Making the move with Direction, not just a Departure Date

Leaving the Armed Forces isn’t just about finding your next job. Career Strategy coach Jenny Roberts explains why the real question is – where do you want your experience to take you next?

For many experienced Service leavers, resettlement isn’t really about proving you’re employable. You already know your CV stacks up, years of leadership, operational delivery and decision-making under pressure don’t need a sales pitch. The harder question is this: where should all of that go next?

That’s a very different problem to solve, and it’s one Jenny Roberts, founder of Jenny Roberts Coaching, and creator the Military to Market programme, spends every working day helping people answer.

Jenny brings a perspective few career coaches can match: she left the RAF and went on to spend more than 13 years in civilian recruitment and hiring, working on roles for major employers including Rolls-Royce and BAE Systems. She’s sat on both sides of the table – as a Service leaver herself, and as the person making the hiring decisions afterwards. 

“My clients are often highly experienced people with plenty to offer,” says Jenny. “What they need isn’t someone to tell them they’re capable, they already know that. They need a clear view of where their experience fits, what level they should be operating at, how the market will perceive them, and which opportunities are genuinely worth pursuing. That’s where the transition actually starts.”

It’s a subtle but important shift in thinking. Most resettlement support is built to answer “can I get a job?” Jenny’s work starts from a more ambitious question: “what’s the right job, at the right level, for the career and life I actually want to build?”

BREADTH IS AN ASSET – BUT IT NEEDS DIRECTION
A military career builds a breadth of experience most civilians never get near: leadership, operations, training, projects, technical delivery and strategic planning, often inside the same decade.

That breadth is a genuine advantage. It’s also, Jenny points out, exactly what makes the transition harder.

“Project management may fit. So might operations, consulting, logistics, engineering management, learning and development, security, defence or the wider public sector,” she says. “The important question isn’t what could I do? It’s where do I want my experience to have the greatest value next? That’s a more ambitious question, because it asks you to think beyond employability and towards fit, level and long-term direction.”

For someone who’s spent years building a serious career, Jenny argues, that deserves serious thought – not a rushed decision made in the final months before discharge. She encourages clients to sit with questions most resettlement briefings never ask:
•Do you want to keep leading teams, or move into something more specialist or advisory?
•Do you want pace and complexity, or more stability?
•Do you want to stay close to defence, or step deliberately into a new market?
•How much do salary, geography, flexibility, travel and family life weigh in the decision?
•What do you actually want to be known for in your next career?

CVS AND COURSES SERVE THE DIRECTION – NOT THE OTHER WAY AROUND
Resettlement offers plenty to keep you busy: courses, qualifications, CV workshops, LinkedIn profile-building, networking events, job boards. All of it can be valuable, but only once it’s serving a clear direction.

“A strong CV doesn’t create a career strategy,” Jenny says. “A qualification doesn’t decide where your experience fits. A recruiter can introduce opportunities, but they can’t decide which ones are right for you.”

Get the direction clear first, she argues, and everything else in the resettlement process becomes sharper and more efficient. You can judge whether a qualification is genuinely relevant rather than just available. You can network with a purpose instead of collecting business cards. You can position your experience for a specific market rather than trying to look broadly appealing to everyone. And you can assess opportunities against the career you’re trying to build, rather than simply asking whether you could technically do the job.

“For experienced Service leavers, the goal shouldn’t be to become more employable in the abstract,” Jenny says. “It should be to become more precisely positioned.”

TRANSLATE THE LEVEL, NOT JUST THE LANGUAGE
Most resettlement advice focuses on stripping out acronyms and rewriting job titles into something a civilian recruiter recognises. Jenny says that’s only half the job – and often the less important half.

“The more important task is helping the market understand the level at which you’ve operated,” she explains. “What were you responsible for? What was the scale? How complex was the environment? What decisions did you own? Who did you influence? What changed because of your leadership or judgement? Those are the questions that actually reveal value.”

This matters most for senior and experienced Service leavers, Jenny says, because being new to a civilian sector doesn’t automatically make you junior. You may need to learn new systems, terminology or commercial expectations – that’s part of any transition – but it doesn’t erase the leadership, operational judgement and accountability you already bring.

At the same time, military seniority doesn’t simply transfer across unchanged. The real work, she says, is calibration: working out where your experience genuinely places you in a given market, where you’re already credible, and where you’ll need to build evidence before employers take a level of seniority at face value.

“That kind of thinking prevents two common mistakes,” Jenny says. “Underselling years of experience, or assuming that military seniority alone guarantees a direct equivalent outside. The right answer is usually more nuanced, and far more useful.”

LET THE MARKET SHARPEN YOUR JUDGEMENT
Jenny is clear that transition planning shouldn’t happen entirely from behind a laptop. Job descriptions and course brochures can only tell you so much, the market itself will often answer questions they can’t.

“Good networking isn’t about collecting contacts – it’s about intelligence,” she says. “What does this role actually involve? What makes someone successful at this level? What would an employer value most in my background? Where would they have concerns? How does someone with my experience typically enter this sector? What does progression look like?”

The more of those conversations you have, Jenny says, the more accurately you can judge your options. Sometimes they validate a direction you’d already picked. Sometimes they reveal that a role is smaller than it looked on paper. Sometimes they show you’re aiming too low, and sometimes they make it clear that the obvious path isn’t actually the most interesting one.

“The aim of exploration isn’t to keep every option open,” she says. “It’s to collect data and to become increasingly deliberate about which options deserve your attention.”

YOUR FIRST MOVE DOESN’T HAVE TO CARRY YOUR WHOLE FUTURE
With fixed leaving dates, salaries to think about and families to consider, there’s real pressure around the first civilian role. Having an offer on the table can bring enormous relief, Jenny understands that pull completely.

But she pushes back on the idea that the first role has to be right forever. “Your first civilian role doesn’t need to carry the weight of the next twenty years,” she says. “For some people, the first move becomes the start of a long and successful second career. For others, it’s a valuable first landing, and that’s fine too.”

Jenny also works with veterans who are already well-established in civilian life and are asking a more refined question: not whether they can succeed outside the military, but what they want next. “They’ve proved themselves in a new environment. They’ve built civilian credibility. They understand the market more clearly. Now they’re ready to make a more ambitious move, and that’s not a sign the first transition went wrong. Careers evolve.”

Her benchmark for any move, first or fifth, isn’t “is this perfect forever?” It’s simpler than that: “Does this move make sense for the direction I want to build? That allows for ambition without demanding certainty.”

ABOUT JENNY ROBERTS
Jenny is a RAF veteran who went on to build a 13+ year career in civilian recruitment and hiring, working with major employers including Rolls-Royce, BAE Systems and the NHS. That dual perspective – having made the transition herself, and having sat on the hiring side of the table for over a decade – shapes how she coaches: she knows what employers are actually weighing up when an ex-Forces CV lands on their desk, because she’s been the one making that call.

ABOUT MILITARY TO MARKET
Military to Market is Jenny Roberts’ four-month, one-to-one coaching programme for Service leavers who want clarity on where their military experience fits, what level they should be targeting, and how to position themselves for the civilian market whilst optimising their resettlement window.

Clients leave knowing where they fit into the civilian market, at what level, and how they’re going to get there.

Find out more or book a discovery call: www.jennyrobertscoaching.co.uk/military-to-market