Lauren Keys

Today’s guest retired at 29 by creating a career portfolio that led to financial independence.

Yes, you read that right. And, no, we’re not talking about someone who got lucky as an early employee at a unicorn company, about someone with a big inheritance, or even about a successful entrepreneur with an online lifestyle business.

Lauren Keys started out as a waitress, and launched her career from nothing.

But she continuously leveled up her skills and gradually took on more and more responsibility by being vocal about her interests and skillset, and about how she’d like to grow.

“You have to ask.
I think a lot of times people expect a light to shine down and point to you and say ‘this is the right person for the job’ but sometimes you have to tell them: ‘I am the right person for the job. I can do that for you.'”

Now Lauren is the co-creator of Trip of a Lifestyle, a blog that helps you find your own path to financial independence and adventure.

In this episode Isaac and Lauren talk about how Lauren launched her career by doing cold outreach, how she and her husband avoided lifestyle inflation to reach financial independence, and her work at Trip of a Lifestyle.

Related: Career Crashers Episode 39: Amanda Kingsmith on building a rewarding and flexible career

Also Related: Career Crashers Episode 26: Ben Mercer on Embracing Your Interests

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P.S. Don’t forget to give the show five stars (or six)! 😉

Show notes – Creating a Career Portfolio That Leads to Financial Independence

  • How Lauren defines her career
  • Cold calling/mailing helped Lauren start creating her career portfolio
  • How Lauren found her first job after college by driving around and looking for cool buildings
  • Why having more than one skill matters early in your career
  • Pursuing financial independence
  • How Lauren and her husband were able to “retire” before they hit 30

Connect with Lauren

Full Transcript: – Creating a Career Portfolio That Leads to Financial Independence

Welcome to Career Crashers, where we tell the stories of those who are not content to wait around following rules and hoping for good things to happen. Great careers aren’t found. They’re forged.

It’s time to crash the party.

All right, on this episode of Career Crashers, I am talking to Lauren Keys. And Lauren, I want to ask you to, to introduce yourself. Because I was trying to decide like, I know you have a company called Trip Of A lifestyle. And from what I understand, you and your husband run this company and you are like, retired, but you’re like 29, and you’re retired.

So I don’t know if I should call you the CEO or just like a retired person. How do you introduce yourself?

I’m definitely still putting a lot of work into the blog. But it’s a passion project. So I don’t really feel like it’s the same thing. I mean, I guess CEO is accurate. But to me, I just feel like a blogger, so it doesn’t have the same kind of like gravitas. But in terms of like work that I’m putting in. Like, I definitely I’m still, my husband and I actually launched our blog. Last year, while we were on the road, visiting every National Park and living out of a van, that was kind of our kickoff to retirement, so to speak.

So yeah, a big part of what we try to focus on is kind of similarly aligned to what you like to talk about on your podcast. Which is kind of encouraging people to make their own path. Um, and, you know, we kind of use our story as an example of what’s possible. Like, we took some alternate routes and what that could do for you. And so, you know, a big part of that, for us is encouraging people to become more financially literate, and setting themselves up for success.

Also like, creating a career portfolio is a big part of that. And I think a lot of people, you know, might be might look at when they enter the workforce. Like, wow, working is like such a long time. You know, it’s your career is 30 years, 20 years. And like, you know, maybe you saw your parents stuck in a career for a long time that they didn’t like. You know, it can be daunting. You get to work, and you spend the first couple of years at a desk, and you’re like, this is not what I this is not what I did in college. This is not what I did in high school, you know, I’m used to a little more fun.

And so a big part of what we try to advocate for is like having fun along the way, but maintaining the course toward those goals.

I love that having fun, sometimes gets underrated because rightly so i think you know people who are talking about careers who’ve been successful in creating their career portfolio, talk about the things like persistence and hard work and you know, pushing through and but having fun is like a necessary and an under underappreciated ingredient and kind of following the things that are fun that kind of give you more energy back than you put in. There’s something magical there.

I want to start early with your story. Because I got a few tidbits that are which is why I wanted to have you on the show because I loved in particular, cold emailing and cold calling, which is something that scares the crap out of most people. But you started way back when you were in college. You just sent a letter to a local newspaper. Which is again, we talk a lot about show your work, learn out loud, don’t be afraid to share your learnings. If you have an idea or an opinion, write it down and share it. Like that’s better than just keeping it to yourself.

So you sent this to a newspaper. And they asked you to join as an intern. So that’s kind of the first story. Tell me tell me a little bit about that story. how that came about. And what made you decide, yeah, I’m going to send this into the newspaper, I’m going to share my story.

So I was in school for journalism. That’s what I love that got my degree in. And in undergrad, I was putting myself through college. I had a scholarship for tuition, but everything else was on me. I didn’t have parental help. So I was waiting tables and trying to figure out like, how do I how do I also break into this field and get away from waiting tables, you know, the money was good and everything, but that’s not really aligned with where I want to go.

And so we actually, if we wrote a story for for class, one of our, in our, in our reporting class, we wrote a story and it got published, we would get extra credit. And so that was kind of my like, encouragement to just, well, it’s for school, like, you know, I don’t have to, I can kind of take that blame off myself. I can kind of, well, it’s not for me, it’s for school, so it’s okay, even if it feels weird, like I have to do it, right.

So I think kind of shifting the focus into like, well, it’s first school project. So like, they can’t be mad at me. I’m just asking, you know, for school, so I sent it in. They actually were already writing the story, I think it was something local happening. I don’t know if it was on campus, I don’t even remember the story anymore. But the editor who I sent my story into, told me that he liked my writing. And he said, Why don’t you come on to do an internship, you know, or apply for the internship.

I remember being so nervous going in, to interview with like, an editor, and I like, had my book of, like, portfolio of the stories I wrote for class. And I was like, I hope this is good enough. Then I started that the next semester with an internship. And that internship led into me working there. Quite a few hours, I ended up going, not full time, but I shifted all of the hours that I was working at the restaurant, into working for the newspaper.

And by the end of my college career, I was like, up to almost 40 hours a week doing odds and ends for the newspaper, creating my career portfolio. So I mean, they had different, like, they had a magazine that I also worked for, I did photography for them, like, I kind of tried to do a little of everything to build up those hours. But at the same time, that was building my resume. So like, it was good for the bottom line, and also for resume building.

I love that insight. You mentioned there that, you know, it took a little bit of the fear away of sending in a story because well, I have to and it’s an assignment. I think there’s some interesting ways that you can sort of hack that to get the same psychological effect.

So one thing that I’ve seen a lot of people do, and I’ve done this myself, as well as, give yourself different challenges, like, Okay, I’m going to publish a blog post every day for 30 days, and I have to do it. And then then it’s not really on me if some of them suck. Well, I’m posting every day for 30 days, it’s just part of a challenge. It’s not about quality, it’s just meeting the challenge or Okay, I’m going to agree with a friend. And I’m going to send them you know, whatever a song that I wrote every week or something like that.

And giving yourself some kind of challenge that forces you to do it and takes the pressure off it needing to be sort of worthy of that is, is sometimes really effective way to just start to shift. You said after you graduated, this is how you found your next full time job. You drove around, you looked at buildings that seemed interesting. And you went home and looked them up online. And you just started to you know, you research them and then you just started to go in and apply for positions.

It’s so simple. But I think when creating a career portfolio, a lot of people are kind of waiting for like the skies to park and like a message to come down and say this is the company for you. This is the opportunity. But just the idea of like, Hey, that looks like a cool building. Let me go learn what they do. Let me see if I could work there. And this can apply in in digital world to like, Hey, I listen to Spotify all the time. I bet that’d be a cool company to list to work for.

And like, I love that idea. So tell me how you got that idea. And like what was that process like as you were kind of running that job hunt?

Yeah, so my, when we graduated, my husband actually was going to grad school in California. And I was moving across the country with him. We were were from Florida. And so I was kind of plucked from a newspaper land and going to California and I was like I don’t you know, I have no contacts. I don’t know anyone. And searching online. You know, doing like, Indeed, and looking at job openings, especially for someone who just graduated entry level.

I just wasn’t really satisfied with the results. I had like one call with a salesperson that was like, obviously, like churn and burn type of scenario, or they just like hire anyone. And if you can do it, then you can somehow make a paycheck maybe. I was like, yeah, that’s not for me. And so I was like, I wonder what’s just here. I mean, people live in this area. There’s, you know, business complexes down the street. Like, what are the businesses that are there, maybe there’s something you know, that just they didn’t post it on Monster. They didn’t post it on Indeed, and maybe I could just find it that way.

And so I was driving around and there’s a sign and I was like, it was a studio was in there named DB studios. I was like, What is a? What is that company? They’ve since been acquired. So I don’t mind using it even pointing out this weird fact about myself. But I was like, what do they do? Is it a recording studio? Is it you know, artistic, whatever it is, sounds like it’s probably something for me. I like that kind of stuff.

So I went online, still didn’t really know exactly what they did. But on their careers page, they said, you know, give us a call, we have openings and I was like, Oh, they have openings. I’m gonna give them a call. I don’t know what it’s gonna be for. But we’ll find out. I went in for an interview. Ended up getting their like front desk receptionist job. But that job also included like a bunch of accounting type tasks.

And when I told them that I also had a photography skill set and I could help them with writing. I ended up by the end of my like time with them I had rewritten their whole website for them, written several press releases, started doing a lot of things. Photography in house for them, while also having my headset on from the front desk.

So I took a little bit of what I learned at that paper, which was letting people know, you’re interested in your skill set. And where you’d like to go and grow with the company. If you are vocal about that, a lot of times those doors can be open for you when creating a career portfolio.

You have to ask. I think a lot of times, like you said, People expect, oh, the light to shine down and point to you and say, like, Oh, this is the right person for the job. But sometimes you have to tell them like I am the right person for the job, I can do that for you.

That story illustrates so many, like several points that come up on this show a lot. And then we you know, at Crash, we talked with a lot of, you know, early job seekers about the first of which being, you know, here you are, you’ve got writing skill, photography, skill and interest. A lot of people feel like, Well, okay, I want to go start creating a career portfolio as a photographer, I want to go get a job as a writer.

And early on. There’s a lot of those especially creative fields. There’s very few people that are like, ready to hire you full time for that thing. Because the skill level often isn’t there yet. And so a lot of people kind of are only looking for, you know, content marketing is one today, I want to be a content marketer. And well, if you’re like 22, it’s very hard to get a full time content marketing job.

But what you can do when creating a career portfolio is find a company that interests you. Start with the company, rather than the role, and you kind of found, okay, this company looks interesting. If they have a problem that you can solve, even if it’s answering phones, if it’s customer success, if it’s sales, being a business development rep, go solve that problem. And now you’re in. And you have the ability to say, hey, by the way, I also do photography. I also can write, and when you have an additional skill set, you know, you’re solving it.

Because because they may not have the capacity to bring you on as a full time photographer. But if you can come on and answer the phones and handle the front desk, and then start doing the photography, you can add more and more value and like expand from there. I just think that’s a great a great example.

Tell me about cold outreach. You mentioned in our conversation, or emails, specifically, that this is something that has paid off for you, and you’ve given us a couple examples already. But what are some of the other ways that just cold outreach have been a part of creating your career portfolio? And what do you recommend to other people to make use of this skill that everyone’s afraid of?

Yeah, so it was kind of similar. I tend to approach my job searches and creating a career portfolio, like I do my other work. And I and in that, I mean, I try to be a little bit fearless, a little bit bold.

Because I think that there’s a lot of times we expect to be found. Kind of what we were just talking about putting yourself out there is a big part of that. And so, you know, in my job in marketing. There’s been a lot of times where I’ve had to reach out to people make connections. And, you know, it’s surprisingly, like, gone well. If you reach out to someone, and especially when you’re sincere about it, you know, if you’re asking for someone’s help on something, you know, point out the value that they’re providing for you and offer your value back to them.

Don’t make it creating a career portfolio a one sided transaction. So that’s been something that I’ve I’ve found useful in my general kind of outreach. But you know, I would say that, you know, like I said, in marketing, I have taken on a lot of outreach type of roles. And, you know, it’s really easy to send an email and say, like, Hey, I just wanted to follow up on this, or, Hey, nice job with this, but kind of going the unusual route can work I’ve called people who, you know, have kind of been a little unresponsive, or, you know, they’re supposed to get back to me and didn’t, and it probably feels really uncomfortable to catch someone off guard.

But, like, be nice, like, be disarming. You’re not trying to like catch them or anything. You’re just trying to get them back into the groove. If you were supposed to be working on a project together and they’re not getting back to you by your deadline. This is true for like journalism, too. People don’t get back to you. It’s normal. We all get busy.

Be accepting and aware of other people’s responsibilities when you’re reaching out to them. But reach out in a weird way. Call them. Calling is so like taboo now people don’t think to do it. You know, email is so customary and preferred a lot of times. But if you really need something, especially again, I think layering on the niceness offering.

You know, a good deed in return can really be helpful. And I’ve I’ve found that to be true when people are unresponsive. Sometimes I just got to call them and it works out or find another email, find another person. But just kind of not taking no for an answer until you’re told no. It has been a big part of my success strategy when it comes to outreach and kind of marketing in general.

I love that phrase. You said try try a weird way, like do something weird, be hard to ignore when creating a career portfolio. I love that.

So I want to know about this retirement thing. Tell tell me how, how have you and your husband gotten to a point where you can really focus on this passion project? And was that? Was that a goal you set out to achieve intentionally?

Yeah, so I’d say right after college, you know, we got our first full time jobs. My husband was going to grad school, but he had a stipend. So we had like, income. And then I was working. And that was like, wow, like, what should we do with this extra cash that we have? Because we’re not you know, we’re still living like college students, we’re on campus still. You know, it’s not, you know, we’re not looking to really inflate our lifestyle too much.

And so, you know, we started kind of getting interested in investing in the concept of, well, you know, my money might be able to work harder than I can. What could that mean for us? And so, you know, we kind of got into learning about investing. I came across a news article about a guy who retired in his 30s. Mister Money Mustache, Pita Denny, he’s kind of the father of this movement, called Financial Independence, Retire Early, the acronym fire.

That, you know, maybe you’ve seen a few articles around, it’s, it’s gotten murmurs here and there. And like the financial world, a lot of like, people are concerned about what that means long term for people or the economy. But honestly, it has been, we’ve just kind of followed that traditional path of keeping your expenses low, and taking every spare dollar and just investing it, you know, not inflating your lifestyle.

For example, my husband and I have shared one car between us over the last eight years. We have made it work strategically moving to areas where, you know, we could live close to work to bike if we needed to. Just, you know, being a little bit of planning went into certain decision making about housing, about transportation, some of these bigger picture items in a budget, and then not inflating anything else, really.

And, you know, if I’m happy in college, and that was my lifestyle, then why should it change just because I make more money if I was happy. And so trying to maintain that happiness level, of course, some people have certain things that they prefer, and that’s fine if you can build that into your life. But you know, for us, it was so powerful to think about, well, we could retire before we’re even 40, maybe.

And kind of doing the math on the salaries we had then. And then, you know, not really sure where our salaries would go in the future. We just kind of kept on that train. And anytime we moved, this is like another like secret hack. Job hopping was inevitable when you move. And that has been invaluable for us in terms of increasing our salary. You know, if you’re always working on skilling yourself up, your current job might not be able to compensate you for the leaps and bounds that you are doing in your, in your in your life and your learning and your abilities.

And so, being able to job hop. You can reposition yourself, look for another job, and negotiate into a better salary. That’s what we’ve been able to do a few times when we’ve moved around. We eventually bought a house. When we were 25, we were able to pay cash for our condo here in Florida. And that, again, kind of further decreased our everyday costs. And we were able to save even harder.

I think it’s been about eight years now since graduation. And yeah, we have, you know, enough, saved up enough invested that, you know, we both work on a few freelance part time projects, maybe 10 hours a week or so. And that’s enough to pay our bills, and we’re still saving money. So it just didn’t make sense to keep working as hard as we were when we had things we were interested in.

We weren’t setting out to do a blog or anything like that initially. It just kind of happened while we were traveling last year that we’re like, you know, if everyone knew what we knew, when we knew it, people would be in such such a better position, especially young people, especially our peers. It’s a lot harder to implement an undo button in your life. It’s doable, but it’s harder than not ever like taking those debts on like a brand new car or house that’s too big for you or things like that.

So that’s kind of why we started is to advocate for younger generations who, you know, might want to figure out what they want to do. And if you just work hard, really hard First, you have way more opportunity available to you over the course of your lifetime, for fun, and for passion. And for, you know, whatever else that you want to do with your time.

I love the the point about, you know, career hopping as well as moving. I’ve talked about both of those things independently, as well as together. That like, early in creating a career portfolio, especially the willingness to move, especially to leave your hometown like go where the opportunity is. And then you can you can do geographical arbitrage, as well like to move to a big city that has higher cost of living, but also higher pay for a couple years, and then move to a smaller city with lower costs of pay.

But now you’ve got that salary that you can usually, you know, now you once you’ve commanded a certain salary, it’s easier to ask for that and, and demand that and to look for those opportunities when you can make those jumps, which often, even if it’s a company you love, often you have to leave the company. I’ve seen people leave come in as an entry level at a company, and then leave for a couple years and then come back at a senior level. And they never would have been able to do that if they stayed internal.

It’s really interesting insights and what I’m hearing and tell me if this is incorrect, but it sounds like you have given yourself basically financial flexibility, independence, not by a big inheritance, or building a company and selling it for a windfall or creating a an online e commerce shop that’s just churning out money, but by kind of having a relatively traditional career, but with very, very deliberate choices around spending savings and investing. And and just pursuing that has enabled you to have this freedom. Is that an accurate characterization?

Definitely, I think, and that’s kind of what we want to drive home. We actually, for we hit one year, last month with having the blog and to kind of celebrate, we decided to distill our, our life path into what we think could be doable for anyone else on a middle class kind of salary, to take you from having nothing and maybe just having graduated high school to being retired within like a 10 year span. And it’s like six steps, it includes a step for travel, because we did that a few times when we took six months off and literally lived on a beach in Hawaii as a part of our honeymoon.

You know, and that didn’t impact our ability to make money, our ability to come back into creating their career portfolio, into the workforce. You know, I think a lot of people are nervous about resume gaps and all kinds of things. And so there’s a lot of stuff that kind of people are afraid of, I would say in terms of making unique decisions with with regard to their own life, right, it should be unique. It’s your life. And we’re kind of advocating for, for doing that for figuring out what would what would be powerful for you?

And is there a way you could do it? If the answer is yes, but like, I’m not sure if it’ll work, like just try it. Then you know. And that’s kind of the point in like, calling someone on the phone or sending them a letter or driving by their place of business and asking if they have any career opportunities.

There’s so much good stuff there. I want to I want to point our listeners to what was where is the resource that you mentioned. Where you kind of summarize what you’ve covered in the first year, where’s the best place for people to go and and kind of get started with what you guys are creating on your blog?

Yeah, the best. The resource I was talking about as our financial roadmap, that’s Really easy to get to, but it’s also like, linked to all throughout. So it should be easy to find, if you’re just going and poking around the blog, kind of generally.

But we’ve got articles on you know how to work if you’re a digital nomad how to negotiate with your boss for certain things. You know, what, it’s why it’s important to treat everyone kindly. I mean, it’s you think that that’s like, well, obvious Golden Rule.

But sometimes you’re not expecting the outcomes that happen when you make connections and you don’t know where it will lead. I’ve had random things kind of fall into my lap because of the connections I’ve made over the years by just being like, friendly and trying to you know, connect. And so I would say that there’s a lot of opportunities for people to learn on our blog.

And again, is our blog, and then /roadmap is the way to kind of get from zero to financial independence in six easy steps.

I love it. No, I love it. It’s so funny. Just I mean hearing you talk. Even in this brief interview, there’s so many things that are such as repeat themes in my own life and in the the people that we’ve interviewed on this podcast that you just mentioned, you know, I call it building social capital, but just being kind to people sending thank you notes, people looking for excuses to say thanks, or to point out things people have done well, and just being a helpful, kind person.

The ways that that pays back in the long term are just like, I can’t I can’t even quantify all the things that I’ve done in my life that have been successful, in some fashion have come back to, because I happen to have people that liked me because I had been kind or whatever. You know, like, just those small things that come up time and again, in these interviews, and I’m sure our listeners by now are, are like, Okay, I get it, I see it.

Hey, Lauren, this is absolutely awesome. is the website and I’m gonna go check out some more stuff. This is this has been really great introduction, and I know that our listeners have to be really excited about as well. So keep up the great work. And thank you so much for joining us.

Thanks for having me.

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If you’ve got a story you’d like to share, don’t hesitate! Email Isaac at Isaac [at] Crash [dot] co.

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