Day: September 20, 2025

• Ashley Jablow is a career coach who helps mid-career professionals navigate career transitions.
• She says clients may feel stuck due to financial obligations and caregiving responsibilities.
• Her four-step process includes self-discovery, iterative action, and more.

This as-told-to essay is based on a conversation with Ashley Jablow, a 44-year-old career coach based in Richmond, Virginia. It’s been edited for length and clarity.

Most clients come to me because they feel stuck in their careers. They’ve picked up their heads at 30, 40, 50, or beyond and realized that the life and career they chose for themself at 20 no longer fulfills them.

As a career coach who helps mid- and senior-career professionals navigate career transitions, I see that these changes later in life aren’t always as easy as they might be if done earlier. Many of my clients have constraints and existing structures created by financial obligation, caregiving responsibilities, existing careers, and more.

My job is to help people clarify what they want and take actionable steps toward achieving their goals. These are the four steps I take my clients through who want to pivot their career after 40.

Step 1: Discover who you are right now

Although your instincts might be to rage-quit your current job or jump right into solution mode, it’s important to take a step back, open your field of vision, and get curious about who you are at this point in your life.

If asking deep, probing questions like, “Who am I?” is uncomfortable, you simply need to become curious about what topics you’re drawn to — what creates goosebumps and excitement.

I think a lot of mid-career folks don’t spend enough time feeding the fire within them and pursuing things simply because they excite or inspire them.

The purpose of this exercise isn’t to figure out your next career move but to ignite a curiosity and sense of wonder about what makes you who you are. For example, I love stationery supplies like pens, brushes, and notebooks. That doesn’t necessarily mean I should become a stationery designer.

The discovery phase is also about looking outside ourselves and seeing what we’ve missed while existing in our insulated bubbles. For example, look at how the job market has changed and how recent advancements, like AI, might change the opportunities that are available to you.

Step 2: Define your constraints

Next, it’s time to pause and set parameters for the rest of your brainstorming. Consider dealbreakers, criteria for success, and current constraints such as location, salary, time commitment, etc.

Though it may feel like your existing life structures constrain you, I see identifying constraints as a helpful tool for acknowledging your reality and setting criteria accordingly.

Step 3: Imagine your dream life

Using your imagination will be your greatest tool for coming up with creative solutions to your constraints.

This phase is all about being broad and exploratory. We should ask ourselves, “If I had a magic wand, where would I go, and what would my life look like?”

This can involve making a vision board or writing a vivid depiction of your future. Imagination isn’t just for five-year-olds on the playground, and it’s one of the most underutilized tools for creative problem-solving.

Step 4: Iterate to reach your goal

Once you’ve considered your near-term constraints and long-term vision, you might identify a potential goal or area of interest.

For example, a client might decide to quit their job and go to business school. But rather than taking radical action, I’d advise them to consider the smallest, fastest, and cheapest ways they could test if this is a worthwhile decision. This is what I call iterative action.

They could speak to a peer who went to business school and ask them questions about their experience, buy an “Economics for Dummies” book to see if the topics interest them, or even sign up for an online course, like an MBA crash course, to get a sense of what it might be like.

The cool thing about taking iterative action is that the more we take small steps, the more we learn about ourselves, and the less risky a career pivot becomes. We might even find that we’re building confidence in our ability to make good decisions and follow through on our goals.

Do you have a story to tell about changing careers after 40? If so, please reach out to the reporter at tmartinelli@businessinsider.com.