Episodes

  • You’re Always in the Job Market: How to Manage Your Career Before You Need To, with Kelly Kay

    You’re Always in the Job Market: How to Manage Your Career Before You Need To, with Kelly Kay
    Oct 19 2026
    A lot of people spend plenty of time thinking about how to succeed in their jobs, but far less time thinking about how to choose the right jobs in the first place.
    In this episode of Career Sessions, J.R. Lowry sits down with Kelly O. Kay, managing partner at executive search firm Heidrick & Struggles and co-author of Show Up to Win: The Insider’s Guide to Getting the Career You Want.
    Drawing on decades of experience advising executives and companies, Kelly shares an insider’s perspective on how to manage your career more deliberately. He explains why you should take the recruiter call even when you’re happy where you are, how to test your value in the market, what makes a candidate’s story compelling, and how to evaluate whether an opportunity is actually right for you.
    J.R. and Kelly also discuss why internal candidates sometimes struggle against outsiders, how to recover professionally after being fired, the subtle ways candidates sabotage themselves during the hiring process, and why your reputation can follow you for decades.
    Whether you’re actively considering a move or perfectly happy in your current role, the message is simple: the best time to manage your career is before you need to.
    Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/kelly-kay/.
    For more career guidance and resources, subscribe to my member community at https://community/pathwise.io
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    37 mins
  • Stop Following Someone Else’s Career Playbook, with Andy Paul

    Stop Following Someone Else’s Career Playbook, with Andy Paul
    Oct 12 2026
    You may not think of yourself as a salesperson, but every day at work, you’re selling something—an idea, a proposal, your capabilities, or even yourself. In this episode of Career Sessions, J.R. Lowry sits down with sales expert, author, and longtime podcast host Andy Paul to explore what the rest of us can learn from great salespeople about influence, curiosity, and human connection. Andy explains why the best way to persuade someone isn’t to push harder, but to understand what matters to them. He shares how asking better questions and truly listening can strengthen relationships, why curiosity is often trained out of us as we move through school and work, and how to avoid making conversations about ourselves. The conversation also moves beyond sales to a bigger career question: Are you building the career you actually want—or simply following someone else’s playbook? Andy discusses why success is situational, how to find environments where you can be yourself, the importance of choosing the right boss, and why it’s sometimes better to leave a bad fit rather than keep trying to make it work. Along the way, Andy shares lessons from nearly five decades in business—and a reminder that there’s no age limit on taking on new challenges. In this episode, you’ll learn:
    • Why everyone is selling, whether they realize it or not
    • How curiosity can make you more influential
    • The difference between listening to understand and listening to respond
    • Why great questions create stronger relationships
    • How to find work environments that fit your strengths and values
    • Why you should define success on your own terms

    Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/andy-paul/.
    For more career guidance and resources, subscribe to my member community at https://community/pathwise.io
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    28 mins