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Hi there, it’s Jill!
A common question my clients ask when considering a career transition is:
How will I know if I’ll actually like the new job once I get there?
Career move isn’t just a change in title, it can impact your momentum, your confidence, and sometimes even your lifestyle.
Believe it or not, the answer often lies closer than we think: in your current role. The real question becomes:
How can I test run my next role before making the move, so I can make a more informed decision?
The good news is, when you approach this intentionally, you may also increase your chances of successfully making that transition.
Let’s dive in.
01
What You Don’t Like Is Just As Important
When it comes to career transitions, many guides suggest writing down what you like or enjoy doing as a way to discover your strengths.
In my experience, this works well for people who already have a clear sense of their interests and talents. If that’s you, that’s great! You can feel free to skip ahead.
But for those who don’t yet know what they like, or where their strengths lie, you’re not alone. Especially if this is your first time seriously considering a change, it’s very common to feel like you don’t have enough “data points” about yourself to make a confident decision.
So how do we approach this?
An equally effective, and often more accessible, approach is to focus on what you don’t like in your current role. Those are usually much easier to articulate.
There are two reasons why this is helpful.
First, by identifying what you don’t enjoy, you can avoid moving into roles with similar characteristics, reducing the likelihood of wanting to switch again.
Second, what you don’t like often reveals what you value, even if subconsciously.
For example, if you don’t enjoy being unclear about the impact of your work, you may value end-to-end ownership. If you don’t enjoy relying solely on convention to make decisions, you may prefer a more analytical, data-driven environment.
For many of us, it may take several transitions to fully understand ourselves. But each step adds to that self-awareness, making future transitions more intentional and easier to navigate.
Now, take a moment to think about the one thing you would most like to change in your next role, and let’s continue.
02
Reach for Adjacent Teams
Once you’ve identified what you don’t like, or conversely, what you’re looking for, the next step is to explore which roles or teams might offer that.
A practical place to start is with teams you’ve already worked with. Moving to adjacent teams is often easier, as there is usually overlap in domain knowledge, workflows, and existing relationships.
All of these give you a natural advantage compared to candidates coming from completely different backgrounds.
Networking with people in those roles is one of the most effective ways to deepen your understanding. If possible, try to speak with at least five people in that area. This helps you avoid relying on a single perspective and gives you a more well-rounded view.
During these conversations, pay attention to whether the role includes the aspects you’re trying to avoid, as well as what hiring managers are actually looking for in candidates.
03
Experiment It, Pay Attention To How You Feel
Once you’ve identified roles that interest you, the next step is to do some research. Resources like YouTube and even ChatGPT can be helpful in understanding what the role involves, the skills required, and whether it aligns with your long-term direction.
As your understanding becomes clearer, look for ways to gain exposure through your current role, especially if the transition is somewhat related.
Consider proposing one or two projects that allow you to build experience in that area.
This serves two purposes:
it gives you hands-on exposure
it allows you to test whether the role is a good fit without taking on unnecessary risk.
One question I often receive is:
What if the role I’m interested in is very different from what I currently do, and it’s hard to find overlapping opportunities?
That’s a very valid concern.
In these cases, it’s helpful to shift your focus from the specific subject matter to the underlying skillset.
For example, if you are a mortgage specialist looking to move into a product management role in credit cards, it may be difficult to work directly on credit card projects. However, if you’ve learned through networking that the role involves customer segmentation or campaign analysis, you can look for similar opportunities within your current domain.
In other words, focus on building transferable skills and demonstrating that you can apply them effectively. This gives you more flexibility in designing projects that strengthen your profile and make your transition more credible.
If the role you’re targeting requires a completely different skill set—for example, moving from data science to interior design—you may need to invest time outside of work to learn and build a portfolio.
Ultimately, the most reliable way to understand whether a path is right for you is to engage with it directly, and pay attention to how you feel. Does it energize you? Does it feel like a natural extension of your strengths? Or does it feel forced?
Final Thoughts
Self-awareness, information gathering, and experimentation form a powerful combination when navigating career transitions.
Together, they allow you to test your next step thoughtfully, rather than relying on assumptions.
And in doing so, you’re not risking what you currently have, you’re building toward what comes next with greater clarity and confidence
— Jill
Founder of Anchor Growth Newsletter

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