The Uncomfortable Side of a Career Pivot

What I Learned From Being the Least Knowledgeable Person in the Room

A career pivot can be one of the most exciting, challenging and terrifying things you can do.

Particularly when you’ve been working in an industry for a couple of decades.

After 20 years in a particular field, you develop a certain level of confidence. You know your craft. You know your subject matter. You understand the language, the systems and the people. You become a subject matter expert.

You know when to speak up, when to challenge something, when to offer an opinion and when to trust your experience.

And then, sometimes, you deliberately step into a space where you know very little.

That was me last year.

Stepping into unfamiliar territory

For the past 20 years, my career has largely been in regional development, community and the arts and cultural sector work that I genuinely love and care deeply about.

I’ve worked across community engagement, stakeholder relationships, project management, strategy, leadership and complex projects. Over time, I built up a strong base of experience and, importantly, confidence.

I knew my stuff.

Then last year, I took on a project management role in the planning space.

Planning was new territory for me. I didn’t have technical expertise in planning, and I was completely transparent about that from the beginning. There were no surprises for anyone.

I wasn’t brought into the role because I was a planner.

I was brought in because of what I could bring: strong community and stakeholder engagement experience, relationship management, project management and the ability to work with people across complex and sometimes challenging environments.

I was excited about the opportunity.

I’ve always believed that continuing to learn and develop your skills is one of the things that keeps us fresh and engaged in our work. Learning something new gives us the opportunity to stretch ourselves, challenge what we think we know and discover capabilities we didn’t know we had.

What I didn’t anticipate was just how uncomfortable it would feel to suddenly be the person in the room who knew the least.

When expertise disappears, confidence can disappear with it

For the first time in a very long time, I was sitting in meetings where I didn’t understand the terminology.

I didn’t know the processes.

I didn’t have the technical knowledge to contribute meaningfully to some of the conversations.

And that was uncomfortable.

More uncomfortable than I expected.

My engagement experience could get me across the line in terms of working with people, building relationships and managing the project, but I needed to understand enough about planning to actually manage the project well.

There were plenty of moments where I had to ask questions that probably felt very basic.

There were conversations where I had to sit back and listen rather than contribute.

And there were times when I left a meeting thinking, I really should know more than this.

But slowly, something changed.

I started asking more questions.

I started understanding the terminology.

I began connecting the dots.

I found people who were generous enough to explain things to me.

And I realised that I didn’t need to become the planning expert in the room.

I needed to become good enough at understanding the subject to do my job well and to know when to draw on the expertise of others.

After nearly 18 months on the project, I can confidently say I know a lot more about planning than I did when I started.

But more importantly, I learned a lot about navigating the discomfort of being a beginner again.

So, what did I learn?

1. Be transparent about what you don’t know

There is no point pretending to have expertise that you don’t have.

I was upfront from the beginning that planning wasn’t my area of technical expertise. That transparency created space for people to understand where I was coming from and, importantly, to help me.

If you don’t know something, ask.

If you don’t understand the terminology, ask.

If you need something explained again, ask.

There is enormous value in being willing to say, “I don’t understand that, can you explain it to me?”

People are often far more generous with their knowledge than we give them credit for.

But you have to give them the opportunity to share it.

2. Remember why you are in the room

This was probably the most important lesson for me.

When you’re surrounded by people who know more than you about a particular subject, it is very easy to focus on what you don’t know.

Instead, I had to remind myself why I was there in the first place.

I wasn’t hired to be the planning expert.

I was there because I had more than 20 years of experience in other areas that were valuable to the project.

I could bring strong relationship management and stakeholder engagement skills.

I had experience leading complex projects.

I knew how to navigate difficult conversations.

I understood community.

I knew how to bring different perspectives together.

I knew how to build trust.

I knew how to manage competing expectations and work through conflict.

Those skills didn’t disappear simply because I was working in a new sector.

In fact, they became even more important.

When you’re feeling out of your depth, remind yourself:

What did they hire me for?

Then lean into that.

3. Get curious rather than trying to look clever

There is a real temptation, particularly when you’re an experienced professional, to feel like you should already know.

But curiosity is much more useful than pretending.

Ask questions.

Listen carefully.

Notice how people approach problems.

Ask subject matter experts how they think about an issue.

Find out why something is done a particular way rather than simply learning what is done.

Curiosity turns the discomfort of not knowing into an opportunity to learn.

And, frankly, it makes the whole experience a lot more enjoyable.

4. Find the people who know what you don’t

You don’t need to know everything.

You need to know who knows.

One of the great advantages of working in a multidisciplinary environment is the opportunity to draw on different people’s expertise.

I learned to rely on the people around me who had the technical knowledge I didn’t have.

That isn’t weakness.

That’s good project management.

The ability to recognise the expertise around you, bring the right people into the conversation and create an environment where people can contribute their knowledge is a skill in itself.

5. Be comfortable being uncomfortable

This is probably easier said than done.

When you’ve spent years building expertise, being a beginner again can feel like a loss of status.

You go from being the person people come to for answers to being the person asking the questions.

That’s a very different feeling.

But discomfort doesn’t necessarily mean you’re in the wrong place.

Sometimes it means you’re growing.

A career pivot doesn’t mean leaving your experience behind. It means taking that experience into a new environment and discovering how transferable it really is.

6. Don’t underestimate the value of transferable skills

One of the biggest things this experience reinforced for me is that our careers are rarely as linear as we think they are.

We tend to define ourselves by our industries or job titles.

I’m an arts professional.

I’m a planner.

I’m a project manager.

I’m a communications specialist.

But underneath those labels are capabilities that can travel with us.

Relationship building.

Communication.

Leadership.

Problem solving.

Negotiation.

Strategic thinking.

Project management.

Facilitation.

Conflict resolution.

Adaptability.

Community engagement.

These skills don’t belong to one industry.

They belong to you.

And sometimes a career pivot is an opportunity to discover just how valuable those skills are somewhere completely unexpected.

7. Keep your sense of humour

This one matters more than we probably admit.

There were plenty of moments during this project when I had to laugh at myself.

You can’t know everything.

You can’t understand everything immediately.

And sometimes you are going to ask a question that, in hindsight, feels ridiculously obvious.

That’s okay.

We’re all learning something.

A little humility and a good sense of humour can make the process much easier.

The unexpected gift of being the least knowledgeable person in the room

Looking back, I think one of the most valuable parts of this experience was being reminded what it feels like to learn from the beginning.

When you’ve been an expert in your field for a long time, it’s easy to become comfortable.

Comfortable in your knowledge.

Comfortable in your networks.

Comfortable in your confidence.

And there is nothing wrong with that.

But there is also something incredibly energising about being challenged again.

Being curious again.

Having to listen more carefully.

Having to ask questions.

Having your assumptions challenged.

And discovering that you can learn a completely new body of knowledge—even after 20 years of working in another field.

I didn’t become a planner.

And I didn’t need to.

But I became a much better project manager because I was willing to learn enough about planning to understand the environment I was working in.

And perhaps that’s the real lesson of a career pivot.

You don’t have to start again.

You take everything you’ve learned with you.

You take your experience, your relationships, your judgement, your skills and your perspective.

And then you add something new.

Sometimes that process is exciting.

Sometimes it’s terrifying.

And sometimes you’re sitting in a room thinking, I have absolutely no idea what these people are talking about.

But if you’re willing to stay curious, ask questions, lean into what you do know and be open about what you don’t, that uncomfortable space can become one of the most rewarding places to be.

Because growth doesn’t always feel like growth.

Sometimes it just feels like being the least knowledgeable person in the room.

And maybe that’s not such a bad place to be.