If you're ready to stop settling for a high-paying job that drains you and start building a career that fuels both your purpose and your paycheck, this episode is for you.
Rachel Speckman shares her approach to reverse-engineering your career—starting with what you want and working backwards to make it happen. Through vocational psychology and practical coaching, Rachel helps high achievers find meaningful, well-paid work.
She introduces the concept of "company crushes"—organizations whose values align with yours—and provides actionable tools like the internal resume audit (documenting your favorite moments at each job) and the day-to-day audit (tracking tasks, time spent, and enjoyment percentage).
Rachel also discusses the four pathways for career change: pivoting within a company, applying elsewhere with intentionality, going fractional, or starting your own business. She shares how to create your own personal board of directors for accountability and strategic introductions.
Key Takeaway: "Would you drive a car that was 60% falling apart? If one of the four pillars of life—where you live, who you live with, your health, and your profession—is off, you need to address it."
Kelly Callahan-Poe: If you're ready to stop settling for a high paying job that drains you and start building a career that fuels both your purpose and your paycheck, this episode is for you. Welcome to the Two Marketing Moms podcast. I'm Kelly Callahan-Poe and today's episode is called Reverse Engineering Your Career with Rachel Speckman. Rachel helps high achievers find meaningful, well-paid work aligned with their talents and values through the lens of vocational psychology. Welcome Rachel.
Rachel: Thank you so much for having me.
Kelly: I thought some of the key things that you talk about are really interesting. I love this idea of reverse engineering your career. Tell me what that means.
Rachel: Reverse engineering your career is in some ways exactly what it sounds like and in some ways the devil's in the details. Most people I work with are 30s through 60s—they've had some work experience, they're not right out of school, and they've had a collection of jobs or skills. At some point they start to know, "I'm really good at this thing and I want to do this thing more."
But the job market says "do this and apply for this thing." What I do with people is help them double down on the skills, values, and problems that they want to solve. That's when you're going to be in as much flow state as possible. Then we figure out how to either create that role internally, or realize it won't exist in this place and you need to create it elsewhere, or become fractional and do this in a variety of places.
Kelly: So you call these four pathways, right? Pivoting within a company, applying elsewhere with intentionality, going fractional, or starting your own business?
Rachel: That's right. When you're stuck or you feel as though the magic of Kelly or Rachel is not being utilized, we can coast for a while, but ultimately we want to be using our skills and our time wisely. A lot of people say "I want to have meaning, I want to feel like I'm contributing." I call it the three Cs—contribution, challenge, and community. That comes from meaningful work.
Kelly: You talk about company crushes. Can you tell us what that means?
Rachel: A company crush or professional crush is someone or a company where you're like, "I really like what they're doing. I like how they're marketing themselves. I like what they're aligning themselves with." Something in you is drawn to what they're doing. Just like you would want to get to know a crush a little bit more and explore if there's a "there" there.
I'm working with someone in the fitness industry who's very drawn to what Peloton is doing. Well, what is Peloton doing? It's thinking wildly differently about fitness. So now she's trying to hobnob with a few people at Peloton, starting to get trained there. That's kind of a company crush leading into potentially a long-term relationship.
Kelly: So how do you help your clients find or create their ideal job description?
Rachel: One of the first things is I have clients do what I call an internal resume. Instead of putting your resume out there for LinkedIn, you sit down and say, "What were my favorite moments at that job?" Maybe nobody saw that moment, but you know it was your favorite.
I have a client who said their favorite moment was leaving early after they had done their work—it showed them that they don't want to be beholden to someone else's time clock. So you're putting this together and then we look at it and say, "What are the themes here? What are some of the embedded values that actually emerge through my favorite moments?"
We look at different domains: Were they introverted or extroverted moments? Were you in ideation or execution mode? Then I say, "If you could pick one of those to be in more." Some people say they want 50-50. Okay, let's think about roles that are 50-50.
Kelly: You have a background in vocational psychology. What role does mental health play in choosing a sustainable career path?
Rachel: One of my first questions is: "What percent happy are you overall in your job?" Most people find me when they're 20 to 40% happy at their job. I fundamentally believe there are four pillars to our life: where we live, who we live with, our health, and what we do professionally.
I say, if one of those is off, would you drive a car that was 60% falling apart? Would you live in a house that's 60% falling apart? There's no blame or shame in this. But as proactive as we can be and say "uh-oh, this is heading south" or "this is feeling a little more toxic"—the more we can address it.
Vocational psychology is literally the field of how does our work influence our mental health and how does mental health influence our work.
Kelly: Do you have any other favorite tools or exercises to help people find work that's aligned with what they're meant to do?
Rachel: The internal day-to-day audit. Think about the last three to five days of your professional work. What have you spent 40% of your time doing? Put that in column one. Column two: what percent of my time am I doing that? Column three: what percent do I enjoy doing that?
So let's say one-on-one therapy is 80% of my time, but my enjoyment is only 20%—well, we've got a major disconnect. But what if editing is 5% of your job and you want it to be 80%? Now we're seeing opportunities. Therapy and coaching is dialing up what's going well and dialing down what's not going as well.
Kelly: You also had a really interesting idea about creating your own personal board of directors.
Rachel: Every company has a board of advisors helping with finance, overseeing volunteer engagement, whatever the case. Well, you are basically your own CEO—the captain of your ship. Who are the three to five people that are on Team Kelly, Team Rachel? Not at this job—these are the gems who want to see you succeed no matter where you are.
Then you say, "I'm gonna put together a board of advisors. I want to reach out to you from time to time." They're your eyes and ears out there, holding you accountable. I have a board of advisors that I send a quarterly update to—literally. Most people get their next job through their networks. So the board of advisors is making strategic introductions for you, holding you accountable, having you think differently.
Kelly: These are some great tips to help us all reverse engineer our careers. Thank you for joining us. Please find Rachel's contact information on twomarketingmoms.com or wherever you listen to your podcasts. Don't forget to subscribe and share.
Rachel: Thank you.
