The move from the military to civvie street is one of the most significant career (and life) switches you can make. But for some, it doesn’t stop there.
We chatted with one of our own this week, Henry Dockerty (aka Doc), who landed a role post-REME that just wasn’t quite right for him. So he quit, went back to the drawing board, and found himself in a tech start-up. His story shows grit and determination. It’s a lesson to other service leavers that it’s okay to re-think your career. Nothing is final, and you should find the role that suits you.
Get unstuck! 👇
[Annabel] Hi, Doc. Thank you for talking to me today. Before we dive into your interesting journey, could you please just tell us a little bit about your military career?
[Doc] I don't tell many people this, but I actually joined the Royal Marines before I joined the army. I was 16 when I first applied, and only just 17 when I first joined the Marines and started training with them. That was a lot to take in when you're 17. I'd never been away from home before and all of a sudden I was away for 32 weeks on a pretty arduous training course. I was there for about 12 weeks before I decided that this just wasn’t the right time for me to be doing this. I was super homesick and struggling with being away from my family.So I made the decision to leave that for a bit and find another job. I always had the intention of going back and finishing after about a year.
When I went back to the careers office to rejoin the Marines, it just so happened the local careers office was a tri-service careers office, which means it’s RAF, Army and the Navy all in one. I was on my way through to the Navy area to speak to the Marine dude and I was caught by the army guy. He's like, “Where are you going? What are you doing?” And I explained. Then he said, “Just come and have a chat. Come and have a sit down with me.” And that was it. The next thing I was signed up to join the Army - which obviously wasn’t my intention.
After joining the military, you do a lot of tests, which help them channel you into different career paths. I got channelled towards aviation engineering, which did actually interest me. So after 12 weeks of basic training and almost two years of phase 2 training, I got into aviation. There’s quite a clear pathway within aviation when you're in the army, you tick certain boxes and you do certain courses and your progression is linear. I really enjoyed it.
[A] Incredible. So, fast forward then to when you're coming towards the end of your time serving. Can you tell us a little bit about that?
[D] So it's interesting because traditionally you sign up for 22 years. Which is an incredible milestone to hit. I left at the 16-year point, which was pretty rare at the time. A lot of people think that once you get to the 16-year point you might as well push on, do that last six and get to that 22-year point. But there had been some changes made to the pension structure which I took into account when I was making my decision.
But the biggest factor for me was family. When I speak to service leavers now, family has to be one of the top three reasons for leaving. The military is amazing but can be very tumultuous. You could pop into work on a Monday and be sent to Scotland for two weeks, so you miss important things, like kids’ sports days, parents’ evenings, birthdays, and all those important things. Eventually, it starts taking its toll. So, I decided to leave and started looking for something that would give me more stability. It wasn’t easy to leave. I never saw myself leaving early, and it was scary.
[A] I can imagine, especially if it's all you've really known in your career up to date. What role did you go into when you left?
[D] So I handed in my notice in 2019 - a weird time because COVID came along not long after, which changed a few things. But, with my experiences, I didn’t veer off the aviation path. I was an aircraft engineer in the military, and so I was going to be an aircraft engineer on Civvie Street. When I did the military career transition workshop, this idea of me staying as an aircraft engineer was reinforced. The really scary thing was just because of the timing of when I got out, aviation took a pretty big hit during COVID. So I went from about six months out with my feet up, looking at all these opportunities and just trying to decide which job I was going to take, to really starting to panic at about three months out when jobs were disappearing. I got to the stage where I started applying for anything with the word “engineering” in the title.
Eventually, through some networking, I got in touch with a hiring manager who was an ex-REME aircraft engineer. He happened to know of me, and I was invited to interview for an open role at the company where he worked.We did the interview in his driveway, on deck chairs over a brew. And I got the job!I worked there for just over two years.
[A] Hilarious, and so lucky. Okay, but then you had another career switch, right? How did you realise that that wasn't for you?
[D] I did a little bit of a pivot.
The one thing I really enjoyed about the military was that there's definitely a common purpose. You’re all a team, and you’re all working towards the same goal. And when you’re done with your task, you’ve got a tangible result, which is always amazing. My last role lacked some of that. It still had a cool purpose, but it just wasn’t the same. It was also quite repetitive, and that sense of teamwork and getting things done quickly just wasn’t there.
So I was at a point just before that two-year period where I started to look and to apply for some other opportunities that aligned more with what I wanted.During this time, I got to chat with Ben Read (Founder and CEO, Redeployable). We served together, were always close, and so of course we stayed in touch. He kept me up to date with his project and listened to my woes about my job, my experiences on civvie street since leaving the military, and what I was looking for in my next role. He propositioned me at that point and asked me to join him as the first hire of Redeployable. So I left my, stable, well-paid engineering job to join a brand new tech startup much to my wife's delight!
[A] Haha. I can only imagine what that conversation must have been like. What was it about the startup world in particular then that you liked the sound of?
[D] It stemmed back to having a purpose. I really liked the mission and the idea. And, because I’d fallen foul of not exploring opportunities as I left the military, the goal of exposing service leavers and veterans to all these other amazing careers, really resonated with me. And then the other thing that we mentioned earlier, was the idea of actually seeing the results of your work.
The military is big but it's not like you're in a massive company as you’re always operating in smaller units. The attraction of a start-up is that it’s small, and a lot is going on, but if you have a good week, the company feels it. There are tangible results.
[A] Definitely. But it is undeniably a huge career switch. Was that in itself challenging?
[D] Yes and no. When I think back to the military, your unit is like a start-up. Yes, it’s a big organisation, but it’s scrappy, you’re always getting things done, you often wear more than one hat, and you get chucked into the deep end of projects with minimal training, kit and time. And that’s what it’s like at a start-up. I didn't recognise that initially, but now having been in the start-up world for a couple of years, there's quite a lot of crossover from being in the military and working in this super fast-paced environment.
[A] You've gone through two career switches at this point, is there anything surprising that you've learned about yourself through this?
[D] I'd say I'm more comfortable with risk than I thought I was. I'd always considered myself a “safe” person. My friends always joked that I was 30 going on 60. So it really surprised me that I was willing to take this risk because you hear crazy stats like ‘80% of start-ups fail within the first few years’.
To be fair, though, working in a start-up does come with the flexibility I wanted. So I still tick that box now that I’m working for a start-up, despite the risk.
[A] Can you see any overlap between the skills that you were using when you were an aircraft engineer and the skills that you need now in your current role?
[D] Interestingly, there are a lot of skills that overlap. But the big one has to be adaptability. You’re often thrown into the deep end when working at a start-up, just like when you’re in the military.
Other skills are being meticulous and working under pressure. As an aircraft engineer, you have to be meticulous because you've got people’s lives in your hands. So there’s a lot of pressure to not slip up and make mistakes. When you’re in a start-up, while you might not have to worry about an aircraft crashing, there’s still a lot of pressure. And it’s all really fast-paced and results-driven. But, being able to work under pressure also means you can be thrown into any situation and still get the job done.
[A] I can see that. Ok, finally then can you think of any kind of actionable tips or takeaways for anyone really who's on the cusp of a career switch?
[D] The first thing would be to definitely consider other opportunities. Just because you’ve done a specific job for so many years, doesn’t mean to have to stay in the role. There are so many roles out there that you could be perfect for. Don’t be channelled into something because that’s what you’ve been told you need to do, or because you see other people doing it.
The second one is just network. It’s something I didn’t do well enough and only now am I seeing the value of having a strong network. It feels weird and unnatural to start with, reaching out to strangers on LinkedIn and pestering people to learn about their company or their role perhaps, but don't underestimate it. It's super valuable.
The third thing for me is to look into the hidden aspects of a job before you accept it. So on paper, my first role was amazing. It was good money. It had reasonable opportunities for progression. It was a good shift pattern. But you've got to dig into the sort of things that you don't necessarily see in the job description. Like what's the company culture like? How fulfilled are you going to be doing something like that? Is the progression as linear as it looks? And again, that's something you're going to achieve through networking.
[A] This has been great. Thank you so much. And to anyone who reading or watching this and would like to learn more about career switching, join the Redeployable Community.
[D] Yeah. We've got so many people in there now at various stages of this journey who are all willing to give others the value of their time and expertise, so get in amongst it.
[A] Yeah, absolutely. Thanks, Doc.
Key takeaways
Be open to different roles: Just because you’ve done a specific job in the military, doesn’t mean you have to stick to it on civvie street. You’d be surprised how transferrable your military skillset is.
Consider all aspects of a new job before accepting it: A role is more than just its job description. There are several things to think about when joining a new company, like culture, progression model, and whether you’ll be fulfilled or not.
Know your passions and what drives you: Finding purpose on civvie street can be challenging. But, if you focus on what you’re passionate about, you find the right role for you, even if it’s not necessarily in your wheelhouse.
Network, network, network: We go on about it. But having a solid network can help your transition, expose you to different opportunities, and even provide insights into a few “hidden aspects” of a potential new role.
Transitioning out of the military is a career switch all in itself. But sometimes you find yourself in a civvie role that just doesn’t serve you. There’s nothing wrong with changing it up again and trying something new. It might even lead to success - just ask Doc.
Head to the Redeployable community now if you want to connect with Doc, or veterans like him. Link here.
