GOAL DIGGER

Get Unstuck in Your Career with Your Next Move, Best Move

Jenna Kutcher 

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August 23, 2021

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When you look at your career path, do you see a series of happy accidents that led you to a role you love? Has your career advancement been intentional and strategic? Do you feel ready for your next career move, but not sure how to seek it out or strategize a career leap that brings you to your best next step?

I know this show is mainly about entrepreneurship and advice for business owners, but part of that is an incredible community of side-hustlers, starting and growing a business in your off hours and dedicating your days to advancing your career. Is that you? Then you’re going to love this conversation with Kimberly Cummings.

Kimberly is a career expert and leadership consultant, and her advice helps people navigate next steps in their careers, foster strong relationships to support those career moves, and create a plan to achieve career aspirations. Ready to make your next career move, your best move? 

Where Her Story Begins

“So it began stumbling and I think that’s pretty normal for most folks,” Kimberly began. Like so many of us, Kimberly had dreams of what her life and career would look like after college, but the reality was that she needed a job with a paycheck, whether she loved it or not. Her first job had a paycheck, of course, but it was nothing like she envisioned. 

Her next career move decision was based on making more money, but she didn’t love that job either. She explained, “The first strategic career decision I ever made was when I decided I wanted to go some place where I was going to be happy.”

That move led her back to higher education and the world of career services, helping other people connect to jobs. It was a pivotal moment for her, “I still remember the first student who had a job as a direct result of working with me. And I was like, this is it. I love this.”

She threw herself into professional development, learning everything she could to ascend to the director level within her department. Kimberly ended up leaving the field after 10 years and pursuing a career in diversity, equity, and inclusion in the corporate area, but for that decade she threw herself into career development to make sure she was the best in her field so she could pursue her next move.

Getting Unstuck

Do you feel stuck or stagnant in your career? Kimberly walked through the first step of getting unstuck. “The first thing that I have everyone do is really take stock of where they’ve been in their career and figure out what is it that brings you joy? What are you passionate about? What are your skills? 

“And then in those skills, what are the things that you want to continue to do for the rest of your career? And even more importantly, what are the things that you never want to do again?” Kimberly continued. “Because I think sometimes we can build careers based upon just things that we’re good at. But even though we’re good at something, it doesn’t mean that we enjoy it, and that’s where sometimes we can feel ourselves getting stuck.”

It’s like starting a business in many ways. When you’re a first time solopreneur, you’ll do everything necessary to get your business going and growing, but everytime you figure out what’s better served for someone else to do for you. Kimberly explained, “I think professionals don’t necessarily think about their careers the way entrepreneurs do, in that you can work and build a career that is built upon your strengths and your passions, and that’s what kind of keeps you from getting stuck in this rut of just unhappy.”

Relationships and Career Growth

Kimberly says in her book, “it’s important for you to create a career that creates opportunities for you. And that’s one of the things I drive home. All of my clients who work with me, you have to create a career that ultimately brings things to you.” Part of that is building strong relationships in your career. You never want to be a cold applicant sitting in a pile of resumes — it’s about forming strong connections and relationships so when you go to apply, people are already familiar with your work.

Kimberly stresses that, “Relationships are one of the only things that can expedite your success.” She recognizes that this can get uncomfortable for some people, that they want to be hired based on their own merits and work ethic alone, not through a relationship. 

But think of it this way, Kimberly said, “You essentially need to use relationships in the way business owners use social media. If you are doing work by yourself and nobody knows about it, there’s no marketing, no nothing. It’s really hard to attract clients. In the professional sense, when you are out there doing great work in your role, and you want to move and advance, other people need to be able to co-sign and that’s what relationships can do for you.”

Kimberly shared her favorite ways of making these kinds of connections and relationships in the digital world. Press play for her actionable advice. 

More from Kimberly Cummings

What happens when you become a boss and you’re responsible for developing and supporting the career of other people? Should you be developing a 5-year, 10-year, or other something-year plan for your career? How can you pivot into the career direction with intention and actually land the job you want? We cover all this and more — hit play wherever you get your podcasts for this conversation with Kimberly Cummings.

Follow Kimberly on Instagram @kimbcummings and pick up her new book ‘Next Move, Best Move’ at your favorite local bookstore. 


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A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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