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Why You Need a Portfolio Career and How to Do It, with Anne Pryor

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Freelance work is trending, and it doesn’t have to be an exhausting, feast-or-famine career. Your career can prosper as a freelancer if you build a portfolio of skills that can allow you to work on a variety of projects at any given time. Rethink short-term gigs by learning more about portfolio careers.

About Our Guest: Anne Pryor

Anne Pryor is a globally recognized online brand strategist and top 10 LinkedIn trainer. She helps clients stand out, get found, and make meaningful connections for great jobs and profitable business. Anne has written more than 10,000 LinkedIn profiles and trained 100,000 people. 

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Transcript

Find Your Dream Job, Episode 145:

Why You Need a Portfolio Career and How to Do It, with Anne Pryor

Airdate: June 27, 2018

Mac Prichard:

Hi, this is Mac of Mac’s List. Find Your Dream Job is presented by Mac’s List, an online community where you can find free resources for your job search, plus online courses and books that help you advance your career. My latest book is called Land Your Dream Job Anywhere. It’s a reference guide for your career that covers all aspects of the job search, including expert advice in every chapter. You can get the first chapter for free by visiting macslist.org/anywhere.

This is Find Your Dream Job; the podcast that helps you get hired, have the career you want, and make a difference in life. I’m Mac Prichard, your host and publisher of Mac’s List.

I’m joined by my co-hosts, Becky Thomas and Jessica Black, from the Mac’s List team.

This week, we’re talking about why you need a portfolio career and how you can do it.

Many of us may plan to spend our careers working for one employer at a time. But one day soon, full-time jobs may become the exception, not the rule. Author Charles Handy estimates that in a few years, less than 50% of the workforce in the industrialized world will have full-time jobs.

Our guest expert this week is Anne Pryor. She says one way to prepare for this new era of part-time work is to have a portfolio career. Anne and I talk later in the show about the benefits of portfolio careers and how you can do it.

If you’ve been in the workplace for a while, you’ve heard about the gig economy. You’ve also seen freelance work grow in importance. Becky has found an article that looks at the future of these temporary and part-time positions. It says that even CEOs and other senior jobs may soon get filled by gig workers. You can expect new companies to help you find and get these jobs. Becky tells us more in a moment.

You’re laid off from your job. While you look for a permanent position, you take part-time assignments. Should you list every one of these gigs or will you look like someone who jumps from job to job? That’s our question of the week. It comes from listener Kathy Reese in Portland, Oregon. Jessica shares her advice shortly.

As always, let’s check in with the Mac’s List team.

Every week Becky, you’re out there, poking around the Internet, just like Ben used to, looking for websites, books and tools our listeners can use in a job search and in their careers. What have you found for our listeners this week?

Becky Thomas:

This week’s resource has pretty good alignment with the topic you’ll be talking about with Anne today.

I feel like if you’ve been awake and aware in the professional world over the past couple of decades, you know that the nature of work is changing. You’ve heard terms like “gig economy”, and you probably know a few freelancers within your own professional circle.

This week, I want to share an article that dives deep into the short-term, on-demand labor market and the ways that this freelance economy is pushing even the highest levels of businesses to transform. It’s an article from TechCrunch’s Danny Crichton called “Shortly, even the CEO will be outsourced to an online labor marketplace.”

Crichton says that we’re on the verge of a new reality where companies can rent out CEO’s by the hour. It might sound outlandish, but I feel like he frames this assertion with an analysis of how work has evolved over the past decade in a few key stages, driven by the growth and ubiquity of the internet. He broke it down in a way that really made sense to me and made it really interesting.

First we had the free-for-all online marketplace, led by Craigslist and other job boards, where anyone and everyone could post about who they wanted to hire, offer themselves up for hire, or anything that tickles your fancy. Crichton writes, “These were marketplaces built around serendipity, with almost no guidance from the platform on what to charge, how to charge, or how to find the best talent for a particular project.” This was the first step as the internet was really still new and everything was out there.

Next, people started realizing that there were tasks that could be organized around more specific needs. Apps and websites followed the Ubers of the world into more clearly defined, narrow roles. Hourly manual labor could be found on apps like Taskrabbit and customers could purchase set services for a set rate. Taskrabbit would guarantee that the job would get done. This was great for really simple tasks.

Crichton says, “That regularization became the product itself; suddenly the free-for-all marketplace became a tight menu of options with standardized pricing and rating systems. Even more importantly, the identities of the workers themselves are often shielded from the customer on these platforms. You are buying the company’s brand of quality, not the worker’s guarantee that they can do the job.” That’s the second phase.

Now, new companies are evolving to merge the idea of a set menu of work products with the complexity of professional-level work. There are a bunch of startups with names like Clora and Paro and they’re launching products that will pair industry-specific professionals with customers who need that expertise. For example, Clora works with life sciences professionals who can be hired out to launch new medicines, treatments, etc.

In this phase, the professional has a lot more responsibility for the satisfaction of their customer and that satisfaction is a lot less black and white. We all know success can mean different things to different people in business settings. Crichton says designing these online platforms is really important to be user friendly. He writes, “These newer marketplaces understand that professional work is often ambiguous and hard to judge for quality and has built key product features to handle those challenges.”

We’re entering brave new world territory, but as I say whenever I share a future-focused article, I think it’s just essential for today’s professionals to understand what’s out there and what’s coming up.

If you’re on the job hunt, you may already be pursuing short-term and consulting gigs and this article can show you new avenues to get hired. If you’re only thinking about full-time salaried work, there’s still plenty of opportunities to get those jobs, I think, but know that other options are out there, and this is a growing and evolving part of the working world.

It’s a really interesting article.

Jessica Black:

Yeah, really interesting. I think that your comment at the end about just, how the more we can share about how things are changing, because I do think it’s not immediate that this is going to be the norm, but it’s coming. We’ve already seen some inklings of this happening, so the more that people can position themselves well is great.

Mac Prichard:

Agreed and what was striking to me when I was thinking about this and looking at the article too, Becky, forty years ago there was an expectation that you would go to one employer and stay there for fifteen, twenty, twenty-five years. You’d stick with one company. Today, I think most people think they’re going to have a series of permanent jobs that might last three, five, or ten years. At the end of forty years, they might have have seven or eight positions.

What I’m hearing him lay out, and you talk about, is that this trend is you’re going to have a variety of different jobs at once.

Becky Thomas:

Yeah.

Mac Prichard:

You’ve got to be prepared for that.

Becky Thomas:

Yeah, it might not even be those full-time jobs that last for years. It’s those short term projects. I already have people in my network that are doing just that. I think that’s definitely the next phase that’s going to become more and more common.

Mac Prichard:

Yeah and I know Anne is going to talk about that because one way of approaching this trend is portfolio careers. Juggling a lot of different balls at once.

Becky Thomas:

Yeah.

Jessica Black:

I’m really excited to hear what she has to say about that. It’s going to be interesting.

Becky Thomas:

Same.

Mac Prichard:

I am too.

Well thank you, Becky. Do you have a suggestion for Becky? Write her and we may share your idea on the show. Her address is info@macslist.org.

Now, let’s turn to you, Jessica, because you’ve been poking around the Mac’s List mailbag as you do every week. You’ve pulled a message out of the bag for you to answer. Whose letter did you pick this week?

Jessica Black:

This week we have a question from Kathy Reese, here in Portland. It’s also in the same vein of what we’re talking about in terms of part-time work and how to position yourself when you do take on part-time work and looking for that next full-time gig. Kathy’s question is,

“Is it better to list, or not list,some part-time jobs that I have had since I was laid off in July? I don’t want to look like I am someone who jumps from job to job.”

This is, again, a great question and I think it ties in well with what Anne is going to talk about with portfolio careers. I’m really excited for Kathy to be able to hear that portion of the interview as well, but in terms of what my feedback for Kathy is…

I think that you definitely want to list those jobs because you want to be demonstrating that you don’t have a gap in your experience from when you were laid off. I don’t know what type of part-time jobs these are, that Kathy has taken on, if they do tie back into her main career goals. Even if they don’t, I still think that that’s relevant because you can…We’ve talked about this a lot, and I’m a big advocate for, the well-roundedness that you can bring to an organization. That’s really huge.

I would definitely list all of those and I would make sure that you are explaining how they do tie into your ultimate career goals. Again, even if they’re not directly related, there’s always ways that you can showcase that it’s relevant to your end goals.

Also, just staying active. It’s part of the networking process, of getting out there and doing work while you’re looking for that next long-term job. I think it’s definitely okay to say that these were in-between jobs while you were looking for your next career, although I wouldn’t list that on your resume or LinkedIn. You can use that as an explanation in the interview.

In terms of when you do list things in written form, these part-time jobs, I would make sure that you are stating that they are intentionally short, part-time gigs. It’s not meant to be…I think that basically the concern of job-hopping is very valid in this case and in any case. To be able to explain that, I think that, you can just say this was a “short contract”, or you can make some sort of explanation that it wasn’t meant to be a long term, full-time position that you were going to take forever and then you only had it for six months. That can be clearly identified and all employers will understand that language, if it was intentionally very short-term.

If these part-time jobs do fall into your overall career goals, you could list yourself as a type of “consultant”, then break those out underneath that consultant position. That you were taking on these part-time jobs as short contracts but as a consultant. You were lending your services to these organizations. Again, that’s dependant on what kind of jobs they were.

Those are my pieces of feedback. I do think that as we talked about just a second ago, I think that it is more common for people to do multiple things. Again, hopefully these jobs that you’ve taken are maybe not your end goal but are something that can help you in your pursuit of your next job. That way you can explain how these short term gigs, whether it’s consulting, or whether it’s just advancement of skills, and continuation of skills are moving you forward in that.

Number one, I’d love to hear what you guys think, then I can’t wait, like I said, to hear what Anne has to say.

Becky Thomas:

But you still want to hear what we have to say.

Jessica Black:

Absolutely.

Becky Thomas:

It’s not just all about Anne, right?

Jessica Black:

No!

Becky Thomas:

I’m just kidding.

Jessica Black:

I want you guys to weigh in as well because your perspectives are always very important.

Becky Thomas:

Gotcha. Well, I agree with everything you said and I was trying to think of something to add to that. Maybe just the tactical piece, you mentioned how to speak to the fact that these were part-time or short-term gigs and I think it’s easy enough to explain that in the one sentence description of the job on your resume. Then in your cover letter, when you’re applying for the job, be like, “After I left my last-full time position at x, I was excited to engage in multiple opportunities in the meantime.”

Jessica Black:

I think that’s great.

Becky Thomas:

That gives it more context, but yeah, I think that should get her on the right track for sure.

Jessica Black:

I’m glad you said that, I think that’s a great way to both list it on a resume but also give a little bit more context before you get to that interview stage. To let people know exactly what your intentions were.

Becky Thomas:

To be able to go deep on a sentence or two in your cover letter just to let them know where you’re at, where you’re positioning.

Jessica Black:

Yeah. I think that employers understand that people need to make ends meet and that part-time jobs in the interim are necessary just to get by, and pay your bills, and keep things going. Again, if you just provide that context, I think that will go a long way.

Mac Prichard:

Yeah. I think you’ve covered it Jessica. One way I’ve seen people apply your advice on Linkedin, because I’ve looked at a lot of LinkedIn profiles as you know, is that they will list that part-time job and then as you suggest, put it in parenthesis, (contract). If you see a series of those, you don’t think, “Job hopper”, you think, “Oh okay, this is somebody who’s doing relevant work or paying their bills, or both, and they left because it was a contract position.”

Jessica Black:

Right. It does convey that intentionality rather than, you took on a position and six months later you decided to leave because that’s very different in the mind of the employer and for you as well. I think that that’s really beneficial.

Mac Prichard:

Great, well thank you, Jessica, and thank you, Kathy, for your question. If you’ve got a question for Jessica, send her an email. Her address is info@macslist.org. You can also call our listener line, that’s area-code, 716-JOB-TALK – or post your question on the Mac’s List Facebook group.

If we use your question on the show, we’ll send you a copy of our book, Land Your Dream Job Anywhere.

We’ll be back in just a moment. When we return, I’ll talk with this week’s guest expert, Anne Pryor, about why you need a portfolio career and how you can do it.

We all know that first impressions matter. The very first thing a hiring manager sees is your cover letter. That letter gives you a make or break opportunity to wow an employer.

Yet too many job seekers squander this chance. They send a cover letter with typos, a sloppy format, and cut-and-paste text. But avoiding those rookie mistakes isn’t enough to get you an interview. You also have to tell a compelling story.

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Get Simple Rules for a Winning Cover Letter today. Go to macslist.org/coverletter. Start transforming your cover letter today.

Now, back to the show!

Now let’s turn to this week’s guest expert, Anne Pryor.

Anne Pryor is a globally recognized, online brand strategist and top a 10 LinkedIn trainer. She helps clients stand out, get found, and make meaningful connections for great jobs and profitable business.

Anne has written more than 10,000 LinkedIn profiles and trained 100,000 people.

She joins us today from Minnetonka, Minnesota.

Anne, welcome to the show.

Anne Pryor:

Hey Mac, it’s really nice to be here. Thanks for inviting me.

Mac Prichard:

Yeah, it’s our pleasure and today we’re going to talk about portfolio careers. What they are and how to get one. I have to start by asking, ten thousand LinkedIn profiles? That’s huge.

Anne Pryor:

You know, I was one of the first to start LinkedIn online branding, back in 2007, Mac, when I got let go from two jobs in twenty-four months, and I realized the value of that tool to make meaningful connections, and I’ve been helping people ever since.

Mac Prichard:

That’s terrific and it’s important work, and I know as part of that work, you’ve learned a lot about portfolio careers. You’ve got a lot to share from there.

Let’s start with the basics, Anne. What is a portfolio career?

Anne Pryor:

Great question, Mac. I never knew about it until 2007. My career coach asked me two questions that changed my life; number one, “Are you self aware?” Number two, “What are people coming to you for?” I reflected on those questions and I realized that I loved variety, and I loved flexibility, and I loved freedom. She introduced the portfolio career concept.

If you can imagine, it’s like financial portfolios. You might invest in stocks and bonds, maybe real estate, maybe other investments, in cds…A portfolio career is very similar to that. It’s multiple employers. You have no full-time job. It’s part-time or temporary work. Perhaps there’s freelance opportunities. There’s self-employment. You do things that you’re really interested in.

There are four different kinds of buckets. One is giving back, family, leisure, vocation, and then work.

Mac Prichard:

Okay, like in personal finance, you don’t want to put all of your eggs in one basket. What I’m hearing you say in your career is that you don’t want to rely on just one employer alone for your professional success.

Anne Pryor:

That’s right. Now, Mac, you have probably seen the Society of Human Resources report for 2018, and they have the top ten trends and one of the top trends is portfolio careers, another one is work flexibility. We are seeing this coming to life and I think it’s interesting to know how portfolio careers came about. May I tell a quick story?

Mac Prichard:

Please do.

Anne Pryor:

There’s a man named Charles Handy and in 1950’s, he lived in the UK and he worked for IBM. He was a consultant with IBM. He worked with two gentlemen, Michael Hammer, and James Kempty. Those guys were sales guys and what they were frustrated with is the fact that it was taking too long to get their commissions because it was taking too long for their customers to get credit. What they actually did, is they walked the floor to find out what is happening in the process and they got the credit process down from six days to four hours. Because of that, Mac, the re-engineering of society took place and since then more than twenty-five million jobs have been re-engineered by hour.

Charles Handy realized what was going on and he created the term, portfolio careers. He actually began one back then; he was a college professor, he worked for IBM, he did consulting on his own, he did volunteering and he took care of his parents.

He started that concept and he was the first to write books about it.

Mac Prichard:

Do portfolio careers work for all professions or just white collar jobs? Tell us more about that, Anne.

Anne Pryor:

Mhmmm, good question. Portfolio careers can work for any profession. What I’ve found after coaching portfolio careers now for the last ten years is really, Millenials, Gen Z, Boomers, are all over them. Gen X, not quite so much. Any industry, it can work. There are attributes though, that portfolio careerists have that are more successful, than others that don’t have those attributes.

Mac Prichard:

Well, what would you say to somebody who says, “I don’t want to line up three different freelance jobs or have relationships with four different employers. I just want a job.” Why isn’t that a good approach, Anne?

Anne Pryor:

Well, for instance, they need to know themselves and if they know that they just want a job, what I ask them to think about, what is the milestone that you’re at in your life? Do you have kids in college that you have to pay for? Do you have a mortgage yet? Sometimes, Mac, it’s not the right time for people to have a portfolio career if people have assessed their values and done self reflection. There are different components. If it’s not right for them, that’s okay. I have coaches hundreds of people on portfolio careers life and I have found that people want it but they’re not ready because they’re not at the right milestone in their life.

Mac Prichard:

What advice would you give to a listener who now understands what a portfolio career is and is interested in exploring it and perhaps doing it? What’s the best next step?

Anne Pryor:

I’m going to talk about three things.

The first one overarching is, know yourself. In that, it’s know your numbers. Meet with a financial planner and understand where you’re at financially. Can you afford to maybe take a step back or sideways for perhaps two years while you’re getting jump started on this?

The second one is, know your values. Are you risk averse? Are you a self-starter? Do you need security? Are you self-motivated? Do you need benefits? Do you like isolation sometimes because that’s the kind of life. Are you flexible? Do you like variety? Do you have the skills you need? Do you want personal growth? Those are some valuable attributes in a portfolio career life.

Then the third step is, know your characteristics. What are your skills? What are your strengths? What is your subject matter expertise in? I walk my clients through that values assessment, a skills assessment, and a subject matter expert assessment to see if they would be a right fit.

Mac Prichard:

Are there qualities that particularly stand out for people who are successful in portfolio careers that you’ve seen in the folks you’ve worked with, Anne?

Anne Pryor:

Yes, Mac, the best attributes that I’ve seen, people who are self-starters. They’re motivated on their own; they have great coping skills. People that are resilient; they can bounce back quickly. One  of the things that was a downfall for me, honestly, was the organization piece. I’m an abstract, an intuitive feeler, so the organization stuff, I had to hire somebody to do so for me. The scheduling piece.

The other thing, Mac, is you can’t be a perfectionist in this lifestyle. If you are, maybe you need to take a step sideways there. High energy is great, to be a learner. One of the most important things is that they need to enjoy networking because it’s always about three things in the pipeline at all times. One of the tools that I coach on is how to create an advisory board and find an advisory board of influencers. I have an AD 33 strategy that I coach my clients on so that they get referrals from all those different components of their career.

Mac Prichard:

Good. Well, let’s talk about both the benefits and the risks of a portfolio career. Let’s start with the benefits. I think you’ve touched on a few of these, Anne, but can you tell us what people can expect? What kind of good things are going to happen if they take this approach?

Anne Pryor:

They are going to really enjoy the variety in their life, they’re going to be able to use all of their skills, they’re going to be able to choose the kinds of people, the kinds of clients, that they want to work with. Honestly, there’s no boredom in this kind of a lifestyle. They are going to grow personally and professionally. It’s a significant benefit and the freedom feeling is wonderful. Those are some of the benefits to this lifestyle.

Mac Prichard:

Okay. What kind of risks should people be comfortable with if they’re pursuing a portfolio career?

Anne Pryor:

One of the risks is a financial risk up front. If they do not have a steady income coming in, what I invite my clients to do is actually work somewhere ten to twenty hours. With twenty hours, perhaps they could get some benefits covered, and then they’d have a consistent income with that twenty hours a week. That would be a risk, perhaps is the benefits.

Isolation could be another one. That has been overcome quite easily with these co-location workspaces. My portfolio careerists rent a space for $70 a month, they can pop in, and then they have the social networking that they desire.

Mac Prichard:

Are there people that you recommend not consider a portfolio career; it would just not be a good fit for them?

Anne Pryor:

Mac, the ones that I’ve found are the people that are too afraid to take the step, and the people who have too much debt, and they are looking to the future and they are seeing that they cannot pay it off because they need that steady income. It’s mostly the financial piece that is precluding people from stepping into the portfolio career life.

Mac Prichard:

Okay. Well, it’s a terrific conversation Anne. Thanks for laying this out for us. Now tell us, what’s coming up next for you?

Anne Pryor:

I’m coming out with my Freedom Plan Portfolio Career Life: Be Inspired and Do What Brings You Joy, and that will come out later this fall.

Mac Prichard:

Good, well I know people can learn more about you by visiting your website, that’s annepryor.com. Congratulations on your book. I’m sure it’ll be on your website as well, won’t it?

Anne Pryor:

Yes, it will.

Mac Prichard:

Okay, well thanks for joining us today, Anne.

Anne Pryor:

Thanks Mac, I really appreciate the time.

Mac Prichard:

It’s been a pleasure. Take care.

We’re back in the Mac’s List studio with Jessica and Becky. What were your takeaways from my conversation?

Jessica Black:

That was great. She had so many good pieces of information and a great explanation of what portfolio careers are and that anyone can utilize it. It’s not just for one specific person and I really liked all of her information about the pros and cons of taking that on. You have to be aware of what you’re entering into. One thing in particular, you can’t be a perfectionist, I thought that that was really interesting.

Mac Prichard:

I liked that, too.

Jessica Black:

Yeah, and her focus on making sure that you are financially stable enough to do that. It’s completely different; if anyone has ever been a consultant, or a freelance person, you don’t have the benefits of benefits, or the stable paycheck every month or every two weeks or whatever the cycle is. It can fluctuate a lot depending on high times or low times. You do have to focus on that networking side of things.

I thought it was really good for her to lay all of that out so that people know what they’re getting into. Overall, it was just really good.

One thing that I do want to point out as well was when she came off the interview and we weren’t recording anymore, she gave you some very concrete pieces of advice for your own LinkedIn.

Mac Prichard:

She did, didn’t she? I think she had a long list, which I’m grateful for. I asked her for the top three. What did you two think of her three tips?

They were, that on my LinkedIn profile, I encourage listeners to go and check it out, maybe I will have updated it by the time this airs. She said I needed a background photo, that was a lost opportunity. The second was that I was creating lots of media like this podcast and she couldn’t find it on my LinkedIn page. The third was that I needed to make my summary statement more personal. She knows I grew up in Eastern Iowa, and of course, she’s from Minnetonka, and she said, “You should talk about that experience.”

Jessica Black:

How it shaped you and your values, and what’s come out of that. It was really interesting but what I got out of that was that even someone who’s one of the most well-connected people in Portland, Oregon, and probably beyond, you have a really robust network, but even someone who’s very well known in the community, or in your industry specifically, still has room to grow. There’s always improvements that can be made to help you share your best story and put yourself in that best light.

Mac Prichard:

Yeah, I welcomed her suggestions; they were spot on.

Becky Thomas:

Good. I just thought she was so empathetic and warm, in the interview and I really appreciated that. Just the advice about the types of people that are going to do well with portfolio careers are those self starters and those folks that love variety and love freedom and are willing to go take those risks and enjoy the networking piece. I feel like some people, if they don’t enjoy that self-starter, they need direction, or they need more structure, they might not thrive in that type of career, but for some people it’s so great. I think the focus on knowing who you are and what you need from your career is really central.

Mac Prichard:

Yeah, I too, was glad that she was candid about the risks of a portfolio career, and clear that it’s not for everybody, but she did, I thought, a good job of laying out the qualities of people who are successful.

Becky Thomas:

Yeah.

Mac Prichard:

It’s a great option to have. I’m looking forward to her book, which, this show airs in June of 2018, but the book comes out this fall and I know it will be on Amazon and I can’t wait to see it.

Jessica Black:

Yeah, it’ll be great.

Mac Prichard:

Terrific, well thank you both, and thank you, Anne, and especially our listeners who downloaded today’s episode of Find Your Dream Job.

Don’t forget to make the most of your job applications. Learn how to write the perfect cover letter. You can do it.  Get Simple Rules for a Winning Cover Letter today. That’s our new resource at Mac’s List and you can find it at macslist.org/coverletter.

Join us next Wednesday when our special guest will be Nella Barkley. She’s author of The Crystal-Barkley Guide to Taking Charge of Your Career.

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