I've Coached Hundreds of Leaders Through Transition. Here's What Mine Actually Looked Like.

Most transition content is written for the leader who didn't choose the exit, the restructure, the merger, the tap on the shoulder. That leaves a gap for the leader who did choose it, and still found the transition harder than expected. I want to walk you through what that actually looked like for me, because I know I'm not the only one who's felt it.

When the shape of my role changed, I didn't need convincing. It was the moment to execute a decision I'd already been building towards: not to chase a passion project, but to do serious work with people who are genuinely ready to work or live differently, while I still have the time and energy to build something that lasts.

One thing worth mentioning here: a planned exit and one that happens to you carry different practical challenges, but strikingly similar emotional ones. I hadn't experienced that overlap directly, until I did.

The Planning Was the Easy Part

By the time I stepped away, this wasn't new ground. I'd been coaching alongside my corporate roles for close to twenty years, held ICF PCC accreditation and a Master's in Strategic Organisational Development, and sat on advisory boards across hospitality, education and coaching. Two decades leading teams, P&L and commercial outcomes and coaching both inside and outside organisations had given me a body of experience and a network I knew translated into genuine value for the leaders I wanted to work with.

I had a business plan, a name (Worth Coaching), and a clear view of who I wanted to serve. Strategically, I was ready. Financially, I'd modelled it out. On paper, this was about as low-risk an executive transition as a senior leader can make.

What I hadn't modelled was the six months that followed.

What the Business Plan Didn't Cover

My days used to be full of back-to-back meetings. I don't miss the ones that had no real relevance to my work. What I do miss is having a team to lead, I enjoy that part of leadership, supporting people and pushing a group toward a result. Board papers became business proposals instead, and there was no one else's calendar deciding what my day looked like. I'd built the freedom I wanted. It felt nothing like how I'd been operating, or conditioned to operate, inside corporate life.

Some days that felt good. other days it felt lonely, and staying motivated and focused was harder than I expected in that gap. On the tougher days I found myself wondering if I was still relevant, and questioning whether I still had the hunger to drive this on my own, without a title or a well-known organisational brand behind me, and how do you push through the assumptions people quietly make about you once you're no longer inside one of the big organisations. The isolation could creep in, especially working from my garden office with clients on Zoom and the dog for company.

As a coach, I told myself I should already know how to work through this. I did, with the advisory board I'd built around myself early. Knowing the theory and living the actual gap between who you were in the role and who you are without it are two different things entirely, and that gap is where most of the leaders I now work with get stuck. Not in the planning, which they're usually good at, but in the identity work underneath it, which nobody ever taught them to do. Here's what that lived executive transition, combined with coaching leaders through their own, taught me.

Three Things I'd Tell the Version of Me Who Was Six Months From Leaving

Build the support before you need it, not after. I'd spent my career being the person others relied on for clear thinking. I hadn't built the same for myself. I now put a genuinely independent sounding board, someone with no stake in my decision, in place before any significant transition, not during the wobble that follows it.

Expect the identity cost, even when the decision is right. Leaving a title you've held for years costs something, regardless of whether you chose it. Planning for that cost the way you'd plan for a financial one saves you from being blindsided by it.

Don't confuse busy with clear. In those first months I could easily have filled the diary with activity: meetings, calls, anything that recreated the old rhythm. That activity would have felt like progress.however it would have delayed the actual work, which was deciding what I wanted this chapter to be for, not just what I wanted to fill it with.

Why I'm Telling You This Now

I see two groups of leaders most often in September and October: those weighing a genuinely planned exit, a board pivot, a retirement, a move into portfolio or advisory work, and those still catching up on a senior leader's career change they meant to make earlier in the year.

If that's you, the pattern I see repeatedly is this: the strategic plan is usually in reasonable shape. The part that gets skipped is the one I skipped myself, building support and doing the identity work before the diary empties, not after.

That's exactly why I'm building a small, curated group program for experienced professionals who are serious about thinking differently about their next chapter, working through the same territory I had to work through myself, alongside people who understand what a professional career or life change actually costs. Watch this space. Join the waitlist

That same groundwork applies whether the transition ahead is retirement, a career pivot, or simply the sense that something needs to change: the identity questions don't shrink just because the shift looks different on paper. If anything, the less external structure you have to lean on, the more they matter. I run individual coaching for senior leaders navigating exactly that, retirement included. (Book a confidential conversation)

If you want the practical framework first, before any conversation, The Transition Playbook covers the same ground: values, energy, mindset and intentional planning for what's next. (Grab your copy here)

I hope this story lands with anyone who's planning this kind of transition, or already living inside one. You don't have to do it alone.

Janette Illingsworth is the CEO and Founder of Worth Coaching, an executive coaching and leadership advisory practice working with senior leaders, executives and founders navigating high-stakes transitions and organisational change. Based in Sydney. ICF PCC coach. Gallup-certified strengths coach. 30+ years of leadership experience across sectors, including senior talent and organisational development roles within ASX-listed corporate Australia.