How to Explore Your Interests and Find a Career Path That Fits

Last week, we talked about finding interests and possibilities during a life transition. But what happens once something catches your attention?

Maybe you have an interest you cannot stop thinking about. But then comes the big question: Is this just a passing fancy? A hobby? A side gig? A new career direction? Could it even be part of my purpose?

It is easy to put a lot of pressure on that interest. Here is the good news: you don’t need to decide yet. You are allowed to be curious before you commit.

An interest does not need to immediately become productive, profitable, or permanent to be worthwhile. Exploring it is how we learn whether it offers energy, meaning, connection, skill-building, flexibility, or simply delight.

Try an Interest Experiment

Think of this as gathering clues, not making a lifelong decision. 

1. Create a “what matters list” 

Before you decide whether a particular interest is worth pursuing, get clear about what helps you thrive.

What matters to you in the way you spend your time, whether that is in work, a hobby, a volunteer role, or a possible side gig?

You are not trying to create a perfect checklist. You’re simply noticing the environments, rhythms, and values that help you feel more like yourself. 

Your list might include:

• The amount of flexibility or structure you want

• The amount of interaction: Working alone, with others, or a blend of both

• The location you prefer: Remote, in-person, or hybrid setting

• The financial aspect: whether income is required, optional, or not a factor

• The opportunities for creativity, movement, problem-solving or service

• The learning curve and your willingness to pursue education or training

• The connection to your values, strengths, or a cause that matters to you

• The time, energy, and financial investment you are able to make right now

2. Name your interests & pick one to explore

Look back at your notes from the Best Life Exercise, last week’s interest questions, and any career exploration tools you have completed. If you haven’t completed these earlier reflection activities, you can read about them in last week’s post.

What ideas, activities, topics, or roles keep catching your attention? 

Choose one interest that you are curious enough to explore. 

Not the one you think you should choose. Not necessarily the one that seems most practical. Just the one that makes you think, “I wonder what that would be like?”

3. Gather real-life information 

A quick online search can be helpful, but real-life information is often where things begin to feel clearer. Google can tell you what a job title means, but a real person can tell you what their Tuesday afternoon is actually like. 

Talk with someone who works in the field, volunteers with an organization, or participates in a community you are curious about. You might also attend a meetup, take a class, volunteer once, or join an event.

Not sure whom to ask? Tell friends and family what you are exploring and ask whether they know someone connected to it. You can also search your alumni network, LinkedIn, or local, state, and national organizations related to the field or cause.

If you have a chance to talk with someone, you might ask:

• What does a typical day or week look like for you?

• What do you enjoy most about this work, cause, or community?

• What is more challenging or different than people might expect?

• How did you get involved?

• What strengths or qualities are especially helpful?

• If you were just starting out, what small step would you recommend?

4. Take time to reflect

After you gather information or try something new, pull out your “What Matters” list and look for matches and mismatches.

Did this role, activity, organization, or community offer some of the conditions that help you thrive? What felt aligned with your values, strengths, needs, and current season of life? What felt out of alignment?

Then decide on your next small step. If you noticed that this interest seems to fit what matters to you, you may want to continue exploring. Perhaps that means another conversation, a class, a volunteer opportunity, or a slightly bigger experiment. 

If it feels like a poor fit, you can set it aside for now and turn your curiosity toward a different interest.

What If Exploration Feels Discouraging?

Exploration does not always feel exciting. You may feel disappointed when an interest, role, activity, or community does not turn out to be what you hoped. It can be hard to discover that something you imagined might be a good fit does not align with your values, needs, energy, or life right now. Sometimes exploration leaves you with more questions instead of clear answers.

If that happens, try to meet yourself with self-compassion. First, notice the disappointment without judging yourself for having it: “This is hard. I was hoping this would feel like a better fit.”

Then remind yourself that you are not alone. Everyone encounters dead ends, mismatches, and uncertainty while figuring out what comes next. This is part of being human, not proof that you are doing it wrong.

Finally, offer yourself some kindness. You might speak to yourself as you would a friend: “It makes sense that I feel disappointed. I am proud of myself for being curious and taking a step. I do not have to have all the answers today.”

Instead of labeling the experience a failure, consider what it taught you. A mismatch can still be meaningful information. It helps you refine your “What Matters” list, choose a more fitting next experiment, and move a little closer to something that feels right for you.

For more ideas about practicing self-compassion when your inner critic gets loud, you can read my earlier post, How to Stop Beating Yourself Up.

Exploration may leave you with more questions instead of clear answers, but each experience can still offer a useful clue about what to explore next.

Join the Conversation

What is one interest you would like to explore more deeply right now?

Or, if you have explored an interest that did not turn out the way you expected, what did it teach you?

Share in the comments. I would love to hear what you are exploring, and your experience may encourage another reader who is figuring out what to try next

Need Support?

If you’d like personalized support while navigating a life transition, email me at dianna@collierclan.net for a free consultation.