The Rise of Portfolio Careers: Is It Your Path to Success? S5E03

Is the traditional "career for life" concept outdated? In this episode, we are exploring the rise of Portfolio Careers.

Listen in to discover what a portfolio career is (it's more than just a "side hustle"!), why it's becoming so popular for both companies and individuals, and how it can offer a "risk-free" path to finding your calling. We'll break down all the pros and cons to help you decide if this flexible, multi-stream approach to work is the right move for you.

🧭 Is a Portfolio Career Right for You?

Take our free, 12-question quiz to get a snapshot of whether this path is a viable option based on your personality, dreams, and current situation. You'll get an honest answer and a simple action step to move forward!

https://discoveringyourcalling.com/quiz

💡 What You'll Learn in This Episode

• What is a portfolio career? (We break down Anna Mackenzie’s definition).
• Why is this trend so popular? (Hint: It’s a win-win for companies and employees).
• The 3 main advantages for your wellbeing: (More creativity, no boredom, and using your natural talents).
• The key financial advantages: (Building a safety net, diversifying income, and creating a "risk-free exit strategy").
• The 5 main disadvantages to consider: (No traditional benefits, juggling multiple things, and company policies).

📚 Resources & References

• Anna Mackenzie's Substack: Anna Mack’s Stack
• The Portfolio Collective: What Is a Portfolio Career?
• Upwork Study: Portfolio Careers Offer Flexibility & Income for Gen Z
• Snaphunt Trends: Future of Work 2026—Key Trends

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Let’s continue the conversation beyond the podcast.

🔗 Connect with Sheri

 Facebook & LinkedIn: @SheriMiter

Website: www.sherimiterco.com

Additional Resources:

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Matthew 5:14-16 is the inspiration for this podcast.
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Transcript

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SPEAKER_00 2:01

Hey there and welcome back to the Discovering Your Calling podcast. Today we are talking about something I've been hearing and seeing a lot, and you may have as well, and that's portfolio careers. And inside today's episode, I'm gonna break down what is a portfolio career, why is it becoming so popular to create a portfolio career? And most importantly, is this the right move for you? And you might just say, I'm a little obsessed with portfolio careers right now. And you'll find out why inside this episode. Let's jump in. Welcome to the Discovering Your Calling podcast. I'm your host, Jerry Miter. I'm here to help you unleash your strengths and get clarity on your calling. I believe when you find your purpose in life, fulfillment, joy, and success will follow. If you're ready, pop in those earbuds, hit that follow button, and join me on this journey toward discovering your calling. So as I said in the intro, I have become a little obsessed with this thought, and this, I don't know if it's not really a thought, it is a thing of portfolio careers. I'm a little obsessed about it because I really see the value of someone like you who's thinking about creating their calling or wants to create their calling. I feel like the idea of a portfolio career could be the answer for you to discover your calling, create your calling while still having the safety net of a nine to five secure job, or maybe it's another business you're running now, but you want to create something new that feels more aligned with your calling. And there's just so many other benefits to it that I just feel like it could be the answer for so many people. And I want to jump in and really, you know, stick to the facts today as much as I can go on a whole tangent of my thoughts on portfolio careers. I want to give you some real tangible um advice, some real tangible stats, some real tangible thoughts that you can hold on to to figure out is this actually the right move for you? So, as I shared, we're gonna break down what is a portfolio career if you're just now hearing about it and why is it becoming so popular? And it then again, of course, is it the right move for you? So let's jump in. What is a portfolio career? Well, I love Anna McKenzie's definition of a portfolio career. She says a portfolio career is having several part-time jobs or multiple income streams rather than one full-time gig. In her mind, it has two defining characteristics. One, it involves pursuing multiple passions, interests, and types of work. And two, it's never static. It's always evolving. She goes on to say that a portfolio career can include a part-time job, maybe something you work three days for another company, a part-time business, maybe it's three days a week of your own company. Maybe it's a done-for-you service like contracting or consulting that you're offering. Maybe it's a done with you offer, like coaching, mentoring, or advising. Maybe it's a do-it-yourself offer, like a digital product or online course that you offer. Maybe it's creative work, like writing, podcasting, TikToking, playing music. Maybe it's giving back giving back by volunteering or doing pro bono work on the side. And it really could just be a mix of any or all of the above. Now, I first heard about portfolio career careers when I heard Anna actually speak on another podcast. And that was where I went down the rabbit hole of portfolio careers. And I found Anna Substacked, which I'm really obsessed with right now. And I'm gonna put her Substacked in the show notes along with all the other um research links that I use, the resources I used for this episode. So if you want to go down the portfolio career rabbit hole after you listen to today's episode, there's a ton of links you can do that with um in the show notes. But if you're curious about Anna's uh Substack, it's under Anna Max Stack, which by the way, Substack's also becoming something I'm a little curious about, but that's for another episode. But anyway, back to career portfolios. So if you're like me, you might be thinking, well, gee, Sherry, it sounds like what we used to know as a side hustle. That's what we called it back in my direct sales days. When we were recruiting women to join our team, it was more of start this as your side hustle. That was the language we used back then. To be perfectly honest, I never liked that verbiage, and I definitely don't like it today because who wants to hustle, right? We may want a side career or side business, but I think the idea is to get away from hustling and doing more of what gives us fulfillment and freedom and joy, not more hustle. It's not about building something that's just going to make you busier than you already are. There's a reason behind creating something else on the side. Now you may also be thinking it sounds a lot like a passion project. And if that's your mindset, then you're absolutely right. It's really about creating something that fulfills you, it's something that uses your gift and talents and strengths. Hello, discovering your calling, right? And it gives you that opportunity to do something else that lights you up. And that's why I think it falls in line so beautifully with the concept of discovering your calling. If you've listened to or you read my book on Discovering Your Calling, you know some of the things we talk about inside the book and inside the Discovering Your Calling Academy, is that you can start creating something on the side while still continuing to work your nine to five job. If you know my story, that's exactly what I did. I stayed with my direct sales business for almost two full years. It was like a year and a half before I actually stepped away from it. And in fact, I didn't know it then, but I see it now. I was building my portfolio career. And I'm still love this concept because inside my own business, I like the idea that I can, you know, work on the Discovery and You're Calling Academy part of my business and offer that to my clients. But yet over here, I can do workshops for first responders and fulfill that part of my business. And I can work with sales teams on another piece of it. And I can do some other things as well. It's about creating this full life around work that lights you up, work that uses your gifts and talents, work that takes the skills that energize you and put them to use to help others. Work that doesn't feel like work sometimes. And it's also, as I teach in my book, it's a way to kind of almost create a risk-free way to create your calling. Now, nothing, of course, is totally risk-free, but I think it's a safe way to do that. It's kind of stepping into it without feeling like, oh, in order to find my calling, that means I have to leave behind everything I've built up to this point. And it's not about that at all. And that's one of the reasons why I just feel like this portfolio career concept is just the perfect mindset to have as you start discovering your own calling. And this concept is really not just something that I'm obsessed with, but there's actually stats behind why it's becoming so popular. So let's jump into that. Now that we know what a portfolio career looks like, let's talk about why it is gaining so much popularity today. Well, first of all, it makes perfect sense for the companies that maybe are taking advantage of people building portfolio careers. And of course, for the person that is building a portfolio career. So let's talk about the advantages for companies out there. The cool thing is they can hire a person as a fractional employee instead of a full-time role when they take advantage of somebody doing consulting on the side, when they take advantage of somebody doing um maybe offering a service on the side, they can hire them in to take care of that specific thing instead of having to hire a full-time employee to fit that need. And what that means for the company is they don't have to provide a full benefit package. They just pay for that person's services when they need it. So it might be strategic consulting. That's another piece that I love to do for businesses is strategic consulting. So they hire somebody like myself to come in and help them with that project. And then that's the end of that relationship until they need it again. Maybe it's like the IT person. Instead of having a full-time IT person, they have an IT person that comes in when they're needed. Um, so for the company, it's really a smart way to do things without having, if they don't have the the um income to hire somebody full-time for that position, it's a way for them to get the service without having to do that. It also is beneficial for companies to look at hiring uh these portfolio career type people because it enables them to have more global expertise more easily. You know, with the internet today is like we could be, you know, working with somebody in a whole, you know, across the globe that can help us with whatever it is we need. So it really enables us to tap into global expertise. So a company can have that global expertise without again having to hire a full-time employee. So the other benefit for the company is it keeps costs low while they can try out new things. Maybe a company or organization wants to test something out and they just want to see what it looks like, see how it works. So they can bring somebody in to help them with that need right then and there without, again, having to hire a full-time, you know, having a full-time role for that person. It also, the part I really love is it really enables a company to bring in more mentors, coaches, and consultants as needed. Um, a lot of executive coaches really would be considered having portfolio careers. That's a piece of their portfolio career. They work with the employees as needed. So, those are some of the benefits for a company to look at people who are building portfolio careers more seriously and to use them to benefit uh the company as well as helping out that person build their side business. So, what are the benefits for you? If you decided you wanted to build a portfolio career, what's the benefits for the person running that business? Obviously, it gives them a chance to have more income because you're in control of what you're paid. As a consultant, running your own business, you could probably make a lot more money versus being an employee. It also lets you have more flexibility. I think about nurses or I have a lot of physical therapy friends that work per diem. It's kind of the same idea. You can pick and choose when you want to work and what projects you want to take on. If it doesn't align with your values or your works, your time schedule, or um, you know, the type of company you want to work with, you can say no. You have that flexibility and total control over who, what, when, where you're working. It also just gives you a lot more control over your career and the trajectory that you're going to take your career. Maybe there's things that you want to explore that your existing company won't allow you to explore. When you create a portfolio career again, you're free to choose whatever direction you want to take it. The other thing, and I already touched a little bit about this earlier, that I love about the idea and concept of creating a portfolio career is it really enables you to have a safety net because you could have part of your portfolio career could be staying in your existing nine to five career right now. But then you have this freedom and flexibility to build something on the side that lights you up. And I know that sometimes you think, oh, but that sounds like so much work. I'm already so busy enough. I don't have time for that. But here's the thing, and this is how it ties so beautifully in with discovering your calling. If that extra thing is something that uses your natural strengths, it will energize you. It will give you joy. You'll be excited to do that. So you will gladly exchange perhaps watching the latest Netflix show or scrolling Facebook or doing some of the things you're now doing that keeps you so busy. You'll happily exchange that time to create something that lights you up, something that feels like you're using your God-given gifts to help others. And more on that in a minute. So it gives you that safety net. So again, some of the reasons that why an individual might want to create a portfolio career, it gives them more income potential, more flexibility, more freedom over how and where and when they're working their careers. And it also gives you an extra safety net to have something on the side. The other part of that safety net, and this is something that I think is super, super, super important right now in today's um economic environment, is there are no safe careers right now. Like nothing is safe. And in my mind, I think everybody should be creating something on the side that's theirs. Something on the side that if God forbid, tomorrow you go into work and they tell you, sorry, we have to lay off, you know, 100 people, a thousand people, 10 people, and you happen to be one of them, you'd be okay because you've already started creating this other thing on the side that you can just build bigger, but you already have it started. You're not starting from scratch because if you've ever started any type of business, it takes a while to gain traction. So gain traction now, while you have this supposed secure job over here, start building your side business, your passion project that can be there if that time comes when God forbid the rug's pulled out from underneath you and you no longer have what you thought was going to be your career for the rest of your life. And I'm even seeing that happen a lot in the direct sales industry. Um, a lot of my friends that work for other uh network marketing companies, their companies have closed, like they were open today, they're closed tomorrow. Like that quickly things can happen. So, in my mind, everybody should be creating their own portfolio career. It is the only safe way to have financial security in the future. But the key is to create something that fulfills you, something that gives you joy, something that uses again those gifts and skills, life experience, everything you have rolled into one. And that's where my discovery in your calling academy comes in. That's where reading the book comes in, so that you can create that. That was my soapbox about portfolio careers. Didn't intend to go there, but it's the heart of what how I'm feeling right now and why I really am obsessed with this concept. So let's get back to some stats. For those of you that like the stats, one article that I researched, and like I said, I dove in and I went down the big rabbit hole of research for this episode. Um, they said the concept of having a career for life is outdated. Having just one job forever, that's falling out of vogue for a good reason. And here's the stats behind it the freelance market, which freelancing would be a type of portfolio, something to add to your portfolio career. The freelance market is projected to grow by 15% every year through 2026. And by 2027, over 86 million Americans could be freelancing. What could you freelance, my friend? What skills do you have that where you could freelance? Here's another stat: a record 8.9 million US workers already held multiple jobs in 2025, the highest since 2009. There's a lot of people diversifying their income streams. Now, a lot of that is out of need, but a lot of that is out of want. Here are a few more stats. 50% of all workers and 71% of high performers plan to launch a portfolio career. That's from Forbes. 53% of Gen Z workers are already working full-time hours across multiple freelance projects. That's from Upwork. 36% of U.S. adults earn money beyond their main job. That's from bank rate. And nearly 45% of workers have a, there's that word, side hustle. The freelance economy is exploding with 59% of freelancers earning over $100,000 in 2025. And that number is expected to continue to grow exponentially. It could also be a way to find fulfillment and purpose through a hobby or service while working in a career that you only have a few years left in before you take an early retirement. Imagine this. Maybe you only have two or three years before you can officially retire from your job, collect your pension, get all the benefits that you've worked hard to have, stay there, don't quit, don't walk away from that. I would never encourage anybody to do that. But maybe you're just yearning for something else on the side, a way to give back to society. A portfolio career may look like for you a hobby that you can take your skills, again, your life experience, you can freelance in a way to give back to somebody. It doesn't necessarily have to be about having another paid gig on the side. And for some of you who are just starting on the opposite end, who are just starting, just like one of the stats said about Gen Z workers, they're working full-time hours at multiple freelance projects. So they might be doing this today and that tomorrow and another job the next day. But together they work 40 hours. It's just a mixture of different things that light them up. So you can see there's just numerous possibilities with the concept of creating a portfolio career. To me, it's all about letting go of the traditional mindset of what a career should look like and being open to what it could look like for you. And that leads me into the last part of today's episode. And that is, is a portfolio career right for you? So I want to tell you some of the advantages of it and some of the disadvantages of it. So the advantages of creating a portfolio career, there's three big advantages I thought of at the top of my head that have to do with your well-being. I think a portfolio career could be a great way to let your creative juices flow. I don't think we do that enough anymore. We don't do things that are let our creative side out. Um, we're so stuck, and especially with AI and things like that, we're not being creative anymore as humans. And maybe you have a gift of painting. Maybe that could be your side project. Maybe you have a gift of writing. You've always wanted to write, write. Maybe you could start a blog. Maybe you could start your own Substack, a different place to put a blog. Maybe it's just a way that you can just be more creative. That's so good for your well-being. The other thing is you won't get bored when you have a portfolio career, which again is a benefit for our well-being. Because boredom can lead to depression. So if you are depressed, my friend, and you're falling into that depression realm, a lot of times that happens because we have too much time on our hands doing the same old, same old, and we're scrolling through social media, watching everybody else have, you know, quote unquote life while we feel like we don't have a life. So if you feel like you're depressed, it's probably it could be a lot from boredom. So when you create a portfolio career and you do it the right way, you won't be bored. And again, it can be a way for you to use your natural God-given talents and skills without feeling boxed in. Again, so good for your well-being. Now, the financial advantages of creating a portfolio career is again, I can't say this enough. You can ease into it while still keeping your nine to five job. You're building a safety net and diversifying your income. Again, there is no safe job out there. So start building that safety net today and add to your income. What would you do with some extra income? We didn't even talk about that. Would you buy an RV? Would you buy a boat? Would you travel more? Would you buy that vacation home? Would you pay off some debt? What would you do with that finite with that extra financial? Would you just create a bit huge safety net for yourself? Another financial benefit of creating a portfolio career is it's a smart way to reduce the risk. If one income stream dips, you still are covered. We've talked a little bit about that already. Another benefit right now is another new term I was introduced to recently was job hugging. And job hugging is holding on to that job we really don't enjoy anymore, but you're holding on to it for security reasons. And I feel like stepping outside and starting to create that portfolio career is a way that you can still job hug while you create this side thing to start taking back control of your career in your life. And again, it's part of your risk-free exit strategy that I talk about and the discovering your calling book. It's a piece of it to do that, a financial piece of it and a smart piece of it. Now, what are some of the disadvantages of creating a portfolio career? Because it's not for everybody, and I don't want to pretend like it is. Um, some of the disadvantages of, of course, you would not have traditional benefits like health insurance. Now, if you are a full-time portfolio career person where you just have a lot of different freelance, a lot of different options, but they're all under your own umbrella. Um, there are ways to get health insurance, of course. There's a way to secure yourself, there's a way to create your own retirement plan, but you would not have the traditional benefits of a company giving those to you. Another big disadvantage that I think you really have to look at is you do have to be somewhat good at juggling multiple things, because it does mean that you would have to, you know, take the time to create something, take the time to build something. And that would mean, you know, what can you give up in order to, you know, create this? It would mean that sometimes you have to um, you know, wear multiple hats at one time, or you know, multiple hats throughout the week. And for some people, that just is very stressful. So if that's you, it may not be the right path for you. Another um disadvantages, disadvantage of a portfolio career is that it might take longer to see success. In building a business, usually the thought is to follow one course until successful, to stick with one plan, one client, you know, one ideal thing, you know, one idea until it's blossoming and blooming and you know, successful before you start creating other, you know, other pieces of a different business. So it there is a reason behind that concept, and that is definitely the fastest way to success in business. So it might slow down your success if you're diversifying too much too quickly. Um, another disadvantage is you do need to market yourself effectively so that everything makes sense together because you don't want to seem too scattered. You don't want to seem like, what the heck is she doing? This is a fear I have. It's like, what is Sherry doing now? Yesterday she was, you know, over here and today she's over there. And you don't want to give that perception. You want to give that perception that it all makes sense and that you are, you know, marketing yourself as this person who can do multiple that does multiple things for a reason. So you have to be kind of careful in how you market yourself so you don't just become this flighty scattered person that nobody's gonna work with you at on any of the levels because it just doesn't make sense to them what you're doing. The last disadvantage that I have for you today is that if you are working another corporate job right now, you do want to be mindful of your company's policies. Um what rules do they have about you creating, you know, a consulting business on the side or freelancing on the side? So definitely check into that, talk to HR, be respectful of that, and make sure that you're not jeopardizing your nine to five job if this is going to be something you do on the side. So just be mindful of whatever the policies are where you do work. Here's my honest take on it. If you have a hobby or a skill or something you're just passionate about that you could monetize and you have the time to do it, why the heck not explore it? Why not look to see if you could make a little extra money um doing this on the doing something on the side? I mean, to me, there's just not a lot of reasons why not to. Now, if by now you're thinking, all right, this sounds kind of interesting, but I just don't know if it's right for me. I have you. We've got you. I'm excited to say that we created a quiz, a portfolio career quiz to help you decipher if it is, in fact, the right time for you to start creating a portfolio career, or maybe not. And this quiz is just 12 quick questions that they'll give you a snapshot of whether it's a viable option for you based on your personality, your dreams, your current situation. And after you take the quiz, you're just gonna get a little blurb with an honest answer of where you fit in there. There's four possibilities. And no matter what level you land at, they're gonna have um a simple action step that you can take to help you move forward and gain more fulfillment, freedom, and joy in your career and life, whether it's through a portfolio career or stay in the course where you're at. Um, so definitely worth taking the quiz. And you can take this free quiz at discovering your calling dot com slash quiz, forward slash quiz. I used to call it a backslash, and I was just informed that's actually a forward slash. So discovering your calling dot com forward slash quiz. The link will be in the show notes as well. But head over there, take the free quiz and see whether or not it is the right time for you to start thinking about creating a portfolio career career. And if it is, you know, your first action step to get the ball rolling. And one more thing, if you are curious to learn more about creating a portfolio career, then join me back here in one week for a bonus podcast episode. I'm normally doing these every two weeks, but I'm gonna throw out this bonus episode next week because I'm gonna break down five things you can start doing right now to start creating your portfolio career before. 2025 ends. So it's quick action steps you can take, things you can start working on, things you can start doing to actually create your portfolio career if it is the next best move for you at any level, whether it be as a hobby, whether it be as a side project, a passion project, or whether it be like, hey, I want to go full in and I just want a portfolio career as my career. And that's all I want. And in the meanwhile, I know we covered a lot today. So I would just love to know what are your thoughts on the portfolio career? Yay or nay? What do you think? Is it for you? Do you think it's a good idea or not so much? And as a reminder, take the quiz and also check the show notes for all the resources that I use to bring this episode to you today. Thanks for listening and we'll catch you back here in one week. Thank you for spending this time with me. My hope is something you heard today inspires you to take action toward discovering your calling. I just have two favors to ask of you before you go. One, if you found value and enjoyed this episode, please leave us a review on Apple Podcasts or Spotify, and you might hear your review read on a future episode. And two, can you share this episode with three friends who will also enjoy it as much as you did? By doing these things, you will help us grow the podcast to make a bigger impact on the world. And until next week, remember, you've been created to live a life of fulfillment, freedom, purpose, success, and joy.