Why So Many Career Transitions Fail, and How to Avoid the #1 Mistake Professionals Make, with Rachel Spekman | #574

Agi Keramidas

Why so many career transitions fail and how to avoid the number one mistake professionals make when transitioning. Welcome to Personal Development Mastery, the podcast helping midlife professionals in transition turn uncertainty into clear direction and confident next steps. I am your host, Agi Keramidas.

Join us every Monday for in-depth conversations with experts and every Thursday for shorter solo episodes with insights and tools you can use. This is episode 574. If you are looking to move beyond surface level career success and reconnect your work with meaning, this conversation explores how fear, ego and incremental change shape the path to fulfillment.

Before we start, if you are a midlife professional ready for change, I offer one-to-one coaching to help you get clear on what's next and create a realistic plan forward. As a former dentist who has made this transition myself, I know how challenging this can feel. To explore this, visit personaldevelopmentmasterypodcast.com slash mentor. That's personaldevelopmentmasterypodcast.com slash mentor. The link is in the episode description. Now, let's begin.

My guest today is Rachel Speckman. Rachel, you blend business insight with emotional intelligence and you are passionate about helping successful professionals find the courage to live unfulfilling careers and create work that's both purposeful and profitable. Rachel, welcome to the show.

It's a pleasure to have you with me today.

Rachel Spekman

Thank you so much for having me.

Agi Keramidas

Today, we will explore career success and turning that into fulfillment, which they don't necessarily go together. Before we go there, what I would like to start with, I mentioned in the introduction that you've worked in marketing, startups, therapy. These are three very different domains or worlds, if you want.

How has that combination of those three shaped your understanding of what drives career fulfillment?

Rachel Spekman

Great question. I love to follow my curiosity. When I started in marketing, I was curious about how a company successfully talks about itself, makes money.

I was doing an MBA at the time. How a company actually operates. Then I was curious about, well, how would a small company do this?

When I was in marketing, I was working with very large brands, Microsoft, Lenovo, Dunkin' Donuts, these multi-conglomerate companies. Then I thought, well, how would somebody with very few resources do this? I followed that curiosity.

Then my life took a turn. I'm happy to talk more about that. I realized that when I would sit down with the startups, at a certain point, I would say, how are you?

They would talk about how they were and I'm stressed about this. Then they'd say, well, here's what's going on with my company. I would pause and I would say, wait, I'm actually more curious about how you're doing than how your company is doing.

I share this because the thread is actually following what interests you most, and then building a career around that, which I call reverse engineering your career. It sounds easy, probably, and it's not. It sounds maybe like a quick fix.

It's not. It's really that combination, as you said in the intro, of knowing what intrigues you, what problems you want to solve, and what you're naturally good at that the world will actually pay you to do.

Agi Keramidas

I want to start or to continue, actually, since we are going to talk about transition or change in career. You mentioned the reverse engineering. We'll talk about that a bit later, but I would like to ask first, why, in your opinion, in your experience, do so many high achieving professionals, successful people, remain in careers that they know it makes them, I will use a strong word, makes them miserable even.

Why do they do it and remain that even though they know they are unhappy? Let's start with this fundamental question.

Rachel Spekman

The shortest and longest answer is fear. It's fear of many things, fear of change, fear of the unknown, fear of financial, I'm not going to say, maybe volatility or that changing. It's this shackled feeling to, well, this is my bed.

I got this law degree. I got this engineering degree. Now I have to do it.

Sometimes you do have to do it for a little bit. You have to pay back your student loans. You have to, I help people, what I say, make a calculated risk plan.

I don't encourage anyone to quit or to be impulsive without a plan, without a network, without a strategy, and potentially the right certifications to make a change. But really I think people stay stuck because they feel fearful of change. They have real bills, responsibilities, just like I do, just like you do.

And I think the other thing is people feel like they have to do it all at once. So I love to share that I ask everybody in my intake form, what percent happy are you? Or maybe to your question, what percent miserable are you?

But I try to be asset based. So I say, what percent happy are you? And do you want to guess out of a hundred what most people say?

60. That would be nice. Most people find me when they're 20 to 40 percent.

Oh, wow. Okay.

Agi Keramidas

So my choice of word miserable, it was not far from the reality.

Rachel Spekman

No, it's very appropriate. And it really starts to take a toll on your mental health, your physical health, your relationships. And so most people find me or reach out to me, and I'm not shaming them.

That's just literally the data. Because when we're when we're really starting to feel stuck, that is when we realize this is unsustainable to be this stuck. I will ask someone as a joke, would you stay?

Would you drive a car that was 80 percent falling apart? Or would you live in a house that was 60 percent falling apart? And of course we say no, but we stay there for our careers.

And I work with people and say the goal is to get to 80 percent. This answers your question about why they stay. It's not we're not going to go from 20 to 80 percent overnight.

I say it takes about four to six months of getting of hard work to get unstuck. And you're going to go from 20 percent to 25 percent to 30 percent. And so it's an incremental change and it's not an instant gratification all at once change.

Agi Keramidas

I think that goes without saying. And anyone that believes that doing that instantly will create the life of their dreams, they're probably going to see that this is not exactly like that. There is a journey, a path to that.

Is it OK if I add a quick metaphor to that?

Rachel Spekman

I'm a very visual person and I come from education. So I love the metaphor or the visual of a duck swimming on the water, which is that you think it's gliding and it looks beautiful, but underneath it's paddling really fast. It's going through muck, it's stuck in the weeds.

We see what looks like the top, but we have to work on what's underneath as well.

Agi Keramidas

So I will stay for a bit to let's say there is someone listening now and they are at that stage. They have started to or they are realizing that this is unsustainable, use that word, that they are not happy with how their life is because they are in a career that does not fulfill them anymore. Perhaps it did in the past, but anymore.

So they are contemplating the options. What I would like to ask you is, is there a question that you would like to give to someone listening that is like that, that they can sit with it perhaps tonight, just ponder on it to perhaps help them towards a direction, a decision?

Rachel Spekman

Yes, I have a few, let's call it preliminary, almost thought starter exercises, but I encourage you to grab a pen and paper or an Excel to do these. So the first one I love to give people is I will say, design your perfect work day. What time are you waking up?

Are you by yourself? Are you with a community? What projects have you worked on?

What problems are you solving? Really walk through eight to nine. I have a cup of coffee and we're talking about this situation, nine to 11.

The more detailed we can get about what our perfect day looks like, we can start to understand what's actually close to it right now and what's far from it. What lines up around how we're spending our time and how that's a reflection of what our values actually are and what skills we're using. Another exercise I like to give people is, this is sort of a similar way of doing that, but it's a little bit different, which is I will say, look at the last week of your life, work life for the last 48 hours.

And I want you in an Excel to write down the top five things that you spent your time on. So let's just say it's podcasting, emailing, setting up meetings, Excel, whatever it is. In the next column, I want you to write what percent of your time you were doing that throughout your workday.

And then next to that, what percent enjoyment you have of that task. So you can start to see, I spend 80% of my time doing Excel and I enjoy it 5%. Okay.

There's a major disconnect there. Or conversely, I spend 10% of my time editing copy for the website. And I love it.

I feel so alive when I'm doing that. I want to spend more time doing that. That is a, let's call it quote basic or in therapy, we say meet the client where they're at.

Yes. We can dream about where we want to go. Let's identify where we are right now.

And even having that data, Oh, I have an extra hour in my workday. I mean, that would be nice, but let me do that thing. That's a little green that I love doing.

So the more we start to, I say, turn up the volume, this is what I say therapy is and coaching at the end of the day, it is turning up the volume on the things that are going well and turning down the volume on things that aren't going as well.

Agi Keramidas

The way you describe this, for me, I understand that it applies more to someone who wants to make, let's say a pivot in what they're doing. If let's say someone wants to do something completely or has the feeling that what they're doing now, there is nothing here on the second column that has much enjoyment, you know, and they want to go to a different direction, but they're not sure what direction that might be. Perhaps they have an idea, but as you know, in these cases, there is a lot of uncertainty that can cloud once, you know, clear decision-making process.

So for someone who still exploring, you said describe your ideal day. So let's say someone says, Rachel, I have no idea how I would like my ideal day, working day to be, because I'm not sure what kind of work I would like to do. What's something you would tell her?

Rachel Spekman

This is what I would say. I would kind of give part two of this exercise, part three. There's a book that I referenced with clients, it's called Meaningful Work.

And it's a great book. And one of the exercises, they call it the three Cs. There are three Cs that essentially combined together to create our work feeling meaningful.

And those three Cs are community, contribution, and challenge. And so I would ask that person, what's your favorite community that you've been in to date and why? What's your dream networking room?

And it could be, there's no judgment. That's a huge thing I work on with people. We're not judging ourselves.

Oh, I was trained to be a doctor, but I really want to be in a room full of restaurant owners. Great. Well, now you know.

Yeah. What is the contribution or the impact that you want to be making? Do you want to be working with individuals?

Do you want to be working with policy? What does contribution mean to you? And then what's the last challenge that you solved that you felt really great about?

And history has a way of kind of repeating itself. You don't need me to tell you that. One of the favorite exercises that I do with people early on is called the internal resume.

So I want you or whoever's listening to take out your resume and for each job, nobody's going to see this except for you. And maybe a coach, and maybe chat GBT, if you use chat GBT, but I want you to write down your favorite moments at that job. Maybe nobody saw what you were doing.

Maybe you went in early. Maybe you did a remote job that you didn't even think you could do. You met lead a team.

What were some of your favorite moments and what was actually happening in those moments internally for you? It's so different than the external resume that we put out there, but that's a really good way to start to get unstuck to start to say, Oh yeah, I did. I just had somebody do this.

She was like in high school. I love that. I got to run this huge event.

Great. What did you love about it? Oh, I got to bring these people together.

All of a sudden it's this aha goes off about the things that you love to do. You could call it the flow state, but it's really just moments that you're proud of.

Agi Keramidas

That's great. You mentioned, and I will go to that because it is, I believe quite important to discuss today. You use the word challenge.

So let's move on now the timeline and let's discuss about someone who has gone past that initial stage of being at the crossroads and they have taken the plans and they are already in transition. Tell us about the biggest challenge that one faces during that time.

Rachel Spekman

I mean, the answer is it varies so much, but I will say, I think a constant challenge that I experienced when I made a large career change and that I see my clients experience is let's call it reputational management. So I left a fairly cushy job. I wasn't that motivated at all.

It was fine, but I just, it was not the right room for me. That's the other thing. I call it the right room.

What rooms do you want to be in? I was not in the right room and I went to become a therapist from working with investment bankers and corporate, all kinds of things. And really one of the largest challenges was having the courage and being brave and saying, I'm doing this.

And I had all kinds of people say, are you okay advising me against it? This is not a great move for you. I didn't ask them.

They were just telling me their own stuff. And I will say, I'll put my therapist hat on for a moment. When we talk about big things, grief, transitions, even buying a house, large investments, people will tell you their opinions when you don't ask for it.

And so one of the, there's one thing to want to make a change, because I identify it as three stages. I say mindset, transformation, and accountability. The accountability, because really the hardest part is actually making the change itself, because you are going to get a And so I think I'm going to reference what one of my dear bosses said to me when I was about to have my first child.

He said, can I give you some advice? I said, sure. He said, my advice is to be very careful about whose advice you take.

And I would say excitement, pure self knowledge. I work with people to create a, I call it a five-year financial plan. I mean, really having that kind of know-how, doing a lot of pre-work before you make the change, that is such a great, right?

I mean, if you think about success is the best revenge, we're not trying to be revengeful, but the more confident you are, the more you can, let's say, armor yourself for people's unsolicited advice.

Agi Keramidas

Tell me about one more challenge then apart from the fear of the reputation that you said.

Rachel Spekman

Yeah. The second challenge is the ego. The ego goes on a journey here.

And when you go from a subject matter expert, even if you hate the job, people come to you, you have a reputation, you have a degree in it, to let's call it beginner's mindset. It is very humbling. And I will say the older we all get, the more we think we should quote, no.

And as I said, I have two small children and I just model. I don't know. I don't know the answer to that as much as I can because it actually creates an environment where I'm still a learner all of the time.

And so I would say really, you know, I'm giving my own examples. I have a client right now who's making, let's call it, I help, I call it a small, medium, large change. She's making a medium change to sort of within her industry, but a new focus.

And we had a call two days yesterday and she said, I am so scared that I'm not going to know the answer in the room. Everybody looks at me for the answers in the room. And we did some prep around great.

So you're going to be the curious person. You're going to be the confident learner. And so really some of our earliest fundamental experiences around what we knew in school, what we didn't know, where we placed in our class.

I mean, all of these things actually come up and it's really important to be kind to ourselves. And one last thing I'll say about this is I asked that client, I said, on day one of the job where you are now the expert, were you the expert day one? No, you were not.

So sometimes you got to start again.

Agi Keramidas

Thank you for this answer. You used the word humbling experience, which I think it is very appropriate to use. And I think many can relate to that.

I can relate as my, with my own professional transition, that it does take some time for you to get. I remember, I will tell you about myself when I did our practice dentistry. I didn't just start practicing dentistry.

I had to go to university for many years. And then the beginning, I was very, very, you know, unsure about my capabilities built as I was practicing. And I think it's important what you said for someone to realize that reaching a level of, you know, competence and authority in their careers and then having to start in a way, certainly at a much, you use the word beginner, I think beginners mindset.

What I want to ask about this actually is transferable skills of that. What, what, what's your thoughts now on someone that has done the transition? How many or which one of those skills could they use to position themselves in a, at least psychologically, not necessarily in a matter of knowledge, but at least there's confidence to be reinforced because they have had all of those skills, which may not necessarily be the same skills that they need in what they're doing now, but to some extent they can be transferred.

I hope my question makes sense.

Rachel Spekman

I think it does. And if it's okay with you, I'll use you as an example of transferable. That's fine.

The student is the teacher. The teacher is the student. You were a dentist, right?

And I know very little. I was a teacher. There's a technical aspect to the mouth and the teeth and the gums.

And there's also the human experience of making someone feel confident, making somebody feel less nervous, managing the systems that you had to other people. Same thing for me in teaching a different technicality. So often, and this, this actually, I think is a reflection of the job descriptions.

This is why I help people write their ideal job description before they go and apply. I say, let's, let's create your own bullet list of your ideal job and what skills you are using. And that's also reverse engineering it, but your transferable skills, there is a technical skill that you would have to learn if you were to become a pilot, let's say, but the transferable skills of people, communications, relationship building, that is, that is not industry specific.

And it's sort of my personal belief that the more technology and AI and everything, and there's a lot of fear around that in the job market, the more we're actually going to need to develop and hone in and explain these transferable skills as it relates to human to human connection.

Agi Keramidas

Definitely. And that's why I was asking. And since you brought me as an example, you said the, being a dentist requires attention to detail.

I mean, otherwise you, you really want to be a good dentist if you're not careful about the tiniest details. So this is certainly being thorough and meticulous and paying attention to the details. It is a transferable skill or making others feel at ease.

And so that's also, you know, an invitation from me to someone listening to think about the skills that are transferable, because it is, they are much more than one realizes perhaps at a blink. So is there, do you have an exercise for that?

Rachel Spekman

I have a one page Word doc that I use. It's actually from the Wall Street Journal. I really like it.

And it's, you could, I mean, you could obviously Google or look up top skills, but this actually summarizes, let's call it the 20 most transferable skills. I'm happy to have that as a, as a document that people can access. And it really is helpful.

Even when you look at that client that like that high school event, okay, you were organizing people. You had the attention to detail. You had vision.

You have, there's a lot in there. And I think the more we, we, I'm not living your life and you're not living my life. The more we live our own lives.

We're like, oh yeah, of course I just did that event. Wait a sec. Let's slow down.

You did a lot to become a dentist. You did a lot to run that event. And so it's, it's actually, what's, what then has to happen is, is the personal marketing side, which is communicating these skills and feeling really confident about them.

Agi Keramidas

Which is probably a topic for another conversation. It was not such a huge thing. Absolutely.

Rachel Spekman

I mean, I do want to tell you one of the top, top experiences I have as a coach, literally my mission is I help high performing professionals. I will have people who come to me, they run multi-billion, million dollar budgets and they manage teams and they say, do you think I'm high performing? So, so we have that on the table as well.

Agi Keramidas

It's a good, good example. And it is important to realise that in our,let's say self-doubt that what you described or imposter syndrome We are not alone It is something that You know, it's part of being humans or human I suppose

Rachel Spekman

This experience can be very isolating to feel stuck in your career And of course, we all have to be professional and put it on so I I want just real quickly I noticed I was having a conversation with you as a client and then the next client and I thought these clients need to hear from each other because that's Invaluable in life to have somebody who's in the same moment that you're in I know this as a when I was a brand new parent when you're caring for aging parents You just need support somebody who gets it at that moment so I've transitioned to now doing group coaching and having clients connect with each other and it's it's a whole another world when you Bring in community to this

Agi Keramidas

Definitely Rachel As I'm going to start wrapping this fascinating conversation up Shortly, the first thing I wanted to ask is where do you want to direct the listeners?

Rachel Spekman

To find out more about you and your work So you can go to made for more coach Dot-com. That's the name of my company made for more coach Have a training there You can set up a consult with me and I'd love to talk to you there That's great.

Agi Keramidas

And I also have two quick questions. I always ask my guests and The first one is what does personal development mean to you?

Rachel Spekman

There's a theory and in therapy and social work called both and and the idea is that I'm both Enough and I'm always working to to be a better sense of myself And that's my that's my definition of personal development both and And hypothetically if you could go back in time and meet The 18 year old Rachel, what's one piece of advice you would give her? Well, first I would give her a big hug and say it's gonna be okay Yesterday too, but I mean I would say no I would really say You got this and and I think especially for me when I was 18 I felt like I had to have every single thing figured out and I it's taken me What like 20 years basically to realize? Oh my gosh, that's such a myth.

Agi Keramidas

And that's such a myth Rachel, I want to thank you very much for this wonderful and useful. I'm sure your conversation That we had and to wish you all the very best with your career and life I would like to to hear your parting words and in particular Your message to someone who has listened to us talking for now the last half an hour.

Rachel Spekman

What is a Parting message you would like to leave them with My intention on getting on the podcast is is yes to share what I'm doing And hopefully I can connect with you and this resonates it. It is truly if you leave this feeling a bit more empowered if you have one more idea of Something you could do a friend you could reach out to who's doing something interesting then I Feel that that is success and I won't see the success. Maybe I will maybe you'll let me know But really my intention is for you listeners to understand That it's so cheesy with the name of my company I laugh every time I say it, but I always say it came from a client who was in a really toxic work environment My name my company name was just called Rachel Spekman coaching and then I said to the client Emphatically I said you're made for more than this toxic company and the client said that's the name of your company made for more and I was like, oh my gosh, you are right. And again, that's we didn't really talk about organically letting things grow but that organically happened and So I would say to everyone who's listening you are made for more have a plan Get it get a group around you of smart people that believe in you

Agi Keramidas

Thank you for listening to this conversation with Rachel Spekman I hope it has given you a fresh perspective on how to approach career transitions with clarity self-compassion and a practical plan rather than impulsive leaps If you are a midlife professional in a long-standing career ready for a change I offer one-to-one coaching to help you get clear on what's next and create a realistic plan forward As a former dentist who has made this transition myself. I know how challenging this can feel to explore this visit personaldevelopmentmasterypodcast.com slash mentors That's personaldevelopmentmasterypodcast.com slash mentors The link is in the episode description Until next time stand out don't fit in