Thinking About a Career Change? Here Are 10 Questions to Ask Yourself First

It’s never too late.

By Kelly Krause
camille styles at home office desk_monthly routine

Last month I shared the top 40 things I’ve learned in (almost) 40 years and the responses were incredible. But the tip that got the most feedback was #24 where I shared: You’re never too late to do what you want to do. I hope you live your life constantly pivoting and evolving to inch closer to what lights you up. You’re never too late to make a career change, you’re right on time—your own time.

Many responded that they needed that reminder and permission to take a different path, and some shared they were relieved to hear someone almost 40 say that. I’m not sure about you, but that sentiment is ringing loud in my friend circle right now with many experiencing a season of transition, especially professionally.

Kimberly Snyder's morning routine, meditation, coffee, drink, books

Recently one of those friends asked, “How do you know when it’s time to leave your job or do something different?” I was really excited to answer. I crave change, love a pivot, and have never been one for complacency. While I know my advice is subjective, here’s what I shared for how I knew it was time for a change and the questions I’m using to gauge for future pivots:

1. I’m coasting vs. engaging. When I’m a passive participant in the role vs. actively engaged and interested in what I’m working on, that’s usually very telling. I know my excitement level can ebb and flow like anything, but when the feeling of coasting arises, I take it as a true sign.

2. I’ve been in the same role for years and no growth opportunities are on the horizon. I don’t mind staying at a company for years as long as I know there are opportunities to grow and learn within the business. And I don’t just mean taking on new clients or projects, I mean lateral growth to stretch my mind and skillset to the next level. When things aren’t moving, I tend to be the one to make the move.

3. Am I having fun? Fun is one of my top core values, so I check in with myself monthly and ask this question. I realize that every day isn’t a party, but, in general, does the work light me up and allow me to create space for fun internally and externally? By the way, this one question and prompt comes up for me a lot in dating, too. If I’m not having fun, it’s high time to re-evaluate the situation.

4. Compensation isn’t industry-standard. Pro-tip friends: learn what others are making in similar roles outside of your organization. Whether you’re asking them directly, or simply taking interviews to learn, it’s important to know. If you’re grossly underpaid compared to industry standards, you deserve better. Advocate for yourself (and your future!). I’m thankful my core group of friends feel comfortable sharing and we encourage each other to advocate and request our worth.

5. The business or company culture isn’t aligned with my values. I can’t imagine working for a company that didn’t value the same things I did. To represent a brand I don’t believe in would be living out of alignment and integrity. I’ve been in this situation in the past and oftentimes sharing a concern can lead to change, so don’t hold back, organizations need our voices to push and hold them accountable.

anine bing morning routine

6. How is my work valued? I love feedback and not just a “good job,” but a true quarterly review and clarity around how my work is making an impact on the business and areas of opportunity for growth and success. Years ago I worked for a laid-back company and boss. At the end of the year, I asked if we could carve out time for a formal review. His response was “You did well. I’ll let you know when you don’t.” That kind of response tells me I’m not valued, I’m a cog in the wheel, and he was lazy. All things that drove me to leave.

7. Other companies are capturing my eye with their innovation. I love staying connected and ears to the ground with what other brands are doing, especially as it relates to my role and line of work. On top of that, I’ve always found it beneficial to take coffees, learn more about their organization, and stay open and curious about what’s possible if I were to join their team. It’s how I’ve found many job opportunities, and I’ve noticed when my curiosity is piqued, it leaves me open to moving on.

8. Desire to try new things. When my desire to do something different is louder than my desire to stay, I know it’s time to move on. There’s not much more, I can’t dim that light and I usually need to act on it.

9. I’m not innovating. When my ideas are lackluster, and I’m not finding areas of opportunity to grow or expand, it usually means I’m lacking inspiration and motivation and it’s time to get curious about what could be next. Typically, traveling or attending a conference can spark ideas, but when I can’t maintain that momentum or new energy, I know it’s high time to look outside of my current role.

10. Am I holding myself back from living my dream? Ever sit at your computer and dream of doing something different? My question to you is: what’s stopping you from pursuing it? Back to tip #24: It’s never too late to do what you want to do. When I sat at my desk dreaming about a new role, I did everything I could to plant seeds and build a foundation to eventually pursue it. Curiosity, hundreds of coffee meetings, and “putting myself out there” paid off. Don’t hold yourself back.


These tips are of course personal to me and don’t account for the typical things like a toxic work environment or an aggressive workload. Readers, I’m curious to know: how do you know when it’s time for a change?