How to Choose the Right Career for You, with Dalan Vanterpool

Listen On:

One of the biggest challenges that you will face in your professional life is choosing a career. It’s not only recent college graduates that face this challenge. Most of us will change careers at least once during our working lives. How do you find the job that’s the best fit for you, no matter your age? Find Your Dream Job guest Dalan Vanterpool says that before you begin thinking about certain roles, you need to ask yourself five specific questions. The answers to these questions can help you land a job that not only allows you to excel in your work, but also provides an atmosphere that you enjoy being a part of every day.

About Our Guest:

Dalan Vanterpool is a private banker and career development expert from the British Virgin Islands. Dalan hosts the Focus The Fire podcast. His show helps young professionals build meaningful careers that lead to more time, money, and freedom.

Resources in This Episode:

  • Dalan’s podcast, Focus the Fire, will show you how to transform from an average employee to an amazing leader.
  • Dalan offers essential career advice for young professionals on his website,
  • If you wait for employers to bring up salary, you’re wasting your time and energy. My guide, How to Talk About Money in an Interview, shows you how to do salary research before meeting with a hiring manager. Learn how to be more comfortable talking about money and get the tools you need to request a higher salary.
  • From our Sponsor: Sneaker School is an online certificate program that lets you explore career paths in the footwear industry and learn from some of the biggest names in the business. Visit to start mapping your career in the sneaker world.


Find Your Dream Job, Episode 181:

How to Choose the Right Career for You, with Dalan Vanterpool

Airdate: March 6, 2019

Mac Prichard:

Today’s episode of Find Your Dream Job is brought to you by Sneaker School. It’s an online certificate program from the Fashion Institute of Technology and Complex Media.

Sneaker School lets you explore career paths in the footwear industry. And students get first-hand advice from some of the biggest names in the business.

To learn more about Sneaker School, visit

Mac Prichard:

This is Find Your Dream Job, the podcast that helps you get hired, have the career you want, and make a difference in life.

I’m your host, Mac Prichard. I’m also the founder of Mac’s List. It’s a job board in the Pacific Northwest that helps professionals find fulfilling careers.

I believe that lifelong learning is the key to a successful career. And to get a better job, you need to learn the job hunting skills that will help you find the role of your dreams.

That’s why we’re here today. Every week on Find Your Dream Job, I interview a different career expert. We discuss the tools and tactics you need to find the work you want.

This week, I’m talking to Dalan Vanterpool about how to choose the right career for you.

Dalan Vanterpool works with young professionals. He says one of the biggest challenges this group faces is picking a career.

But it’s not just a problem for Millenials, according to Dalan. Most of us will change careers one or more times in our 40+ years in the workplace.

Job seekers who make the best choices, Dalan tells me today, ask themselves five questions.

And the answers help these people land in careers that let them excel and look forward to going to the office.

Want to learn more? Listen in now at the Mac’s List studio as I interview Dalan Vanterpool about how to choose the career that’s right for you.

Dalan Vanterpool is a private banker and career development expert from the British Virgin Islands.

Dalan hosts the Focus The Fire podcast. His show helps young professionals build meaningful careers that lead to more time, money, and freedom.

He joins us today from Panama City, Panama.

Dalan, thanks for being on the show.

Dalan Vanterpool:

Mac, thank you so much for having me and glad to be here.

Mac Prichard:

Yeah. I just want to begin by giving a huge shoutout. I know you recently recorded your 100th episode on your show, Focus The Fire. That is a big milestone. Congratulations.

Dalan Vanterpool:

Hey, thank you so much. We were talking before in the pre-show, it’s a huge milestone for us here. We were pushing on that for quite some time to make sure we get out there and cross that 100 mark. It feels good to be in the triple digits.

Mac Prichard:

Well, I encourage listeners to check out your show. I had the good fortune to listen to a number of episodes to get ready for this conversation and you’re doing great work.

Dalan Vanterpool:

I appreciate it. Thank you so much.

Mac Prichard:

You’re welcome, and our topic today is careers and how to choose the right career for you.

Who do you see struggle with this question?

Dalan Vanterpool:

There are a couple of groups, Mac, I see struggling with this. It starts out first with the early career seekers. People who are halfway through college or they just finished college or are trying to choose a major or they just graduated and now are just like, “Whoa. Okay, now I actually have to do something real with my life besides just wake up and go to class.”

There’s that group, but then there’s also the, I call them, the young professional. They’ve been out of school for a little while, maybe they’re one or two years into a career and they’re now realizing that they’re doing something that they don’t absolutely love or the rewards aren’t what they thought it would be; it’s not all it was cracked up to be in their heads.

There’s the group that I usually see struggling when I talk to them about how to choose that right career and what they want to do. It happens as well in older folks but I think that by the time you get older, you’ve already settled into whatever you want to do, even if you don’t love it sometimes. But that younger crowd is who is usually struggling with this question about how to choose the right career.

The “what do I do with my life?” question.

Mac Prichard:

I know that I, too, see older workers, particularly who are in their 50s thinking about changing careers altogether and I know a lot of what we’re going to talk about today will be applicable to them, but in your practice, I know, too, that you work with young professionals in their 20s and 30s.

When you have those conversations, I also know from our earlier conversations and reading your blog, that you encourage people to answer 5 questions when they think about choosing a career and I’d like to walk through those 5 questions.

How’s that sound?

Dalan Vanterpool:

Absolutely great. We can definitely do that.

Mac Prichard:

Alright. Number one on your list is, you ask people to answer this: “What do you believe?” Tell us more about that. Why is that an important question?

Dalan Vanterpool:

I like to start there because I think when folks get bombarded with the question of, “What do I want to do with my life?”, they get super stressed out and they try to get directly into the mechanics of, “What’s the name of the company? What’s the salary?” And all those questions, don’t get me wrong, you know as a career professional as well, those things are important but I try to get them to step back just a little bit and before we start thinking about the different companies you might want to work for, let’s take an internal look at what you actually believe.

What are your limiting beliefs? Because at the end of this process, we want to make sure that you end up choosing a career or working with a company that doesn’t conflict with your personal values, with the things that matter to you. If you’re the kind of person who says, “Well, I love spending lots of time with my family.” Okay, great, maybe you don’t need to be thinking about a job that requires 80 hours a week; and that’s not something to feel bad about, it’s just what you believe in, what’s really important to you.

I try to get people to start thinking internally first before we even go out there and start talking about resumes or anything else that might come as part of the job hunting process.

Another part of that is, also, what kind of things are you definitely not willing to do? For example, I remember in my early career, I was in public accounting and a number of the folks that started with me, especially a number of the female coworkers, they said, “I don’t want to make partner. I like my job. I think it’s great. I enjoy accounting.” But they looked at what partners had to do, especially women partners and said, “Look, I really value spending more time with my family.” Or different things that are more important to them and they said, “I just don’t want to be partner.” And that, as much it might seem like a negative thing or somebody’s copping out, I think that’s an important distinction for folks to make early on. In being very clear and honest about what they believe and what matters to them because that’s going to help you and save you from a lot of heartache and confusion later on.

The first step in this is usually, for me when I’m talking to folks, “What do you believe?”

Mac Prichard:

Okay, and the answers typically are about professional goals; do I want to be partner or not? Or about values that matter personally.

Are there other elements that you like to see people draw out when they answer that question, “What do you believe?”

Dalan Vanterpool:

Yeah, absolutely. We usually get into talking a lot about folks and their limiting beliefs about money in particular, because financial stress, financial struggles are obviously a big thing that comes up in a lot of relationships, personal development things, and your personal life. I ask folks, “Where do you stand on this money question? Do you think that’s important in life? Do you want to have luxury and luxurious things in life?” And the answer varies from person to person.

Some people don’t mind living a minimalist life; they don’t care to travel much, they don’t want to have fancy cars and even things. Other folks feel like they didn’t have that growing up and they want to do things. They want to do big things for their community.

You have to choose at the beginning of this here, when you’re talking about what you believe, do you want to be the person making a donation or do you want to be the person that has so much money that you’re starting a foundation or creating a charity that then goes out and makes bigger donations? Either one is fine but I think there’s just an important point for us to sift out here as we’re thinking about what career you want to go into.

Mac Prichard:

I know the second of your 5 questions is, what’s the problem you want to solve? And why do job seekers need to think about problem-solving when they choose a career? Why is that important?

Dalan Vanterpool:

Well, my philosophy in this is, money changes hands when problems get solved and if you’re going into a career, the only way you’re going to be able to sustain that performance at a high level, the only way you’re going to be able to put out that quality even when the money isn’t there or even when it gets tough or when you have to work on a weekend or stay late or something, it has to be something that is deeply meaningful to you.

I say, think about that problem you want to solve. What is that thing out there, and this is the easy way to help narrow down if you’re juggling a lot of options, if you have listeners who are listening to this show and are juggling different options, what is the problem you actually want to solve?

What is it that you go around and you say, “Oh man, I wish someone would just figure out how to do that.” Or, “I think I know a way to do this particular thing better.” Or, “It really bothers me when people do this particular thing here and it’s not done well.” If you start thinking about the problem that you want to solve, all of a sudden now, you’re carving off leaves or carving off layers from this thing and you’re getting closer and closer to the actual career that you want to choose.

Choose or identify a problem where, 1) you have a deep passion for getting the solution to that problem and something where you think you can be excited to pour loads of energy into it because if you go into a career, especially if you’re planning to be successful. If you’re listening to the Find Your Dream Job podcast, I’m already assuming that you’re a high performer or you’re well on your way to being there and you want to do well. Well, to get to the top of the food chain in any career, whatever you try to do is going to take a lot of time and energy, so you want to make sure if you’re going to be spending 40+ hours, (I don’t even know why we say 40 hours a week anymore because everybody works more than 40 hours) but if you’re going to be spending that much time doing any particular thing, you want to make sure that it is something that you really care about. Something that you really want to solve.

I say, focus on finding a problem that you personally, not just the company out there or in a broad way; no, find something that you want to dedicate 10, 15, 20 years of your life to solving.

Mac Prichard:

Can you share an example of someone you’ve worked with who looked at that question and they came up with an answer? What was the problem they decided to solve?

Dalan Vanterpool:

Yeah, sure, absolutely. A friend of mine, she was looking at…she came to me and we were talking about careers and different things and she said…I asked her the question, “What is the problem that you want to solve?” A problem, at that point, she was looking at a number of different things, a number of different options on the table, and said, “Look, I really want to help people become more confident in themselves.”

I said, “Okay, we’re getting closer. Well, what kinds of people? What is the actual thing you want to do?” She was like, “The problem is I want to help people get confident so they can do x,y,z.”

As we started digging deeper and deeper into really shaving off the generic layers off of that answer, it really got down to the point where she said, “Look, I want to help this kind of person, solve this problem. I want to help them become more confident so that they can then go on to teaching people how to do a particular thing.”

See, here she was able to say some things that really jumped out to me. She said, “I want to teach.” I said, “Ah, okay, so you’re not on the side of just creating random things; you don’t want to sell products, you actually want to teach.” Then we can say, “Okay, based on that problem you already want to solve, you just talked about it, we’ve now identified the kind of person, or you’ve hinted toward the kind of person, and we’ve hinted toward the way you may want to deliver that solution.” That’s how that starts shifting in there as you start to think about what problem you want to solve.

You’re able to sustain it for a longer period of time and do more work because it’s not just a job anymore, it’s something that you’re actually personally invested in.

Mac Prichard:

Your third question, as you take people through this process is, to get clear about the clients that a company works with and you recommend people ask, who do I want to serve? How does this help get clear about a career choice?

Dalan Vanterpool:

Sure, and this came up for me especially when I was thinking about starting a podcast and I got in contact with a gentleman named John Lee Dumas from Entrepreneur on Fire and in the process of getting ready and preparing for this podcast, one of the things that John makes you do, you have to create what he calls an avatar.

Now, the avatar is literally answering this question, who do you want to serve? The interesting thing about this is not just a general answer like, “I want to serve young people.” No, if you were to think about the avatar, you’re actually trying to create a literal person. My avatar for the podcast actually has a name, Angie. She has an age, I know how many kids Angie has, I know what struggles Angie’s going through. You’re literally thinking deeply about the person that you want to serve.

That, again, is going to inform the kinds of careers that you might want to choose. If you’re more interested in working one on one with people, if you’re thinking more of older people, younger people, men, women, whatever the specific groups are, that’s going to help you niche down and narrow down even more on what you want to do. Then you can identify companies or businesses that serve those particular groups, or that particular person.

This is all, again, just helping you to narrow down the wide swath of things that you could possibly be doing with your life. If you scroll down LinkedIn or you pull up Indeed or whatever it is and see all these jobs, is it helping you to sift through for yourself which ones actually matter to you?

Mac Prichard:

Okay, there are two more questions. We’re going to get to them after the break but just to repeat the first three that listeners should consider answering, what do you believe? What problem do you want to solve? And, who do I want to serve?

Stay with us. We’re going to be back in just a moment and we’re going to talk about the other two questions you need to answer when choosing the right career for you.

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Again, that’s

Now let’s get back to the show!

We’re back in the Mac’s List studio. I’m talking with Dalan Vanterpool. He’s the host of the career podcast, Focus the Fire.

He joins us today from Panama City, Panama.

We’re talking about how to choose the right career for you and Dalan has a model. It involves answering 5 questions and just before the break, we talked about question number 3, getting clear about who I want to serve. I love that because often, again with all of these questions, we’re going to talk about the final 2 in a moment, you’re thinking about what you want to do, why, and who’s going to benefit and what I’m not hearing you say, Dalan, is you can choose a career by going to a job board and looking at job listings.

Dalan Vanterpool:

Now, that’s an option. People do it all the time. I think that’s why people like Mac are out here trying to help us do that in a more effective way or better way.

Yeah, you can jump out to a job board and lick your thumb and spit in the wind and spin the wheel and stop on something, but I think that is what has actually contributed to a lot of what we see here and now in the workplace. A lot of folks who are, you know, you’re good at doing things, you can do your job, you’re capable, I should say, of doing it, but it’s not something you’re deeply passionate about. It’s not something that brings meaning to your life.

I can tell you right now, I’ve been on jobs where it means something and jobs where it doesn’t. I’ve been in jobs where you work 50, 60, 70 hours a week and if you’re going to put that much time into something, time away from your family, time away from other things that matter to you, you want to approach this in a more structured way than just picking things on a job board.

Which is why I recommend these kinds of questions to sit down in a quiet space and do them. Whether you do them in a day or you do it over the course of a week or it’s something that you revisit more than once as you’re going through that job hunting process. Or even if you’re not job hunting, it might be a good exercise to do right now wherever you are on your current job.

Mac Prichard:


Dalan Vanterpool:

Look at what you’re doing now and see if you can answer these questions and then do you like the answer that are coming up based on the job that you’re doing right now?

Mac Prichard:


Well, let’s get back to the 5 questions. Number 4 is, once you are clear about who you want to serve and those problems you want to solve, number 4 is, how do you deliver that solution?

Tell us more about that. What do you want to get at with answers to that question?

Dalan Vanterpool:

Sure, by the time you get to this point in the exercise you probably have a few ideas about, maybe the companies that you want to work for or the kinds of things you want to do, the kind of business you want to start if you’re trying to be an entrepreneur or freelancer. But now we’re getting down to some more tactile parts of this process. How do you want to deliver that solution?

Are you the kind of person that’s thinking about creating a product? Are you trying to be an inventor kind of side? Are you interested in product or are you thinking more about a service? Just like the example I gave before, the person I was talking to, they were more interested in the service side. They wanted to teach.

You can start thinking as well, how do you want to put this out there? In distribution channels? At this point, they start sounding almost like you’re not thinking about a job, you’re actually thinking about a business and I think that’s absolutely the conclusion that you need to get to at some point in your job search and stop thinking about yourself as, “Oh, I’m an employee and I’m trying to find a job.” No, you are a service provider or you have a product.

What you’re trying to find is a client out there that’s willing to pay you for it. Even if you’re not going to be an entrepreneur, I try to encourage people to really start thinking along these lines, you are a provider. You have a business. You are a business.

People who say, “How was work today? Do you like your boss?” I was like, “I don’t have a boss. I have a client. That’s the person that pays me, and I’m trying to make my client happy today by doing what they’re paying me to do.” That’s a really empowering mental shift for people to make because then it takes you out of this subdued role in the job hunt. You’re not just out there hoping that someone blesses you with a job and you’re there taking pressure or taking your instructions from someone else, no, you’re actually out there serving clients.

Think about it, if it was a regular business, you’re providing a service and your client pays you, so same thing in the office or whatever job you go to do, you’re actually trying to find the ideal client. Think about how you want to deliver that solution. If it’s say, if it’s a one on one kind of thing you want to do, you want to work directly with people in that consulting way. Do you want to do something where you’re able to reach a lot of people all at once? If that’s the case, maybe you need to be thinking about a business that’s already established rather than trying to go out there one on one knocking on doors.

As you start to think about this medium for how you want to deliver that solution, it again helps you narrow out and cross out some of the possible options that are out there for your career choice.

Mac Prichard:

I like your point about the importance of the “how”, because once you’re clear about what is you offer and you think about your employer as a client, it’s very empowering, isn’t it, Dalan?

Because you realize, if the relationship you have with your existing employer isn’t working for you, if you know what you have to offer and the value that it provides, it makes it easier to make a transition, doesn’t it?

Dalan Vanterpool:

Absolutely, and it also makes it easier when you’re thinking about doing any kind of career transition moves because now you’re not just thinking about finding another job, you’re thinking of it from the point of view where you have skills, you’ve been working on those skills, whether it’s schooling, whether it’s through practice, seminars, whatever it is, podcasts that you’re listening to, you’ve been honing those skills and increasing your value and you can walk into the office, I think, with a sense of empowerment, that sense of value. This is not arrogance, mind you. It’s not arrogance to say, “I can get up and leave this job whenever I want to.” No, because this is your client

You wouldn’t want to just abandon a client unexpectedly, but when you start thinking about career transition things, you’re not necessarily job hunting, you’re client hunting. Where can I take my skills? Where can I shop my skills around to find another client that might get value from what I have to offer?

Mac Prichard:

What’s your best tip for listeners to figure out what it is they have to offer? Because self-assessment can be hard and people struggle with being clear about the skills that they provide and the value of it.

How do you see people do this well and figure that out?

Dalan Vanterpool:

One of the best things I ever heard along these lines came from a gentleman named Michael Burt. He has the podcast, I think it’s called Coach Burt, and he said, this was about a year and a half ago, he said, “A lot of times, our self-assessment is greater than our market value.”

I remember listening to this podcast and when he said that I almost dropped my phone, pulled out the headphones, about to toss them across the room. He said, “Your self-assessment can often be higher than your market value.” Now, while that’s true, I think there are also cases where it’s the other way around. Your self-assessment, you might be being a little bit too hard on yourself.

I tell folks, look. Look at the things, again, look at the questions that we talked about before, look at the things you enjoy doing, fine, but look at the things that you really do well, and a good hint at this is to ask yourself, and I know that means more questions here, but ask yourself, “What are the things that people consistently come to me for guidance on?”

What are the things that people see you as an expert on? When a question comes up in the office, when a question comes up in a project, where do people lean on you? What skill sets do people lean on you for? That can be a really good hint as to what your value is, what is the source of your value, and how good it is.

Mac Prichard:

Well, let’s talk about your 5th question, and you suggest that people ask themselves, how do I want to live? Why is this important?

Dalan Vanterpool:

This last one for me is extremely crucial and I put this one last for a reason because I think sometimes when we get into these self-assessments, these questions, these introspective exercises, we forget that no one is actually looking at this stuff besides us. We think we have to sound very noble and altruistic, and we have to sound a particular way to impress people and…no, let’s have an honest conversation with yourself.

How do you actually want to live? What does your quality of life look like?

I’ll tell you a quick story. When I was getting ready to go to college, I went through high school and I was the kind of kid, I won’t say I was rebellious. My parents might say differently, but once I didn’t feel like something mattered, if you couldn’t convince me that something was important, I just didn’t pay attention to it. Coming through high school, I wasn’t good at sports and music was my thing. I decided I wasn’t going to be athletic and I wasn’t going to be “hot and cute guy.” I was going to be the talented guy.

I went hard with music and I wanted nothing more when I graduated high school than to either go to law school, because I loved watching Perry Mason and Matlock, or I was going to go to music school, and my dad, my parents sat me down and they said…you know, they had this kind of question with me, this conversation. They said, “How do you want to live? What are the things that are important to you? Describe to us the quality of life that you think you would want to enjoy.”

I’m negotiating with my parents at this point, so I try to be very verbose and articulate about things and I listed off the things that matter and my dad said to me, “Well, son, I’m listening to what you say you want to do in life and how you want to live and I got to tell you that, while nothing is wrong with being a musician, it takes a long time for a musician to get to that kind of lifestyle, if they ever make it at all. You’re going to have to go through a lot of years if you ever do make it to be able to live that kind of lifestyle.”

After having that kind of conversation and being realistic about it he said, “Look, do you want to be the musician that ends up not having a lot of money but knows a little bit about business or do you want to be an excellent business person who also happens to be a good musician.” And that’s where it kind of went down. He said, “Look, do something. Choose a career that’s going to be able to afford you the lifestyle that you actually want.

“You’re not setting aside all the other things that you’re interested in, there’ll be time for those things, although to a lesser degree, but do something that really allows you to live the way you want to live.”

For example, for me, I want to be to a place where if something happens to my family, whatever happens, and all the income burden has to fall on me, I want to know that I’m doing something that makes enough money that I can support that. That’s a big deal for me.

That’s part of how I want to live. I want to travel. A big joke I make all the time, or not a joke, a big claim I make a lot on the podcast is that I want to live a lifestyle where I don’t always travel in first class, but I want to have the option to travel in first class. I want to be in coach but I want to be there because I don’t feel like paying the extra amount. Not because I’m not able to pay the extra amount.

I encourage people to have these kinds of conversations with themselves and to really be honest about how they want to live so that they can create that meaningful career and choose a career that can get them down that path.

Mac Prichard:

Well, terrific advice, and it’s been a great conversation. Tell us more about what’s next for you.

Dalan Vanterpool:

Sure, Mac. Next up, this year we’ve got a lot of exciting things coming up. The biggest thing for me this year is I start doing more coaching calls. In 2018, we were doing a lot of these informally here and there but we’re really going to start structuring that, especially by the time this goes live.

If you want to have a one on one coaching call with me, to talk through your career challenges, we can do that, as well as, we’re getting ready to set up some free webinars. Folks can access all of that over at They will be able to access our blog, YouTube channel, and the Focus the Fire podcast. They can do all that over there at

And connect with me on social media at dalanv.

Mac Prichard:

Great. Dalan, thanks for being on the show today.

Dalan Vanterpool:

Thanks so much for having me.

Mac Prichard:

I love the 5 questions that Dalan posed about how to choose the right career for you. One question that stood out to me was asking yourself, “How do I want to live?”

When you ask that question, it not only helps you get clearer about the work you want to do but also about the finances that you’re going to need to support the life you want.

That’s important because when there’s a job offer on the table, you’ve got to be ready to talk about money. So many people aren’t prepared to do that.

We’ve got a guide that can help. It’s called How to Talk About Money in an Interview.

You can get your free copy today. Go to

Get the salary you need. Go to

Well, thank you for listening to this episode of Find Your Dream Job.

Please join us next Wednesday when our guest expert will be Colby Reade. He’ll share his informational interview tips for young professionals.

Until next time, thanks for letting us help you find your dream job.