Career Change: Finding Your Path with the Help of a Coach

You have a large international work experience. What inspired you to become a coach?

For as long as I can remember, I’ve been curious about how things work. That curiosity led me to study engineering and start a career in the manufacturing industry. A few years into my role as a project manager, I realised that what truly fascinated me wasn’t the technical side but the people side – understanding what motivates them, why they behave the way they do, and how I could help them achieve more. That insight drove me to take on leadership responsibilities, where I could expand my impact. After seeing strong results, my manager introduced me to coaching, believing it would be a natural fit, and he was right.

Since completing my training and opening my coaching practice in 2018, I’ve been continually inspired by what people can achieve with determination, courage, and the right support. The spark in their eyes when they let go of fear, discover what they truly want, or unlock a new idea is a moment I’m so grateful to share with my clients.

Even in my early pro-bono coaching experiences, I saw clients make meaningful progress. Those first results showed me the power of coaching and convinced me that, if I pursued it seriously, I could impact many more lives. Working across different cultures taught me how universal, yet personal, people’s motivations are, and this made coaching even more meaningful to me.

What are the most common challenges for people looking at a career change?

You can categorise them in two groups, although only one is where the coaching magic really happens. The first group I call “outer logistics” and the second one “inner battles”.

The outer logistics are things that can relatively easily be researched and solved either on your own if you put your mind to it or with getting help from your network or other people that are where you want to be. These include questions such as: where can I learn the skills? How do you start a business? Is there a market? How do I raise the starting capital?

Those are all good and important questions, but in today’s age of information, the answers are “out there”, you just need the right reasons to go and find them. That leads us to the second group, the inner battles.

The main reason more people are not doing what they really aspire to do is not because of a lack of information, or skills, it is because of their inner battles. This is where working with a coach can truly be a game changer.

Questions that often come up in the inner battle category include: what if I fail? Can I really be successful? Am I smart, young, old, experienced, … enough? What will people think?

“If you keep asking disempowering questions, you will keep getting disempowering answers” – Tony Robbins

A coach will help you ask the right questions, see past your self-limiting beliefs and get unstuck.

Inner battles are why many people know what they should do, but few take action until they have support.

What are the signs the now might be a good time to change the course of your career? 

From my experience, we all go through cycles in life. Some have longer cycles, some shorter, but almost inevitably you will go through different phases in your professional life that resemble the seasons.

• Spring – the start of a new position or a new company. You feel excited, you are learning and growing. Your energy levels are high.
• Summer – You have learnt the ropes, and you are now very productive. You are good at what you do, you start getting rewards and your energy levels are still high.
• Autumn – Your efforts have paid off, you are experienced, and tasks that once were hard are now easy. Your energy levels are strong and steady, even if slightly lower.
• Winter – You start wondering what’s next, as nothing surprises you anymore. You are no longer growing, and your energy is low.

Recognising yourself in Winter doesn’t mean you must change careers, but it may be the right time to explore your options towards a new cycle.

Another sign that might point towards a potential career change is if you find yourself longing for something else regularly. Some people call it dreams or fantasies, but sometimes it is worth checking in with yourself: Am I being honest with myself? What do I really want in life? What is truly important to me?

The first two are internal factors, but it is also worth considering external ones: a declining industry, a product becoming obsolete, or the rise of AI can all signal that it is time for a career change, whether you are ready or not.

What does “transition coaching” means in practice and how does it differ from other types of coaching?

Transition Coaching is used mainly in the outplacement industry, where the services of a coach support people who have been laid off to transition into their new career.

Having to change jobs can be an emotionally charged experience, bringing both outer logistics and inner battle challenges.

The main difference is that the scope of a transition coaching session is much more dynamic, because changing jobs implies a multitude of different aspects that may be addressed during the process.

For example, when I do performance coaching with a client, they will usually have a specific goal in mind that becomes the golden thread throughout the sessions. They are prepared to work for it, and they initiated the process themselves. In transition coaching, the central focus is “land a new job”, but how that translates for different people can vary greatly (e.g. self-esteem, limiting beliefs, upskilling, strategizing, goal setting, etc.).

Often, you first need to work with the client on managing their emotions, changing their story, and rebuilding self-esteem before they are ready to work toward the ultimate goal of finding a new opportunity. Helping them reframe the situation into an empowering one requires a different set of tools and techniques.

How does working with a coach usually starts and what to expect from the sessions?

The first step is always to build a relationship. It is critical in any type of coaching and is the foundation of success.

The coaching process is not always pleasant. As coaches, we hold a mirror to the client, keep them accountable, point out dissonances, and ask them to look deep inside themselves. It requires a strong bond and a high level of trust to work at that depth.

Most coaches offer a “chemistry session” or “intro session” free of charge before the real work begins. In my opinion, this is crucial. I like the term “chemistry”, because it really reflects whether the coach and the coachee connect on that level. Not everyone feels comfortable with everyone, and that’s OK. As a client, you want to make sure you feel completely comfortable with the coach you choose. If you don’t, say so and find someone else. The coach will understand, checking compatibility is the sole purpose of those sessions.

Every client, session, goal is different, but if I were to point out a few things on what not to expect, they would be these:

1. “The coach will tell me what to do” → No, we won’t. A coach is not a professional in your specific area of expertise, nor do they know all your circumstances. Instead, we truly believe that you have everything it takes to find the answer, and we help by asking questions to create more awareness around your possibilities. The decision, however, is yours to take.
2. “The coach will do most of the work” → The client will do the heavy lifting. The coach will ask questions that hopefully trigger new ideas or explorations, but it takes effort on the client’s part to work through them.
3. “The coach must be an expert in my field” → Actually, no. It is often better if they are not. The job of the coach is to ask questions that make you think. Not knowing your field ensures the coach doesn’t bring biases.

A coaching engagement is based on partnership, and as such, expectations are discussed upfront and revisited throughout. Openness is the key.

What are the roles of the coach and the client in the career change process?

The coach – coachee relationship is defined by the ICF as “Partnering with clients in a thought-provoking and creative process that inspires them to maximize their personal and professional potential.”

In practice, this means the process is client-centered: the agenda of the session belongs to the client. The client is responsible for defining the goal for the session, but also has the right to change it at any time if new priorities emerge. The coach always supports the client’s agenda.

It also means that the partnership is forward-looking. The coach’s role is to focus the conversation on growth, solution and possibilities. Clients often want to share long stories about their situation, but the coach helps to refocus on learnings and growth, even if that feels uncomfortable. It also means the client needs to be willing to play full out and be honest with the coach, but most importantly, with themselves.

Finally, it means empowering the client to take action. Here again, the coach has a critical role to play. By helping the client raise their self-awareness and generate their own strategies, the coach helps eliminate barriers to action, both internal and external.

What type of practical tools or exercises do you use to help clients get clarity on their goals and values?

Every person needs a specific approach, but over the years, a few tools have become my go-to, often because of their simplicity and impact.

The 5 Why’s

This comes from the automotive problem-solving industry, but I find works wonders in coaching. The tool is simple: ask “why” five times to get to the root cause of an issue. In coaching, it helps peel back the layers and access the deeper reasons of why, for example, someone would want to change career. On the first “why,” someone might say they don’t like their boss or they want more money. But that’s just the surface. If you keep asking, you might discover they lack purpose or fear becoming obsolete. Once the real reason is clear, the work can truly begin.

Future pacing

This tool helps create clarity for the client’s goals. If they are unsure of what they really want, future pacing will let them imagine a future without any restrictions, where they are free to do whatever it is they want. Surprisingly enough, although we are all capable of doing this on our own, most are afraid to go there alone. Done in a coaching session, it brings out what matters most and sparks deeper conversations about what a new career might look like.

5-cents words

Many times, I hear visions that sound like Shakespearean essays rather than strong emotional goals. There are two main problems with that: you can’t remember them, and they don’t emotionally pull you forward. The tool is simple: use cheap, emotionally charged words that speak directly to you. Everyone is different, everyone has words that will trigger an emotional response. For some it may be “to impact”, for others “to shape”, or “to create”. The words themselves don’t matter, what matter is that the goal is short enough to remember, and stirs something inside you. If I wake you up at night and ask: “what’s your goal?”, I want you to tell me in a blink and with excitement, even if it’s 2am.

Can you bring a few examples where coaching has helped people bringing significant change in their career?

Everyone enjoys a transformation story where the protagonist goes from one extreme to the other. They are fascinating, but they can also feel intimidating, triggering thoughts such as, “this could never happen to me”, or “I don’t think I’m that kind of person”. The good news is: it doesn’t have to be a dramatic transformation.

Imagine you are piloting an airplane – your career – with a flight plan from Tallinn, Estonia to Vancouver, Canada. For some reason, you adjust your course just a few degrees south. At first, everything looks the same. The horizon hasn’t changed, the sky is still clear. But by the time you cross the ocean, you’ll end up in Seattle, in the U.S. That’s a whole different destination! For most of my clients, that’s exactly what happens: just a small shift in direction completely transforms where they land in their careers.

Recently, one of my clients, a seasoned IT manager, felt he needed a change, but had no clear vision of what it should look like. During our work, we explored his personality, what energised him, what drained him, his purpose and values, until he had his “Aha” moment: he didn’t want to leave his company or his industry. What he was missing was creativity and time for deep, independent work. He realised he had become a manager years ago to support his family, not because he enjoyed it. Years later, with his family settled, he could return to what he truly loved, programming. A small shift, with a huge impact on his wellbeing and career.

Another client felt stuck and had been passed over several times for a promotion. She was growing resentful and was contemplating leaving a company she ultimately liked. Her manager wisely suggested coaching. After clarifying her ambitions and drivers, we mapped the gaps between where she was and where she wanted to be. She designed a strategy to systematically close those gaps. After a few months working on her image, skills, and communication, a new position opened in her company, and she was promoted.

What type of results can typically be experienced right from the first session?

People who come to coaching usually feel stuck in their circumstances.

I like to use this metaphor to illustrate the first session. Imagine you need glasses, but you keep delaying buying them. You adapt to your blurry vision and almost forget what clarity looks like. Then, one day, you finally get glasses, and you are absolutely amazed by the sharpness, the colours and the details you can suddenly see. That’s what coaching often feels like. The first session is an eye-opener: clients leave with new perspectives, even before setting long-term goals.

Other results after the first session vary, but the most common are a clearer goal, renewed energy or ambition, the first steps of an action plan, increased self-esteem, and almost always, deeper self-awareness.

If someone is standing at a career crossroad, what would be your three main recommendations?

If I had to share three pieces of advice with anyone standing at a career crossroads, they would be these:

1# Don’t rush.

Take the time to understand why you’re considering a change. Are you running away from something (like a difficult boss, low pay, or boredom) or are you running toward something (such as an exciting industry, a new role, or an inspiring mission)? Reflecting on this difference will help you ensure that your decision is aligned with what truly matters to you.

2# Be prepared.

A career change often involves a gap between where you are now and where you want to be. Developing self-awareness will help you identify those gaps – whether in skills, experience, or visibility – and create a concrete plan to close them. Preparation won’t guarantee you the job, but it will dramatically increase your chances of success.

3# Get support.

Making a career shift can feel overwhelming when done alone. Working with a trained coach can give you perspective, clarity, and a safe space to reflect on what you really want. Coaching tools are designed to uncover blind spots, challenge assumptions, and help you reconnect with your values. That support can save you years in a role that no longer serves you or prevent you from jumping into the wrong opportunity for the wrong reasons.

Conclusion

A career change doesn’t have to mean turning your life upside down. Sometimes it’s just a small shift – a few degrees in a new direction – that leads you to a completely different and more fulfilling destination. Coaching provides the tools, space, and support to make that journey with clarity and confidence.