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How To Explore Careers Without Guesswork, With Gabe DeSanti & Alex Dworsky

In this episode of Career Sessions, Career Lessons, JR Lowry sits down with Gabriel DeSanti and Alex Dworsky, co-founders of Staj, a platform built around a simple but powerful idea: What if you could experience a career before committing to it? They explore why traditional career decision-making is often based on limited information and how that leads many people to feel misaligned years into their careers. Drawing on Gabe’s experience trying nearly 200 different jobs and Alex’s background in corporate America, they discuss how career exploration can shift from guesswork to intentional experimentation.

They cover:

  • Why most people choose careers without truly understanding them
  • How short-term “career experiments” can provide clarity
  • Practical ways to explore new industries without prior experience
  • Why curiosity and initiative matter more than a perfect resume
  • How to build credibility quickly when pivoting careers
  • The role of networking and real-world exposure in unlocking opportunities

They also share insights from building Staj and what they’re learning about how people test and transition into new paths.

If you’re early in your career or considering a pivot, this conversation is for you.

Follow Career Sessions for weekly insightful episodes just like this.

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/gabe-desanti-alex-dworsky/

Listen to the podcast here

 

How To Explore Careers Without Guesswork, With Gabe DeSanti & Alex Dworsky

Broken Traditional Career Decision-Making Process

Choosing a career is one of the biggest decisions we make and yet it’s one that a lot of us make with surprisingly little information. Think about it. We had down a path based on advice from friends or family. Maybe a class or an internship but mainly, it’s a lot of guesswork. We rarely get to see what a job looks like day-to-day before we choose that path. This is a big reason why a lot of us end up wondering as we get into a job, whether we’ve chosen the right direction for ourselves.

Our guests are trying to change that. Gabe DeSanti and Alex Dworsky are the co-founders of Staj. A platform built around a simple powerful idea. What if you could experience a career before committing to? Gabe has been on a mission to build the world’s longest resume. Trying out shops across a wide range of industries to better understand what different careers can involve. This journey of experimentation became a big part of the inspiration behind Staj.

Alex has spent her career inside Corporate America seeing first-hand how careers are built and how people often end up disconnected from the work they’re doing. Along the way, she noticed that many of them were trying to make this life defining career decisions without real exposure to the jobs, industries and people behind them.

In our conversation, we’re going to be talking about why traditional career exploration is often broken, how people can run small career experiments to figure out what they want to do, and how someone can break into competitive industries without traditional credentials. More importantly, we’re going to focus on practical advice. Things you can do to explore new paths, make better career decisions, and build a career that fits who you are. Whether you’re just starting out or well into your professional journey. I’m J.R. Lowry and this is Career Session.

Gabe and Alex, welcome. Thanks for joining me on the show.

Thank you for having us.

Thanks for having us.

Let’s get right into it. You started Staj because you felt like the traditional approach to choosing a career is broken. What’s wrong with the way we’re doing it?

Careers Chosen Without Self-Understanding Or Clarity

A lot of people choose their careers when they have no idea what they want to do in their lives. They either listen to their college career people or their parents or whatever they think is right for them. When you’re 22, you don’t know what you want out of life, what you want to do and what you’re good at. It doesn’t give you an opportunity to try it before you commit to something. The job market or a career placement doesn’t align with how people are working.

A lot of people choose their careers when they have no idea what they want to do with their lives. Share on X

Do you think this is an element of being linked to Gen Z and what they want out of work? Is there still a COVID hangover that we’ve all felt psychologically has been continuing to his generation of people entering the workforce? Is this something that’s gone back for than that?

It’s gone back further. I’m not Gen Z. I’ve seen it when my generation arrives at the time that they’ve been working for 10 to 15 years. It’s not aligned with their passions or what they want out of life. I’ve seen it with anybody who have been in a job for a little bit too long. It’s not giving them the passion that they want back. It gets people excited to realize that there’s more out there than what they’re doing. Maybe they can do it and make money and be successful.

It does go back farther than just our generation as well. We’re seeing it more now because of the internet and our access to so much. People are able to connect on the fact that maybe we are aligned in the careers that we’re supposed to be in. It’s more of open discussion topic now more than ever.

There’s probably a lot of truth to that. I’m Gen X and on the old side of Gen X. When my generation was starting in the workforce, we had no clue what we wanted to do either. We stuck with it more. Maybe this generation is willing to do and that’s maybe worth the shift has happened. Do you think the companies have a role in this, too? What are they doing that’s contributing to this lack of alignment in terms of what they’re offering and what people are looking for?

Lack Of Real Job Exposure Before Committing To Careers

When you’re in an interview, you don’t get any sense of what the job is like. Even if you were to talk to one or two people that might be on your team. It’s trial by fire. You’re lucky if it aligns with what you want to do, but I don’t know if want to join a company. You experience it while you’re in the seat. It might be a little bit too late if that doesn’t align with what you want to do. When you’re interviewing, you’re interviewing with a couple people. You don’t get a good sense of the culture or the people that you might be working with. There has to be a better way to know what you’re getting yourself into before you start.

It’s always hard to know up front what a job was going to be, even if you have done something some more to it before you may not have worked in that similar culture. It’s hard to convey all that in an interview process.

Career Sessions, Career Lessons | Gabe DeSanti & Alex Dworsky | Careers Without Guesswork

Careers Without Guesswork: It’s always hard to know upfront what a job will be like. Even if you’ve done something similar before, you may not have worked in that same culture.

 

Gabe, that brings us to you. You’re on a mission to create the world’s longest recipe. From what I can see on LinkedIn, you’re succeeding pretty well so far. You’ve tried a whole bunch of jobs across a very broad range. What motivated you to start experimenting with careers in this way?

It’s a bit of a journey experience in my bones and at my core. I’m a content creator. I love to make videos. Before I was a content creator, earlier in my life, I went to trade school. In trade school, you have to try all the different trades before you pick the one that you’re going to get certified in or the one that you’re going to study for the four years that you’re there.

Going back to that time in my life, I was so curious. I genuinely enjoyed trying all at a country even if it wasn’t the one that I ended up pursuing. I remember being at that time in my life and being like, “I wish I could try everyone’s job.” Even though there’s 8 or 10 years between my time in trade school and when I started this series of trying all different jobs. That thought came back to me eventually. It was something that always stuck with me. That was a big part of how I got started.

What jobs have you done that have completely changed how you maybe thought about that profession?

Career Experimentation Through Job Shadowing And “Stages”

I’ve gone to work with such a wide range of jobs now for almost 200. Every room that I walk into, I walk into it with like my curiosity just open. I’m going in and I’m taking away something from every situation. Some jobs that stand out to me are the more untraditional ones, where people created almost a role for themselves

An example of that is a dog excursion role. There’s not a job title for this. It’s essentially this guy who takes this group of dogs from New York City and brings them hiking every single day for five days a week in Upstate New York. He then brings him back to the city and drops them all off at their houses. It’s like an extreme dog walker as an example of that. It’s not a role that you think of when you think of maybe even being in the pet industry or working with animals. It was a role that he liked created for himself out of a need that he identified.

He started as a traditional dog walker and over time he was like, “These dogs need more exercise. I wonder if I could bring them on a hike.” He started bringing one dog on a hike and then two dogs. Now he brings twenty dogs on a hike at the same time. Alternatively, there’s another woman. Her name is Cindy. She makes guitars out of old New York City building wood. She’s not just taking a guitar template, putting it on a CNC machine and building it.

She’s finding and sourcing this old building wood and then she’s making guitars fully custom and fully by hand from that. That’s for artistry. These people who just dreamed up this thing and put it into action. That’s incredible. I see that in more traditional ways as well of people who are doing one career and then they completely switched up their career. Even though it still might be a traditional pass, but the creativity is what it all comes back to of what people can dream up for themselves. That’s the best part of what I take away from it.

For somebody who’s thinking about doing one of these internships, you’ve done 200 of them. Which is just an astonishing picture, by the way. What can they go into these things doing so that they get as much out of the experience as possible and get his best the sense that they can?

Learning From Real-World Career Experiments And What People Don’t Like

It helps if you have a genuine interest or even just an inclination of interest in an industry. Our hope is when you walk into a new internship or into Staj or into a job shadowing experience, you don’t have to fall in love with it. There’s so much value in identifying afterwards. I didn’t like that at all. Being open to whatever’s going to happen during that day or during that time, you’re going to get the best results. Whether it’s positive or negative being, “I don’t like this.”

To your point, if you go in into one of these conversations with an open mind and build that into the view of, what do I like to do and what do I not like to do? It certainly will help. I would imagine there’s other things you have to be thinking about. Probably there are some awkward conversations. Especially with somebody’s people doing these one-off things like, how much money do you make doing this? For a lot of people, the money part is an important part of the equation.

It absolutely is. That’s what we hope people can learn. Even in my content, I open the videos with this very vulnerable question of, “How much do you make in a year?” It gets people in to watch the video but it’s also that educational component. It’s like, “You can make $200,000 bringing dogs on a hike? You can make $15,000 making guitars?” It is important for people to learn that information and to put that information out there so people know what’s possible.

Understanding Career Values Beyond Just Job Titles Or Money

Also, it’s not just the money but, do I get to work with people? Do I get to be creative? Can I be outside all day? It’s understanding what your values are and see how that aligns to this potential job opportunity.

It’s about understanding your values and seeing how they align with a potential job opportunity. Share on X

How do you make sure, Gabe, when you’re having these conversations that you’re not getting people at one end of the spectrum? One of the things with the influencer market in particular is everybody thinks they can make tons of money. The reality is that, the vast majority of people will never make much money at all doing that. There’s that extreme hockey stick phenomenon. When you’re doing all your interviews, how do you sense check whether this person is an extreme case?

I feel like I hold the whole process very close to my heart. When I reach out to somebody or when I find the person who I’m going to go to work with, even though there’s not like a formal pre-interview. The interview starts from the minute I send that message and maybe get a message back. How long does it take for them to respond? What is their sentiment when they respond? Are they excited? I can gauge what their personality is.

I’m typically trying to find people who are making content about their job. That’s how I find a lot of the people that I end up filming with. Most of the time, they’re just simply making videos because they either are hoping to maybe make that a new part of their business or they want to educate the market on what it’s like working in their industry. I find that those people are typically great people to interview for my videos. It also gives me a sense of their personality.

Alex, how did the two of you come together? What led to the creation of Staj?

My brother is a chef. Before you get a job at a fine dining restaurant, you work in the kitchen for a day. It helps you see if you’re good fit for the kitchen. If the chef likes you, they test your skills. It’s part of the interview process. That’s called Stajing. It’s a French word that means internship. It is such a fascinating concept for me. It inline so well with the fact that you don’t know what you’re getting yourself into before you take a job. Me being in Corporate America, we don’t have that type of experience.

While I was in the midst of Corporate America and seeing people start their own companies, it made me excited to get a better understanding of what other people are doing and how they got started. It helped me take a dive into entrepreneurship. I was trying to figure entrepreneurship while speaking to other entrepreneurs and understanding what this is like and what I have to do. As you probably know, J.R, it’s not just an idea. You have to learn finances, marketing, operations, QuickBooks and accounting.

While I was trying to figure out the marketing aspect of it, I realize that’s not a strength of mine. I came across Gabe’s profile on Instagram. Everything he’s doing by building the world’s longest resume and trying other jobs and showing people what it’s like to work in other industries aligned so well with Staj. I reached out. We shared a couple messages and we met in person. It was so perfect because we aligned on so many things. It was exactly what he wanted to build as a next step to his brand and content. We’re like ying and yang with each other. He’s content and marketing. I am finance and Ops. We come together and have this perfect union while we’re building this thing together.

How does your business model work? Describe it on both sides. Both for the hosts who are offering these stajes and the people who are looking to try something out.

We call it a job shadowing marketplace. We have stajes where the people who want to shadow and host to the people that will be shout out. The business model works where the staj will pay a four-hour experience and that’s in person. We give a commission back to the host to incentivize them for their time and to keep working with us. What’s great about that is that both sides can get what they want out of the experience.

As a next iteration, if the host is looking to hire, if this stock experience is part of an interview process, for example, then we take a recruiting fee if they get hired for a full time job. That’s the today iteration. We’re in our building year because we’re still trying to figure out are use cases in our demographic. We’re offering stajes for free for 2026 to collect a lot of use cases and customer stories. We are planning on taking it to universities, to corporations to figure out where the gap of the market is, what type of demographics see value in this and how to create a recurring revenue model.

What are you hearing so far from the people who have done one of these staj assignments about what they’ve learned both good and bad about whatever job they wanted to try out?

I love the bad part, too. That’s what’s helpful. It’s to see the not-so-nice part about it. A lot of the stajes that we’ve done almost scratched an itch that they were trying to figure out how to scratch. Our stajes were ones that are working in Corporate America, full-time jobs for the last 10 to 15 years. They’re like, “I’ve always wanted to be a private chef or I always wanted to understand what it’s like to work in floral design.”

They’re able to do it. It’s not so glamorous as they think it’s going to be. It’s a lot of hard work but with the ones that they got their hands dirty was such an interesting view for them. The floral design satj was like, “I liked it as a hobby. It’s not something I want to do full-time.” As the private chef, for example. He has worked over and over again with that chef as his help, as his staj. It’s so cool to see. While he’s still keeping his full-time job, he’s slowly entering into the cooking world and getting more experiences. Eventually, he’s going to take the leap. It helps people get that jumping off pad or a little bit more research on like, “Is this something I want to do?” It’s a hobby or this is something where I want to quit my full-time job and do it.

So far, do you have any sense of what the percentage of people who have that yes-no reaction after they’ve had this experimentation?

Since it’s such a new concept, it’s people who are trying out their hobbies where they want to see if it’s possible to do a full-time. A lot of what we have to do is teach the world on, “This is something that’s part of your career exploration process.” If we’re able to get into universities and college space, it’s going to be a lot more informative for students because they have to pick a career path. They have to start after college somewhere.

Where the people were working with now are the Millennials, the 30-year-old, 40-year-old, and 50-year-old to our little bit more risk adverse because they have a mortgage or a family that they have to pay for. Where once we’re able to delve into the university market, we’re going to get a lot more yes-no or interesting facts that come up after these types of experience to see that they don’t want to go down a career path that they always thought they should.

Obviously, we have vocational schools and then we have schools like a Northeastern that has a work and studying method of co-ops where you get a little bit of opportunity to try some different things. There isn’t this existing experimentation market that’s available to allow people to do internships or job shadowing in a massively scaled way. There’s a gap in the market and leads to people making decisions that then they want to later reverse. That’s separate from your point from a minute ago, Alex about the hobby factor. The people who want to think about doing something that may be is just up until then been their hobby.

They’re in a moment where like, “Can I monetize this? Can I make this my life?” That’s a scary dumb. If you are going to quit your stable career and move to something that doesn’t necessarily give you as many benefits as you had before, you should be a little risk adverse when you make that decision.

Talk about situations where people are contemplating a career change. What have you learned in your work so far about the practical ways that somebody with no connections in an industry can get exposure to something? Whether it’s doing a massage or otherwise.

Using Curiosity And Values To Explore Career Options Intentionally

The most important thing for somebody to do is figure out what they want. What aligns their values? What don’t they like? What do they like? What are they interested in? What are they good at? Find people you’re interested in that are doing the thing that they love or are a potential mentor that has navigated this change or career path before. Be bold and reach out to them. Literally, 10 times out of 10, we get positive responses, especially from hosting.

The most important thing is to figure out what you want—what aligns with your values, what you like and don’t like, what interests you, and what you’re good at. Share on X

I love this. I was just in their shoes. I know exactly what it’s like to make a career switch or reach out to someone online that I don’t know. They are always willing to give their time and information back because it is hard. It’s also super empowering to be able to make that switch. As long as you have the confidence in boldness, reach out to whomever you find online or a mentor that can guide you in the right direction.

Some of the bad questions or the good questions like, how much money do you make, how hard is it, what didn’t you know about this industry that you can tell me now? It’s getting in person and getting a clear view of what you’re getting yourself into is the best way to start. I know all the people that Gabe and I spoke to are always willing to help    and introduce you to more people. They take you on the journey that they went on themselves. It’s such a beautiful flywheel effect where you meet one person. They introduce you to more and then you have this incredible range of network and mentors that you can reach out to.

This question has two parts and it depends on what part of your life that you’re in. If you’re more experienced in your career, your picture of that experience is going to be different than someone who is younger in high school still or maybe just entering college. It is a bit of a different conversation. When you’re younger, you might have a little more of a risk tolerance to try something new than when you are older.

Some basic ways that I’ve seen people just even begin to test interests because it’s all about experimentation. You need to experiment to even identify, “I like this or I don’t like this.” Some ways that I’ve seen people get that very entry level even before internship, school, or job shadowing is workshops. Applying and going to one day workshops in different fields is a very easy access point no matter where you are. It’s typically pretty cost effective as well to test something and do it with your hands.

Aside from that at a little more of a higher-level trade school is something that’s not talked about enough and I wish that it was. It was such a huge influence on me and such a huge part of my life. That’s what we are trying to do with Staj. We recreate what that looks like but in a non-formal setting. Those are some of the ways that we see that exposure to Industries.

Particularly in the trades, where you get a little bit more of a vibe senses feel of what a job is like than you do in an office-based job. As you’ve probably read in the news, as I’ve been reading in the news, there’s a lot more need for people to work in the trades. With AI eating office jobs, maybe we’ll have a little bit of more of a shift to people back into that space.

It’s funny with our stajes that we’ve schedule. We make sure that we schedule the day where there’s something that they could shadow going on so they can get a good idea of what the job is outside of the boring admin work that we all have to do. It allows them to see it’s more dynamic than just boring corporate jobs.

Coming back to this pivot thing for a minute. For somebody who’s trying to make a pivot, what are the best ways for them to demonstrate credibility?

Building Career Credibility Through Curiosity, Initiative, And Exploration

The best thing that our stajes have provided his curiosity because these are such dramatic shifts from what they’re doing. We see a lot of people that are successful in Staj or successful in a career transition is hunger and curiosity to understand 100% of what’s another industry like. To do the Staj experience, reach out to people on their own, do workshops or trade schools. That requires a lot of self-determination and hard work.

All that requires, at least in the beginning, is just as long as you’re curious, hungry and interested in learning something new. That will lead to what your passionate about. If you can find your passion, you do these experiences. You talk to people. That helps you build credibility because you can go into a conversation, perhaps an interview with this experience behind you. I’ve reached out to these mentors.

I have done in-person experiences with these different types of platforms like Staj or trade schools. It proves to the person that you’re speaking to or hiring that you are excited and interested in the thing that you want to do. That leads to a very successful worker. If you are always willing to learn and have the self-motivation to learn, then you’re going to be golden wherever you want to get a job.

Adding on to Alex’s point there. We’ve seen that being more of a well-rounded with access and touch points into different industries and different expertise outside of even what you’re applying for. That does demonstrate the credibility that a lot of these companies are looking for. Even if the things that you’ve touched outside of the role you’re applying for, even if they don’t relate to the things that you’re applying for. Having those well-rounded outlooks in those perspectives bring credibility to your resume.

You’ve got companies who are doing internships. Particularly the ones that do a lot of entry level hiring. They use these summer internships and winter break internships as a way to let people test drive. Also, for them to get a sense of how these people might be as full-time hires. What else would you like to see companies doing to support what you’re doing or to support this idea of career discovery and experimentation?

Careers As Test-Drives And The Importance Of Real-World Exposure

I would love to see them do internships that place people in different roles within the company during the time of that internship. Not just leaving them in this one role during that entire month. I would love to see them work for different roles in that month. If it is a test drive, then let people test drive. It should be a two-way street or a two-way interview almost for that month. Ultimately, you want your people to be working in a place that they’re the most passionate about.

Career Sessions, Career Lessons | Gabe DeSanti & Alex Dworsky | Careers Without Guesswork

Careers Without Guesswork: People can try different roles within that month. If it’s a test drive, let them test drive—it should be a two-way street, almost like a mutual interview. Ultimately, you want people working where they’re most passionate.

 

I completely agree. They also should not just give the interns the work that they don’t want to do. I don’t think that valuable at all. They should let more different roles but also connect with leaders or full-time people in that space. Hear from the people that are doing the job rather than the intern manager.

I think about some of the places that I’ve worked. We’ve had some of these rotational programs weak to weak as you were describing, Gabe. Maybe you do 3 or 4 or 6 months at a pop if it happens to be over your first year or two in a job. People who are in those programs love them because they get to see these different things and work with different groups. They get a better sense of what they think they would fit with.

A lot of times, the groups that are the recipients of these interns want them for longer because they have to invest in getting them up to speed and trying to get something out of them. That’s one of the tensions that exists in all of this is. How can you construct something that gives you a meaningful sense of whether this person might be a good fit for your organization at the same time give them a good view of what it’s like. It’s a hard thing to manage because managers have other things to do including the boring stuff. There isn’t always that perfect opportunity to mesh all of this together and have everybody walk away going, “That was a valuable learning experience for us.”

Completely. There’s a big gap in that market.

Coming back just to the broader idea of career discovery, how do you see things changing going forward? Particularly for this Gen Z population and not far behind them, the Gen Alpha population that’s entering the workforce?

There’s going to be new ways to learn and there’s already new ways to learn. People are learning from videos on the internet. Something as simple as that is going to be something new that needs to be adapted to not only the workplace but to our educational systems. Our education system is designed for generations that were way before us. I just think that the model needs to evolve. I don’t necessarily have to solve for that. In terms of creating new workers, it needs to evolve in there needs to be more access to what work looks like.

It’s a hard problem to solve. It’s not something that the two of you or Staj alone are going to solve even if you’re wildly successful. It’s a societal thing that we’ve got to figure out.

Some of it as we’ve talked about in the conversation is a bit unique to this generation and the dynamics that have been at play over the last 5 to 7 years. Some of it is also just an age-old problem of helping people figure out what they want to do with their lives.

It’s a match between that and then keeping up with the pace of new technology and offerings. What the job market was like ten years ago versus now is vastly different. It’s going to be insanely different in 10 and 20 years. It’s also merging. The age-old question of, “What do you want to do with your life?” With, what tools are available for me? What new job Industries are open that my parents never had access to?

For someone who wants to be more intentional about designing their career, what else besides curiosity would be important to their mindset?

Figure out you actually like. What do you want to do? Do you want to make a lot of money right from the get-go? Do you want to be creative or work with people or work remote? Be crystal clear on exactly what you want, what drives you and makes you happy. That helps you lead in the right direction of what you’re prioritizing and value out of careers. When you are trying different jobs, whether it’s a yes or no. It will lead you in the right direction.

Be crystal clear on what you want—what drives you and makes you happy. That clarity helps guide your priorities and what you value in a career. Share on X

One of the things that comes to mind for me, willingness to be adaptable. This idea that you’re going to be doing one thing or even that you have to do one thing you’re entire professional life. It’s out the window. Being able to constantly be in this mode of thinking about the next year, the next three years, or the next five years and what you want to be doing and how you might have it or how you might want to pivot is going to be something that this generation of people entering the workforce now is just going to have to have deeply ingrained in their heads.

Redefining Career Paths As Experiments And Embracing Micro-Failures

I’ll just add one more thing on top of it. Modifying your thoughts around failure when you’re exploring these different careers. It could feel like a failure if you’ve identified something and then you realize, “I don’t like that.” You feel like you have to start over. A lot of people put a lot of pressure on that decision and just shift. It can feel like a failure. Society can make you feel like a failure for not figuring it out the first time. Ultimately, it is a long journey. That failure is only a failure if you stop there. Taking that and just jumping to the next thing and then jumping to the next thing. Those little micro failures, which is what I call them, are going to lead you in the right direction.

Is there anything that we haven’t talked about that the two of you would want to leave our audience with?

It’s such an interesting time with all these new technologies and insight into other people’s jobs, roles and industries. Take a good look at what makes you happy and what you want to do with your life. Also know that there’s not one career. We live a very long life. There’s a life where you can do three different things throughout your whole career. That’s so cool and powerful to be able to do all these different things and scratch all your different itches.

Our goal at Staj is to help you figure that out and be your career guide. It’s up to you on what you want to do and what makes you happy. Know that it’s not a one-size-fits-all but it’s also that you can do one thing and switch. There’s so many different ways that you can go out there into the world and make money and help people. You need not to limit yourself.

Gabe and Alex, thank you so much for your insights and for the work you’re doing to help people, whether young or old, make better more informed career decisions and contemplate whether they are in the right path and maybe if they want to make a change.

Thank you so much.

Thanks for having us on, J.R.

What should you take away from the conversation I had with Gabe and Alex? First, think of your career less as a single big decision and more is a series of experiments. Instead of trying to pick the perfect path from the outset, look for ways to experience different roles through shadowing, short projects and conversations with people who do the work. Real exposure will give you clarity that job descriptions never will. Second, remember that what employers are often looking for is signs of curiosity and initiative.

More than perfectly constructed career paths, building something, exploring different industries or taking on projects outside your formal role can show that you’re proactive and adaptable. Third, don’t rely on assumptions about careers that you haven’t seen up close. The day-to-day reality of a job is often very different from the way it is described. The more that you can observe and learn from people who are already doing the work, the better decisions you’ll make.

Finally, careers are built through conversations as much as applications. Talking with people in fields that you’re curious about, asking good questions, learning from their experiences could open doors and create opportunities that you’d never find just through a job posting alone. There’s a strong link here to networking and the importance of making it a regular part of your professional activities. I invite you to subscribe to Career Sessions on Apple Podcasts and Spotify. You can subscribe to our YouTube channel. If you found this discussion and lightning, sign up for my membership Community, which is called PathWise and our newsletter PathWisdom. Thanks.

 

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About Gabriel DeSanti

Career Sessions, Career Lessons | Gabe DeSanti & Alex Dworsky | Careers Without Guesswork Gabriel DeSanti is an award-winning content creator, visionary storyteller, and Co-Founder of Staj. Known as the builder of the world’s longest résumé, Gabriel brings unparalleled authority to the exploration and celebration of the world’s most overlooked, unconventional, and extraordinary careers. With a digital presence that reaches over 1.5 million followers, he shines a spotlight on hardworking individuals across industries—partnering with global powerhouses such as the NHL, Remitly, and the City of Las Vegas to champion the value of every job. Through Staj, Gabriel is redefining the traditional internship by creating immersive, hands-on job-shadowing experiences that offer real-world exposure and daily access to diverse career paths. His work not only challenges outdated career narratives but also empowers millions to embrace nontraditional routes, pursue meaningful work, and discover purpose in what they do every single day.

 

About Alex Dworsky

Career Sessions, Career Lessons | Gabe DeSanti & Alex Dworsky | Careers Without Guesswork Alex Dworsky spent her career inside corporate America, seeing firsthand how careers are built—and how often people end up disconnected from the work they’re doing. Along the way, she noticed a consistent gap: people were expected to make life-defining career decisions without real exposure to the jobs, industries, or people behind them.

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