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Blog Anna Careers Coach Thumbnail

I Hired A Career Coach, Here’s What Actually Surprised Me

19/08/2026
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Career & Personal
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Posted by Joe Winfield

I didn’t know what I wanted next. Turns out that was exactly the right reason to get help.

A few months ago, my job was winding down. I knew it was coming as the programmes we were working on had a natural end and I’d seen it on the horizon for a while. So when the time came, I wasn’t caught off guard. I just wasn’t sure what came next.

I’d been in web design, development and UX for over 14 years. I knew what I was good at. I just wasn’t entirely sure what I actually wanted anymore, and those two things, I’ve learned, are not the same.

I’d heard of career coaches but honestly didn’t know what they did. Then one day, I saw a recommendation on LinkedIn from a former client for Anna Cieslowska, a career change coach and founder of Anna C. Career Glow, and thought, why not? The job market is tough right now. Going in blind and landing somewhere that could burn me out in six months wasn’t an option. So I got in touch.

Here’s what I didn’t expect.

The First Few Sessions Weren’t About My CV

If you’d asked me before starting what career coaching involved, I’d have said CVs, LinkedIn, portfolio, cover letters. Optimising everything and getting it out there. That made sense to me.

So I was genuinely surprised when the first three sessions had nothing to do with any of that.

Instead we talked about me. My values. What energised me. What had been quietly draining me for years without me fully naming it. What I’d been tolerating in roles because I was good at the work, even if the work wasn’t quite right for me.

It felt almost counterintuitive at first. Shouldn’t we be doing something? But that groundwork turned out to be the most valuable part of the whole process, because everything that came after was built on it.

The Phrase That Changed Everything

Halfway through the programme, Anna introduced me to a term I’d never heard before: individual contributor.

Someone who works hard, is a key team player and communicates well – but whose primary value is in the craft, not in managing clients or running meetings all day.

That was me. That was exactly what I wanted. I just didn’t have the words for it.

Once I had the words, everything clicked. I stopped looking at broad design job listings and started filtering properly. A lot of the roles I’d been considering, and probably would have applied for, I realised weren’t the best for me.

Knowing that in advance felt, as Anna put it, freeing. And it really was.

What The Process Actually Looks Like

It was more structured than I expected, and that structure was genuinely useful. Here’s what we worked through together:

  1. Energisers and drainers: identifying what gave me energy at work and what quietly wore me down.
  2. Top values: pinpointing what actually matters to me, not just what I thought should matter.
  3. The career wheel: a structured exercise for mapping and scoring different areas of work and life. This is where a lot of things crystallised.
  4. Job role names and options: reviewing what roles actually exist that match what I’d uncovered about myself. This is where “individual contributor” entered my vocabulary.
  5. Platforms: figuring out where to actually look, because not all job boards are equal depending on what you’re after.
  6. Optimising everything: CV, cover letters, email templates, LinkedIn, portfolio. This came later than I expected, and was better for it!
  7. Application tracker: keeping a proper record of applications and contacts so nothing slips through.
  8. Mock interview prep: Running through real interview scenarios so that when the moment comes, you’re ready for it.
  9. Weekly schedule: building a day-by-day routine to stay consistent and confident without feeling hopeless.

Worth noting: while this was the structure I followed, Anna’s Aligned Career Change Method is deeply personalised. Every engagement is 1:1 and tailored to where you are and what you actually need.

Anna and I sat down and talked through my experience on camera if you want to hear it in our own words rather than a bullet list.

What I’ve Been Doing Since

With a clearer picture of what I’m looking for, I’ve been using the time between applications well. Upskilling in areas that show up consistently in the roles I actually want. Talking to people already in those jobs – asking what tools they use, what they’d want to see in a portfolio, what gaps I should be filling.

It’s a better use of time than doom-scrolling job boards, and it’s been genuinely energising rather than draining.

Would I Recommend It?

Yes. Particularly if you’re in the same position I was – not in crisis, but not fully sure either. The job market is different now. Harder, noisier, and full of roles that sound right until you’re six months in and wondering how you ended up there again.

If you’re unsure whether coaching is for you, Anna puts it better than I could on her site: annac-careerglow.ie

And my advice? If you’re on the fence, that’s probably your answer. Just do it.

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