely. Do you make any efforts to be around other people?

I’m one of those annoying introvert people, so I tend to get lonely fairly quickly, but then also crave solitude after being around people for too long ¯\_(ツ)_/¯ 

I’m one of those annoying introvert people, so I tend to get lonely fairly quickly

Working in my own office is great for focus and privacy, etc…but terrible for having normal interactions with people. This is why I go and work in coffee shops a few times a week, just to be around normal conversations…I rarely wear headphones unless there’s something I really need to concentrate on, I enjoy working with the background hum of chatter.

In 2014, we moved from Kent back to where me and my wife grew up (well, 1/2 hour drive away). This meant we were back near people and family we knew, so it’s been great for personal relationships. However, the town we live in is a bit scarce for things like co-working spaces, and working coffee shops. Hence me driving 25 mins to Cheltenham for the gym/better coffee shops. Ideally, I think I’d like to work in an open plan co-working space, but with the option to use private rooms for Google Hangouts/the odd bit of peace.

Is there any one thing that’s transformed the way you work freelance or remote? Whether it be a software, a tool or a routine. 

I’d have to say, having our son. Before he came along, our daughter was at nursery most days and my wife was keeping herself busy, so I had my office at home on the top floor. This was great, apart from the fact that home/work were very much intertwined, and I’d have a horrible habit of not getting dressed properly after breakfast and just dragging myself upstairs to my desk, and then at the end of the day, coming downstairs and struggling to disconnect from the work I’d been doing 14 seconds earlier.

However, when our son was born, I almost immediately got a contract with Cisco, which meant daily calls at 5.30pm. And I don’t whether you’ve tried to have a Skype call at 5.30pm when your wife is trying to feed/bathe two kids under 4, but…it’s noisy. I felt awful, because this was their home as well and I felt like my work was interfering with trying to keep a chill home life. So, I looked around and found an office I could lease. Perfect. This got me out the house, dressed, and I could do my 5.30 calls without bothering anyone. Right around this time, a friend recommended I came along to CrossFit with him, which meant I’d be out the house by 6.30am three times a week, getting physical exercise, coming back to have breakfast with my family, and being at my office by 9am. Lovely stuff.

As you have a family, how does working remotely affect that? 

They see me more. When I was working in London, I used to leave the house at 7.20am, get a train into London for an hour or so, work until 5.30, get another train back, and arrive home at 7.30pm, *just* in time to see my daughter before she went to bed. On the other hand, I think being remote can almost give you too much freedom, and I think you can all start to get on each other’s toes somewhat.

My family see me more

I’d be seeing my wife for a large portion of the day, so by the evening we’d have nothing really to tell each other about our day, because we’d been together for most of it. I think the best thing about working remote is that you can manufacture a scenario that works for you. No, I don’t need to commute into London for 3 hours a day, but occasionally I’ll jump on a train to Bristol for a change of scenery, or have a coffee with someone. 2013 was me working in London, barely seeing my kid (only one at that time), 2014 swung the pendulum completely in the opposite direction and I rarely had a reason to leave the house. Too much of a good thing maybe?

Sometimes work doesn’t come easily! When it comes to getting work, how do you generate leads? 

I’m terrible at this. When I need work, I send out a couple of tweets, and I wait….

And wait…


And then I panic.

And then, a couple of weeks later, I’ll get something come in. This happened just after our son was born in March 2015. I didn’t have any work on, and decided I should really get some. So I announced my availability on Twitter, and nothing came in, for 5 or so weeks. And then, someone recommended me to a London startup, and then the following week, someone recommended me for the Cisco contract. Now, there could well be some correlation between that initial availability announcement, and those two contracts coming, but it didn’t feel like it! 

However, when I finished Cisco in July 2016, I had intended to take August off and spend time with my family (with my daughter being off school for the summer holidays), with the plan that I’d starting looking around for work in September. Near the end of August (maybe the last few days), I put out a couple of tweets, and nothing really came in. However, because this had happened last time, I was a lot more chill with the fact that it could be a little while before anything surfaced. Luckily for me, Drew Wilson at Plasso was looking for a developer and again, someone mentioned my name to him and a few DMs later, I was digitally signing a contract with Plasso.

What’s one piece of advice you would give to someone wanting to go freelance?

You will panic, this is fine. You will want to say YES to every request that comes in…I believe this is also fine. There’s lots of blog posts out there about avoiding burn out, and looking after yourself, and I definitely am not advocating the opposite of that, but I do think there’s a silver lining to working yourself into the ground – you fully appreciate that that isn’t the way you want to work and live. I feel like it could be an unfortunate rite of passage that freelancers go through. I did it once, for a few weeks at the start of 2014, where I was working on one project from 9-5, then I’d accepted some emergency work from a London digital agency who were desperate for some work to be completed so they could deliver it to their client, so I charged a higher rate and agreed to work evenings and weekends around my other contract. My hours were roughly 7am-1am (obviously breaks for meals, washing, toilet breaks etc…I’m not a savage) for roughly 2-3 weeks. I was a zombie. Completely on auto-pilot. However, now that I’ve experienced that way of working, I know how to plan my finances better, manage my time better and handle enquiries better. 

Nothing makes you find work like the pressure of paying rent

Lots of people say, “save up 6 months salary before going freelance”. I can’t really argue against that, because it’s very sensible. However, I went freelance on the verbal promise of £12,000 for 40 days work, which never came in. At the same time, we were moving house and I’d just quit my London full-time job. Nothing makes you go out and find work like the pressure of paying rent or feeding a small child, even if I didn’t unclench my arse for a few weeks.

People can work remote even in a job, what advice would you give to someone wanting to go remote?

Usual advice I guess – physical exercise is a great excuse for leaving the house. Depends on where you’re living (ie. what sort of town/city) but maybe trying to find places (ie. coffee shops, coworking) that you can occasionally work from, even finding someone else close by who’s also remote, and working with them.

Having a base is very important

I think having a base is very important, whether that be at home, or going and getting your own office, you’re going to want to find somewhere you know you can have reliable internet and a quiet place to make a call. Working from coffee shops is nice and tasty, but the internet/volume is a pure lottery.

What’s been your biggest challenge freelancing or working remotely?

For me personally, it’s been finding a balance between the structure that comes with a 9-5, and the freedom that comes with remote freelancing. I honestly want my cake and to eat it. I’m still trying to find that holy grail of being around people, having the odd chat, or bouncing ideas off someone, but then also having the freedom to go to my daughter’s assembly at her school on a Friday morning to watch her receive a certificate. Find a structure that works for you. I know a lot of people would want to work from 7am-3pm and then be done for the day, however, if you’ve got American clients, this probably isn’t very feasible, so find hobbies, or exercise that you can dot throughout your day, so you’re not stuck at home, talking to your cat all day.

You can follow Ben on Twitter @benhowdle

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