Episode 65: Reverse-Engineering Your Career
High-performing professionals don’t have to choose between high pay and purpose. This episode explores how to reverse-engineer your career and job search to find work that aligns with your values, strengths, and income goals.
Blog Recap
Feeling stuck in a high-paying job that drains you? You’re not alone. Career coach and therapist Rachel Speckman helps high-achievers find meaningful work that aligns with their values—without sacrificing their paycheck.
The Four Pathways Forward
When you’re ready to make a change, Speckman identifies four strategic options:
- Pivot internally – Create or pitch your ideal role within your current company
- Apply elsewhere with intentionality – Target specific roles at new organizations
- Go fractional – Work across multiple companies without being tied to one employer
- Start your own business – Build something from scratch
Two Powerful Exercises to Get Unstuck
The Internal Resume Audit
Instead of listing what looks good on paper, write down your favorite moments at work—even the ones nobody else noticed. Look for patterns: Were you in ideation or execution mode? Working independently or with others? These themes reveal what truly lights you up.
The Day-to-Day Audit
Create three columns: What you’re doing, what percentage of your time it takes, and how much you enjoy it. Most people discover a major disconnect—spending 80% of their time on tasks they only 20% enjoy. The goal? Get to 80% enjoyment by dialing up what works and dialing down what doesn’t.
Company Crushes and Your Personal Board
Pay attention to organizations that intrigue you. What draws you to them? How they market themselves? Their values? Their innovation? Use that “crush energy” to explore potential opportunities.
Meanwhile, assemble your own board of advisors—three to five people who want to see you succeed regardless of where you work. Send them quarterly updates and a clear, forwardable introduction about what you do. Most jobs come through networks, so make it easy for people to help you.
The Bottom Line
Ask yourself: What percent happy are you in your day-to-day work? If it’s below 60%, something needs to change. You wouldn’t drive a car that’s 60% broken—why accept a career that is?
The path to meaningful, well-paid work isn’t about making one giant leap. It’s about increasing your happiness by 1% at a time, reverse-engineering your career from what you actually want rather than what’s available.
Episode Transcript
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 Speckman
Thank you so much for having me.
Kelly
We were just chatting saying that it seemed like it was so long ago that we talked, but at the same time, I do recall the conversation very readily. 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 like many things the devils in the details. So, if we think about most people I work with are 30s through 60s let’s call it. So, they’ve had some work experience they’re not right out of school and they’ve had a collection of jobs, or they’ve worked at one place and a collection of skills and 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 is do this and do this and apply for this thing. And so, what I do with people is I help people instead of being scatterbrained as someone my clients used, I say, let’s really double down on the skills, values and problems that you want to solve. Because that’s when you’re going to be in as much flow state as possible. And then how do we either help you create that role for yourself internally where you are, which does mean pitching it at times, and I can get more specifics and get into more specifics and give examples. How do we say it’s actually not going to exist in this place and I’m going to have to go either create that for myself at a new firm or 80 % of that role. It might not be 100 % or I’m actually going to start my own thing. I helped somebody yesterday.
I could talk more about that with this great clarity call, which is one of the things I offer people. Or I’m going to become fractional. I’m going to do this in a variety of places. And I don’t want to be beholden to one employer.
Kelly
Got it. So, you call these four pathways, right? Pivoting within a company, applying elsewhere with intentionality, going fractional or starting your own business, right?
Rachel
Yes.
That’s right, that’s right, because when you’re stuck or you feel as though the special sauce or the magic of Kelly or Rachel is not being utilized, and we can coast for a while, but ultimately, we want to be using our skills. We want to be using our time wisely and we spend so much of our day in life, for better or for worse, you know, at work or feeling connected to our identity and not everybody, some people.
I’m married to somebody who can kind of go to work, feel fine about it, and come home, and that’s fine. A lot of people say, I want to have meaning, I want to feel like I’m contributing, I call it the three Cs, I want to feel that there’s good growth, or it’s a good heart, I sometimes call it, around contribution, challenge, and community. That comes from meaningful work. I can’t say I originated that. I always like to give source, to the sources that exist.
And we could talk, if we get into it, I reverse engineered my career search to find myself where I am. that’s how I even fell into what I’m doing or chose to do what I’m doing.
Kelly
So, you talk a little bit about company crushes. Can you tell us what that means?
Rachel
Mm-hmm. Okay, so it’s a company crush or a professional crush. Someone or a company where you’re like, really like what they’re doing. I really like how they’re marketing themselves. I really like how they’re talking about themselves. I like what they’re aligning themselves with. So, something in you, consciously, subconsciously, is drawn to what they’re doing, how they’re putting it together.
And you want to get to know them or just like you would want to get to know a crush a little bit more and explore if there’s a there. And so, I do encourage people to think about who are the companies that you think, wow, like I’m working with somebody in the fitness industry. And so, she’s very drawn to what Peloton is doing. Okay, well, what is Peloton doing? it’s kind of thinking wildly differently about fitness it’s kind of blowing up like it started with the bike and then it’s expanding and all kinds of things. So now she’s trying to hobnob with a few people at Peloton, starting to get trained there, right? So that’s kind of a company crush is leading into potentially your crush can become a long-term relationship. It doesn’t always have to, but you’re exploring the crush energy.
Kelly
So how do you help your clients find their ideal or create their ideal job description?
Rachel
Okay, so there’s a few different ways. So, and I like to be as practical as I can on podcasts, so that everybody who’s listening, whether we work together or I have the privilege of working with you or not, but just that you walk away saying, I could do something to get a little, even if you’re thriving, we can still get even more unstuck, right? Or we can still be more thriving. So, I want to give some practical tools. So, one of the first things is I have clients do what I call an internal resume.
So instead of putting your resume out there that you’re going put on LinkedIn and all the things, you sit down and say, what were my favorite moments at that job?
Rachel
Maybe nobody saw that moment, but you know it was your favorite. Actually, I have a client who said their favorite moment was leaving early after they had done their work, and it showed them that they don’t want to be beholden to somebody else’s time clock. Right? But nobody else saw that, but they knew that they were finished. So why did they have to stay until 5? OK, so you’re putting this together, and it should just be very natural. There’s just no, you know, then.
Kelly
Yeah, absolutely.
Rachel
Then we start to, we can either put it in ChatGPT, or we can look at it together and say, what are the themes here? What are some of the embedded values that actually emerge through my favorite moments in my career? And we can look in a few different domains. Were they introverted or extroverted moments? Were you in ideation or execution mode? Were you…
in again, sort of that entrepreneurial or operations mode. So really start to think about some of these dualities, like where were you? And then I do like to say, if you could pick one of those to be in more. So, introvert, extrovert, if you could pick one to be in. Some people say, I don’t want to, I want to be 50-50. Okay, let’s think about roles that are 50-50.
Or let’s think about roles that are more forward-facing. I’m working with someone who’s at an insurance job right now and she’s really in the analytics end of it, like all day long. And she’s really missing humans. And so, we’re now trying to figure out what are data analyst human-facing jobs.
Right, so this is the way that we start to even just like turn our attention towards what’s lighting me up with that sense of clarity, intentionality, which is a very trendy word, so I’m going to use that word. And I think it’s trendy for a reason. And then, so that’s kind of like sole option number one. I will say practical option, especially if you’re applying for jobs right now.
Look at the last five jobs you apply for and pull out the bullets, just sort of brand-new word doc of the bullets or the tasks that you are most excited about and put it in priority order. And while you’re doing it, say in a typical day or a typical week, I’d like to spend 40 % of my time on this, 20 % of my time on this and 10 % of my time on this. then all of a sudden, you’re creating your dream position as opposed to, I’ll take a little bit of this and a little bit of that. That’s how most of us apply to jobs, right? Or we just see, yeah, I’ve been the assistant title this person, so I’m going to do it again. Which parts were your favorite? So, there’s something that’s like very basic about it, but also kind of radical because it’s different than how we normally apply to things.
Kelly
You use vocational psychology in your coaching practice?
Rachel
I do not have a formal background in it yet, I am, so I am a social worker, so I changed careers. So, I started out as a teacher. I was a teacher for seven years. I loved running projects. I loved being in front of the classroom, but I did not like the classroom discipline piece of it. I pivoted and used those skills. I helped people with what I call small, medium, or large pivot. So, I made a medium pivot.
Kelly
Okay.
Rachel
I took those skills and started working in after school and nonprofit organizations to run a lot of their projects, operations, and budgets, sort of like a classroom, but at a larger scale. Then I really got into doing that. I started doing an MBA part-time and realized, well, my favorite part of what I’m doing is actually getting systems up and running. So, I started working with startups and I was doing that for about seven years.
It was an infusion of a lot of my skills, and I loved it. And then life happened, life happens, and a lot of people find me at a transition. So, I ended up having a long journey to have my two kiddos.
And when I did have my first child, I went back to work and I basically was like, this feels emptier than it used to.
And that’s what I call the asymmetry of work. Like it looks like you’re doing all these things, right? And you are doing these things, but how are you actually feeling about it? And so, I was like giving these keynotes and I was leading all kinds of really cool workshops, and it was fine. I knew how to do it, but I didn’t, I was literally crying in the bathroom. I felt very disconnected from my work.
Kelly
Yeah.
Rachel
and I took a really long hard look at myself and…and I started working with a coach and then it was the pandemic and at that point things had been bubbling for a long time. So, through my family planning journey, I had worked with a therapist, and I had sat down with my therapist, and I said, I really like what you’re doing. You seem to be connecting with people; you’re running your own shop. She was a teacher as well at a university. said, those are all the things that I like to do.
So, I made a very large pivot. I call it my largest adult calculated risk. And I left being a senior director in the corporate world to become an intern in social work school and I made a five-year financial plan for myself and said in five years I need to basically be back to what I’m doing financially. And I can’t even tell you; it’s like I, I’ve, I don’t want to say I’ve arrived, but I’ve reversed, like I’m doing what I love doing. I love, I said, want to, I want to connect with people and get paid for it. And I know it’s a funny thing to say, we have to figure out what we love to do and how do we get paid for it. And so now I’m a fully licensed therapist. I have my own private practice. I just left the agency I was with for three years where I did a lot of my training.
And I have an office downtown and then I telehealth. And then the coaching business kind of started almost accidentally because I had worked with a lot of people along that path. And people said, especially when I made the change to social work school, I mean, I was working with like investors and angel, you know, all, and they were like, are you OK? What’s going on? You know, and I said, well, I’m actually I actually been working on this for like a long time behind the scenes. That’s the thing. You never know who are working on behind the scenes.
Or I say with their pillow at night, you know, whatever. mean it’s Side hustle. Yeah. Yeah, and that’s the other thing I did a lot of things to experiment if I would like to be a therapist I ran a fertility support group I got involved with a volunteer organization. So, there are a lot of ways talk about company crushes I had a crush on an organization, and I said I’m not trained to do this. Could I do this, and they said yeah, we’ll help you know, of course
Kelly
I call it a side hustle.
Rachel
All the volunteer organizations are looking for support. But that’s a really nice way to actually just like almost like trying on a coat like does this fit me? Would I want to do this more of my time? Okay, well if the answer is yes, then we have to figure out how you get paid for it.
So that was kind of a longer story of my journey. yeah, and I come from a pretty, like, two parents working the same job for 30 years, not entrepreneurial, right, in that way. And I’m four months into fully working for myself.
Kelly
So, to build on that in terms of your focus on vocational psychology and pairing that with mental health, what role does that really play in choosing a sustainable career path?
Rachel
Yeah. So, one of my first questions that I ask everybody, and I encourage all the listeners to think about, what percent happy are you in your day to day?
Kelly
Wow. Is that a question?
Right now, I’m tremendously happy, but you know, that changes day to day, right? It changes the job that you are. But I made this happen of where I am today, you know?
Rachel
It does.
There we go. So, most people find me, unfortunately, when they’re like 20 to 40 % happy at their job. And I do really fundamentally, and this is like psychology kind of 101, but like there are four, I think there are four fundamental pillars to our life, which is, you and I are talking, but I’m talking about like our, this is a one-off. I’m talking about our day-to-day life, which is where we live. our home, who we live with, our family, or whatever that means to us, pets, et cetera, our health, and what we do professionally. Just mathematically, that just takes up most of our time. And so, I say if one of those is off, so people come to me 20 to 40%, I’m to get to your vocational psychology question. say, would you drive a car that was 60 % falling apart?
Would you live in a house?
Right, your health, et cetera. And there’s no blame in this, there’s no shame. I do couples counseling as well. Couples find me when they wish they had found me three months ago, right? That kind of thing. So as proactive as we can be and say, uh-oh, this is heading south, or uh-oh, this is feeling a little more toxic. So, the vocational psychology, the mental health piece is really being aware of how’s my physical health responding to the job.
Do I feel psychologically safe to take a risk here and be myself? And professionally inappropriate and those kinds of things. Do I feel supported with where I want my career to go?
And the more we can answer these things, and again, it’s not a binary yes or no, but in general, do I feel as though I’m able to expand here, I suppose.
Then we can start to understand, vocational psychology is literally the field of how our work influences our mental health and how does mental health influence our work.
A lot of the field of vocational psychology is how does long-term unemployment impact our mental health? And also, just the job market in general. There’s a webinar today that I actually can’t attend, but it’s just managing all the buzz that we hear about the job market right now, everything that’s going on. It’s a hard time. It’s a very hard time. And also, when there’s hard times, there’s opportunities to say, well, what actually does the market need right now. And I would say it really needs a lot of authenticity. A lot of people living in their, like you’re saying that you’re very happy right now because you’re like, I’m going to figure out, I’m going to tap into my own strengths.
Kelly
It is out of that life stage too, right? You make different decisions when you’re 25 and you don’t have any dependents versus 55 and you’ve got kids and aging parents.
Rachel
Absolutely, and I feel very lucky because I just left Brandeis University where I was in college counseling for the last three years. And so, teaching a class there right now called Career Clarity and Mental Health.
And it’s been, well, I always, I really have a lot of faith in the next generation because people who are 22, I mean, they can do some of these exercises. They don’t have the dependence, but I challenge everyone in the group. do a lot of coaching around getting into your, there’s your comfort zone, your panic zone. How do we get more into your stretch zone? Anyway, but I challenge everyone to make a new connection to rewrite their resume based on their strengths and skills and their, I mean, happens to be the people taking the class, but they’re really game for it.
Kelly
That’s good and that’s nice and that’s hopeful. So, for the next generation and for my own children, you shared one tool that you think is important, which is like the resume audit. Do you have any other favorite tools or exercises that you can share with us to help people find and thrive their work that’s really aligned with what they’re meant to do?
Rachel
Mm-hmm. Yeah. So, here’s another tool that I think is, again, I like to kind of use tools that are free and just easy to use on your own. So, it’s called the internal day-to-day audit. Okay, so let’s, I’ll do it with you if that’s okay. So, it’s basically, if you think about the last three to five days of your professional work, what have you spent?
40 % of your time doing it. You don’t have to answer; you can be fictitious about it. But for me, I’ve done one-on-one therapy with people, for example. Okay, then I say, so that’s in column one, one-on-one therapy. Then I say in the next column, well, what percent of my time am I doing that? 80 % of my time.
Column three is what percent do I enjoy doing that?
So, let’s say it’s 20%. OK, well, we got a major disconnect between the two.
But what if what I’m doing is, you know, I love editing. This comes up with a lot of people who are blogging or something, and that’s 5 % of their job. But they want to be doing it 80%. Okay, well now we’re seeing where these opportunities are. Because at the end of the day, I really do think therapy and coaching, is dialing up what’s going well and dialing down what’s not going as well. How we do that, the tools, the person, the team, I those are the details.
But that’s what it is. So, this is a tool to just look at the last, just look at your day to day. What are you actually spending your time on? And for most people it’s like emails, right? Or moving a project forward. And then you can say, well, is this a contribution? Is this community? Is this a challenge that’s aligned with me? But I really do recommend that internal audit, which sounds similar. It sounds like the internal resume audit, but it’s actually your internal day to day audit. Just take out an Excel, Google Doc, and three columns. So, column one, the project, column two, what percent time it is, and column three, your percent enjoyment. And then you can say, well, what’s something I could do to turn it up a little bit more, even just 1 %? Or turn it down a little bit more. So that’s a tool I like to use with people, because I say my goal is to help people get to 80 % enjoyment.
Kelly
It’s fair.
Rachel
That’s funny, most people are like, that sounds impossible. you know, especially if you’re at 20%, you’re like, I said, we’re not going to get, we’re going to, we’re not going to go to 80 % tomorrow. We’re going to be 20 % today and 21 % tomorrow and then 22%. And that’s why I say for most people, takes about six months to figure out how to get unstuck.
Kelly
I believe that to be true. You also had a really interesting idea about creating your own personal board of directors. What did you mean by that?
Rachel
Well, yeah, it’s just like that. OK, so every company, most companies, nonprofits, for-profits have a board of advisors. They have somebody who’s helping with finance. They have somebody who’s helping with overseeing volunteer engagement, whatever the case is. So go back to when your company crushes. Go back to any company and see who’s on the board of advisors.
Well, if you think about yourself, how do you, whether you work for somebody else or you work for yourself, you are basically your own CEO. That’s really my theory. Depends on how much you take. You’re the CEO of your own life. I mean, it sounds a little cheesy, but it’s true. The captain of your ship, all of those things. Who are the three to five people that are on Team Kelly, Team Rachel?
Not Team Rachel at this job. These are the gems who want to see you succeed no matter where you are. And hopefully at this point in your career you’ve collected a few of them.
And then you say, okay, I’m going to put together, it can be very informal, a board of advisors. I winna reach out to you from time to time, here’s my job search, let them help you. So, another tool is definitely having a third-party introduction or third person, excuse me, introduction ready. So, I send this to everybody which is like.
Rachel is a therapist and a coach, and she can help you with this. Please forward this along to anybody. So, then you’re just like spreading it. So, Kelly is a marketer who does X, Y, and Z. People want to help, but they need to know what to help with. And so, the board of advisors, they’re basically just like your eyes and ears out there. And they’re also holding you accountable. So, I have a board of advisors that I send a quarterly update to.
Literally. I asked for this. I have four people on it. Three people who are like, I don’t have time but send me the email. know, sometimes I get a response. Sometimes I don’t, but it’s really…
It does require a level of motivation, but it returns itself so much over because I know people, I can’t do it alone. Even if you work for yourself, I mean, I can’t do it alone. And most people don’t shoot the messenger here, get their next job through their networks. So, the board of advisors is making strategic introductions for you, is holding you accountable, is having you think differently.
Kelly
They’re there for.
Rachel
So, everybody can, you know, so anyway, that’s sort of one of the Board of Advisors exercises that I give people. And there’s a lot of gratitude because people are paying it forward to help you, hopefully, and then you’ll pay it forward for somebody else.
Kelly
These are some great three to five tips that we can all use to reverse engineer your career. Thank you for joining us. Please find Rachel’s contact information on twomarketingmoms.com And don’t forget to subscribe and share. Thanks for joining.
Rachel
Thank you.
Contact Information
https://www.facebook.com/RachelSpekmanCareerConsulting/about
