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Reinventing Your Career, with Michelle Hynes

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Everybody knows that changing jobs regularly is the new normal. The days of working for just one or two employers through your adult life are long gone.

But what about switching not just jobs, but starting a new career? Most of us will be in the workplace for four decades or more, so it’s a choice each of us will face. In fact, we may have three or four distinct careers over the course of our working lives.

This week’s guest, Michelle Hynes, is a career coach who has, herself, has gone through several career changes. She shares her insights on how to reinvent yourself, not just to improve your marketability, but also to increase your happiness.

This Week’s Guest

Michelle Hynes is a certified coach who helps people navigate planned and unplanned transitions at work. Her clients are people who care deeply about how their work serves the world around them and want to grow their impact with integrity and ease. Before moving to Portland from Washington DC, Michelle spent more than 20 years in the non-profit sector as a program director, a board member, and a volunteer

Resources from this Episode

Transcript

Mac Prichard:

This is Find Your Dream Job, the podcast that helps you get hired and the career you want and make a difference in life. I’m Mac Prichard, your host, and publisher of Mac’s List. Our show was brought to you by Mac’s List and by our book, Land Your Dream Job in Portland and Beyond. To learn more about the book and the updated edition that we published on February 1st, visit macslist.org/ebook.Everybodyknows that changing jobs regularly is the new normal. The days of working for just 1 or 2 employers throughout your adult life are long gone. What about switching not just jobs but careers? Most of us will be in the workplace for 4 decades or more so it’s a choice each of us will face, especially when we reach the mid point of our career. This week on Find Your Dream Job we’re talking about how to change careers, especially in mid-life. We start with Ben Forstag will tell us about a non-profit that places experienced professionals and fellowships with social change organizations. Cecilia Bianco tells a reader her advice about how to navigate a career change and I speak to this week’s guest expert, Michelle Hynes. Ben, Cecilia, what’s a career you 2 hope to try later in life, or maybe several careers?

Cecilia Bianco:

Well, I’ve always hoped to eventually move into being an author. Maybe a non-fiction book or fiction.

Mac Prichard:

Good. A young adult novel?

Cecilia Bianco:

Possibly. Those seem to be popular these days, but I don’t know.

Mac Prichard:

Okay. That’s a side of you I didn’t know about. That’s fascinating.

Ben Forstag:

I’ve got 2 different visions for my professional future. One of them is getting really deep into statistics, especially sports statistics because there’s this burgeoning field of statistics around baseball and inferring information from the data that I think is really interesting.

Mac Prichard:

There’s a great book, Moneyball, by Michael Lewis.

Ben Forstag:

Sabermetrics. The other vision I have for myself is the more artistic one, which is just becoming a freelance painter trying to sell my paintings. I think that vision might be reserved for retirement.

Mac Prichard:

I didn’t know about your painting. I certainly have seen your fascination with statistics at work here at Mac’s List.

Ben Forstag:

I have a couple paintings in my office. I’ll show them to you after we’re done recording today.

Mac Prichard:

Okay. I’ve actually been to your office, so I’ve seen those paintings.

Ben Forstag:

They’re pretty small paintings so you might’ve missed them.

Mac Prichard:

I don’t want our listeners to think that we never go into each other offices or the Mac’s List empire is so vast that it’s too far to travel between our offices.

Ben Forstag:

Well, you do sometimes hear an echo in your office, Mac, it’s so large.

Mac Prichard:

Yeah. As for me, I think about what I might do in my 60s and 70s and I think it will involve writing and there are some personal projects I’ve wanted to work on, family history, for example, that I hope to turn to. Like a lot of baby boomers, I think I’ll be working for well into my 60s. I’m actually excited about that possibility. Let’s turn to Ben, who every week is out there searching the internet looking for resources and tools that you, our listeners, can use. Ben, what have you found for us this week related to our topic?

Ben Forstag:

This week I want to talk about an organization called encore.org. This is a San Francisco-based non-profit. Their basic job is helping older professionals, folks who have had their first career, often in the for-profit sector, transition and start a second career, or an encore career, for a social service organization. Is this an organization you’ve heard of before, Mac?

Mac Prichard:

It is. Coincidentally, the founder of encore.org was in Portland recently. He spoke to the city club and I had the chance to chat with him and hear more about the organization. Certainly I’ve been aware of that for several years because they operate a fellowship program here in Portland and as well as many other cities.

Ben Forstag:

I think it’s really interesting and this is a great service because it’s a huge need for a lot of professionals out there. I know my father, for example, he’s in his 60s, he’s had 2 careers now, one in sales, one in computer sciences, and he’s looking for the next step in his life. He wants to do something different and something that benefits the community. He’s got special challenges because he just moved to Portland, for example, and lost the professional network that he had back in Ohio. Encore.org helps folks like that get connected into the social service community. The organization offers a lot of resources for people looking for encore careers, including a blog with stories from professionals who have made that transition into their second social-good career, white papers on the many benefits of pairing older professionals with social service organizations.

The benefits here being both for the organizations, the workers, and society as a whole. I should also mention they also sell a book called The Encore Career Handbook on how to find what makes a difference and what will pay the bills for you. I admit, I’ve not read this book and I’m not quite the target audience, I’m a little too young for that, but it has great reviews on Amazon and it looks like a really solid resource.

Mac Prichard:

In fact, Ben, we’ve reviewed that book on the Mac’s List blog. Laura Schlafly, who’s also a contributor to our book, did a terrific review of the book back several years ago and spoke very highly of it.

Ben Forstag:

What we’ve learned today is that you’ve never been in my office and I’ve never been to the bottom of the Mac’s List blog archives. Good stuff.

Encore coordinates a network of national and local organizations and programs dedicated to engaging older workers in the social-good sector. If you’re interested in an encore career you should definitely look through the organizations in their network, as these would be hot leads for work and networking opportunities. The coolest thing, I think, about Encore, and this is something Mac just mentioned a few minutes ago, is their fellowship program which directly pairs talented older professionals with non-profits and public agencies. The program works like a paid internship for more seasoned workers offering high-impact, flexible, time-limited paid assignments. Man organizations around the country host Encore fellows. Here in Portland, for example, I know social venture partners participates in the program.

Cecilia Bianco:

Yeah. They actually just reposted their Encore fellowships and they’re starting again for the next term.

Ben Forstag:

Yeah, and those are posted on macslist.org.

Cecilia Bianco:

They will be.

Mac Prichard:

For our listeners around the country, the fellowships are offered in many other cities besides Portland, so we encourage you if this does interest you, and it’s not just in Portland but around the world, to get on Google and check it out.

Ben Forstag:

Yeah. Last time I checked it was 2 dozen different cities had some version of this program and they’re always adding more cities in. The fellowship program, I’ll say, is pretty competitive. They only take about 250 fellows at any one time, but it’s a really fantastic way to learn firsthand about non-profits, foundations, and other social institutions, to establish contacts and personal networks in a new sector, and to make a real good contribution using the skills, experience, and knowledge you may already have from your first career. Check it out. Again, the organization, their website are encore.org. As always, we’ll include links for these sources in the show notes.

Mac Prichard:

Well, thank you, Ben. Do you have a book or website or perhaps a podcast episode that has been helpful to you in your job search? Please let us know and write Ben directly and he may share your suggestion on a future show. Ben’s email address is info@macslist.org. Now, let’s turn to you, our listeners. Cecilia, I know our mail bag takes many forms. Sometimes it’s a Facebook message, sometimes you get a tweet, sometimes you even get an old fashioned snail mail message from readers. What do you hear from our listeners this week?

Cecilia Bianco:

This week I got an email and a reader asked, “What advice do you have for working professionals who would like to shift careers to a new field?” We talked to many people who are interested in a career shift. Mostly who want to move into the non-profit sector, but the advice we always give can apply to pretty much any field. If you want to shift careers to an entirely different field, the first thing to do is research what employers in that field are looking for when they’re hiring. By research I don’t just mean going online to find answers, I mean getting out and networking in that field to meet people who can directly tell you what employers want.

Going to the right events where you’ll meet professionals in the sector you want to work in and reaching out to those professionals for advice, and also to build lasting connections with them. Joining professional groups or industry groups in your local area is a great way to meet more people and find out about the relevant events you should be attending. It can also be good to target 2 or 3 organizations that you’re interested in working for and ask for informational interviews with people who work there.

Ben Forstag:

I’ll just add, if you’re looking for some tips on finding, organizing, and conducting informational interviews, check out the Mac’s List blog. We have lots and lots of resources there to help you with that.

Cecilia Bianco:

Yeah. We definitely do. We also have some really good content around how you can realize and leverage your transferable skills when you’re making a career transition. Once you’ve done your research and figured out what skills and experiences you need to get hired in this new field, you can make a plan for how you’re going to do that. A great way to get the experience that you need, especially if you’re not ready to quit your job is to find volunteer opportunities or work on the side that will help you build up your background in the new field. This way when you’re ready to start applying for jobs, you’ll have a better chance of getting them. It’s also an opportunity to meet more people in that sector and potentially get recommendations from them or use them as professional references. Mac and Ben, have either of you switched fields completely during your career?

Ben Forstag:

My career’s a little too young to have had too many stages in it, so I’m still in my first career. At one point I imagine I’ll transition to doing something else or having my encore career. I think the tips you put out here were really good for when that time comes.

Mac Prichard:

I’ve switched careers several times, Cecilia. My first career was working in DC and Boston with human rights organizations. I wanted to change to state and local politics and government. The way I did that was using the very techniques and methods that you described, the informational interviews, figuring out what employers were looking for and getting clear about my goals, and sharing and showing my strengths. That made me an attractive candidate and help me make that switch.

Cecilia Bianco:

Yeah. We definitely talked to a lot of people today, especially in our local area that are using networking and informational interviews to make that switch. It seems to be the easiest way to get going when you’re transitioning.

Ben Forstag:

I’ll add here that I don’t think you switch careers, you don’t turn on a dime. It takes time to make that pivot. I think the best strategy is to start the networking, start the research phase before you’re done with career number one, so that when you’re ready to make that jump that you’ve already created that base of support and that foundation for making the transition.

Mac Prichard:

Good advice. Thank you, Cecilia. If you have a question for us, please email us. You can reach us at communitymanger@macslist.org. These segment by Ben and Cecilia are sponsored by the 2016 edition of Land Your Dream Job in Portland and Beyond. We’ve made the complete Mac’s List guide even better by adding new content and making the book available on multiple e-reader platforms. We’re very excited about our new edition of the book, Land Your Dream Job in Portland and Beyond, that we published on February 1st. For the first time now you can read the book on your Kindle, your Nook, or your iPad. You can also order a paperback edition. Whatever the format, our goal is the same. We want to give you the tools and tips you need to get meaningful work. For more information, visit macslist.org/ebook and sign up for our ebook newsletter. We’ll send you publication updates, share exclusive book content, and give you special prices.

Now let’s turn to this week’s guest expert, Michelle Hynes. Michelle Hynes is a certified coach who helps people navigate planned and unplanned transitions at work. Her clients are people who care deeply about how their work serves the world around them and want to grow their impact with integrity and ease. Before moving to Portland from Washington DC, Michelle spent more than 20 years in the non-profit sector as a program director, a board member, and a volunteer. Michelle, thanks for coming to the Mac’s List studio.

Michelle Hynes:

Thanks so much for having me.

Mac Prichard:

It’s a pleasure to have you here. We’re talking this week, Michelle, about changing careers. I think when people hear this topic they think about, frankly, people like me in their 50s who are baby boomers. This isn’t just about baby boomers, is it?

Michelle Hynes:

I think it’s about all of us now. I’m 47, so I’m a little too young to be a boomer, and I would say I’ve already reinvented my career at least twice. Once by necessity and once by choice. For me, my most recent career shift involved going back to school. I think that those kinds of changes and what that next change is going to be is going to become more common for all of us at all stages of our lives.

Mac Prichard:

A lot of our listeners are millennials, people in their 20s and a early and mid 30s, is this something they should be thinking about?

Michelle Hynes:

I think that because all of us are living longer we’ve got this huge longevity dividend, as Stanford University’s Laura Carstensen would call it. We’re all millennials and those of us who are a little older and a little younger, we’re going to have the chance to invent and reinvent our career story over and over probably into our 70s. It’s great to have the opportunity to think about it early and often.

Mac Prichard:

Because of longevity, which is a good problem to having, I think, we all, whatever our age group, should be thinking about changing careers. Aside from that, what are some of the other reasons why people think about changing careers?

Michelle Hynes:

I think for those of us who are fortunate, we get to change careers when we want to spend our work lives doing something that we especially care about. People may start doing something as a volunteer and want to spend more of their time and energy doing that. People may find themselves in an industry that’s changed and they want to change sectors or roles within that industry or shift out of that industry. For example, if you’ve worked in health care for a long time. That’s an industry that’s changed hugely. If you work in technology, that’s an industry that’s really changing. If you work right now in oil and gas, let’s say.

There are a lot of reasons that people might change careers both in terms of their professional interests and how they want to spend their days. Also, particularly for those of us in mid life and older, we might need a different kind of work-life balance, or we might want a different kind of work-life balance. We might be caring for grandchildren, we might be caring for our parents, and so I think there are different personal and professional reasons that people seek that change.

Mac Prichard:

It could be because people want a more purpose-driven job.

Michelle Hynes:

Absolutely.

Mac Prichard:

It could be because of life events like starting a family or caring for an aging parent or other family member, or it could be because we simply have no choice. We’re being laid off and the opportunities in our current profession just aren’t there.

Michelle Hynes:

Right. I think, changing context, both personally and professionally I know that you’re recommending in this episode encore.org and the Encore careers handbook. A lot of folks in their 50s and 60s, people who are boomers and beyond, are taking the opportunity to shape their own encore, to leave a legacy with their work in a particular way.

Mac Prichard:

Whatever your age group over whatever point you might be in your career, what are questions that people need to address when they start thinking about switching careers?

Michelle Hynes:

Two big kinds of questions. One is what’s the change you want? What’s the nature of that change? Are you trying to shift fields, shift sectors, shift the kind of job that you’re in? How much opportunity do you have to make your own choices in that circumstance? You mentioned being laid off, which is a different circumstance than, let’s say, working at Intel for 20 years and having the opportunity to do an encore fellowship, for example, which is one of the things that people can do here in Portland. Then I think looking at the nature of the change and then also really thinking about what is the work that I want to do next? Looking at both the change and the career aspect of that question.

Mac Prichard:

As with any career transition, people need to do their homework. What are some specific tasks that you encourage people to do as they think through those steps that you just outlined?

Michelle Hynes:

I think to really be an explorer of yourself and explorer of the environment, walking through your day noticing what are the things that I really love to do? What are the things that I’m doing whether they’re work, whether they’re at home, whether they’re in my volunteer life or in my faith community? What are the things that I really enjoy and what’s that telling me about myself and the next step that I want to take? I think that’s one really good thing to do is just that purposeful and consistent self-reflection. I think talking to people who know you well and talking to some people who don’t, having conversations with people who are family and friends about what you want to do next and why you’re looking for a change. Then also more formal informational interviews using the network you have and expanding that network in order to take a series of steps along a path toward where you want to end up.

Mac Prichard:

That first step that you were describing, it’s also like something many of us have seen happen in the workplace, which is what’s called a 360 review where you ask your colleagues about your strengths and candidly your weaknesses. You get that candid feedback that you can use to make changes.

Michelle Hynes:

Yes. That’s a great analogy.

Mac Prichard:

Yeah. Good. Then you talked about informational interviews. We’re big fans of informational interviews at Mac’s List. Is there a particular way you would have people prepare for those conversations, people who are planning a career change? Often people say to me, “I’m not sure this is working,” when they go out on an informational interview. If you were helping someone prepare for a conversation like that what would success look like at the end of a 20- or 30-minute conversation they might have?

Michelle Hynes:

One of the reasons that I recommend starting with the self-reflection and the family and friends is that it gives you an opportunity to try out some different versions of the 1 or 2 sentences that you want to be able to say when you enter a more formal informational interview. You want to be able to say something like, “I’ve had a great career at X organization for the last 20 years and what I’m really looking to do now is to take my strong set of technology skills and apply that to a small- to medium-sized non-profit organization that wants to use technology differently to meet their mission.” To get really crisp and clear about where you’ve been, where you want to go, and what’s bringing you to that next step. I think it’s important to have that 1 or 2 sentences.

I think it’s also important, and you’ve written actually a great blog about this, what can you give? When you’re sitting down with someone in a 20- to 30-minute conversation, what’s the value exchange? What can you offer in that conversation that might help that person who you may be meeting for the first time and what is it that they can do to help you have the next conversation, meet the next right person, learn something that you might benefit from in terms of what you are looking to do?

Mac Prichard:

Yeah. I have to give credit to Nathan Perez, who’s the author of the 20-Minute Networking Meeting, who lays out a structure for how to have conversations like this. One of the suggestions he has is at the end of the conversation say to someone, “What can I do for you? How can I help you?” What I love about that is it just recognizes that when you’re going into those conversations you have so much to offer. It just puts you on equal footing. It becomes a peer-to-peer conversation.

Michelle Hynes:

Yes. I think that’s another really important point. That is maybe more true of people in mid life than those of us who are earlier in our careers is to remember that even though you’re potentially entering something that’s very new to you, you are bringing a lot of experience, a very rich set of networks, and a lot of capacity to build bridges between what you’ve done before and what you might do next. When you’re sitting in that 20-minute conversation, even though you’re asking for something which can feel uncomfortable, you also do have a lot to give.

Mac Prichard:

People need to get good feedback from peers and friends and family about their strengths and challenges they need to get out and do informational interviews where they share their goals, get insights into opportunities in the field they want to crack. What about retraining? Should people be getting certification or earning graduate degrees? How important is education in the career switching process?

Michelle Hynes:

I think it can be really important in a number of ways. One of the things that any new education, a course, a certification, even an informal set of networks that you can put on your resume, it shows that you’re a continuous learner, which is super important for everybody in today’s work environment and I think especially important as we get older. We can sometimes sit in interviews and think, “Oh, I wonder if this person will think I’m too old or not know the right technology. First of all you’re just demonstrating that you’re a learner. Secondly, you genuinely may need to learn new things. All of us do because the world is changing so fast and depending on the industry, certifications can be important because there’s a certain kind of specialization.

Mac Prichard:

Let’s talk about the challenges people will face as they switch careers. What are some of the barriers they should anticipate finding and how might they address them?

Michelle Hynes:

I think the first thing to recognize is that it’s going to take time. Even if you might take a couple small jumps along the way to where you want to end up, it’s important to let the process take the time that it will take for you to end up where you want to go. It can be uncomfortable to be in a situation that is new when you haven’t been in school for a long time or you haven’t been the new person at work for a long time. Just to recognize that there is an emotional and a psychological component to making a change in your work environment, in your field, in your sector. In yoga or meditation, this is something that we call beginner’s mind.

It’s really important to enter this shift balancing the idea of beginner’s mind and it’s going to feel new and I’m going to learn. I’m very experienced and I have a lot to give. Just being able to hold those 2 things at once I think can help people because it’s a little more like a chess game than a checkers game. Sometimes it’s not a straight line, it’s a couple steps this way and a couple steps that way. Just as I said earlier, really being an explorer of this new territory.

Mac Prichard:

Okay, so be prepared for uncertainty.

Michelle Hynes:

Be prepared for uncertainty.

Mac Prichard:

Well, we need to start wrapping up, Michelle. Are other points you’d like to make about switching careers?

Michelle Hynes:

More often than not, everyone around you wants to help. Use your network to not be afraid to expand it in some of the ways that we’ve talked about here and I know that you’ve talked about on other shows. Keep a spirit of both humility and generosity throughout the process, and to have fun. However it shows up, your career change is an opportunity.

Mac Prichard:

Well, thank you, Michelle. Now let’s talk about you for a moment. What’s coming up for you next? What are some new projects that you have on the horizon?

Michelle Hynes:

I’m very fortunate to be working on encore.org’s national conference that’s coming up in just a couple weeks. If folks are visiting the encore.org website, check out all the great speakers. I also am looking forward to continuing to coach non-profit leaders and people in a couple different sectors. That’s a pretty fun part of my 2016 and looking forward to continuing to explore Portland, which is my relatively new home.

Mac Prichard:

Thanks for joining us and we’ll be sure to put links to the encore.org conference in the show notes that go out every Wednesday morning. Our listeners can find Michelle online at michellehynes.com. Is there anywhere else people should look for you online, Michelle?

Michelle Hynes:

Nope. That’s the place to find me.

Mac Prichard:

All right.

Michelle Hynes:

Thanks.

Mac Prichard:

Thank you for joining us. We’re back in the Mac’s List studio with Ben and Cecilia. What were your most important takeaways?

Cecilia Bianco:

I thought she had some really great tips, but my main takeaway is how positive her mindset was about it and that other people should have the same mindset that any career change is an exciting new venture. If you look at it like that it’s a lot less scary and it takes a lot of the negative out of it.

Ben Forstag:

I liked a quote she said and I wrote it down. It’s, “Let the process take the time it’s going to take.” I think that’s so important because I know we’ve all been in periods of unemployment and there comes a point where you start to panic and you’re trying to find another job right away and you can’t force it, and you can’t speed up that period of unemployment sometimes. It’s just going to be the time it’s going to take. For me it was 4 months. That was the time it took to find a good, meaningful job and top try to cram everything I needed to do to find that job into 1 month was never going to happen. Just giving some space to yourself and taking it a little bit easy on yourself knowing that it’s just going to take some time.

Mac Prichard:

Yeah. It is a process, but there are models out there that you can copy and you can learn and you can apply to your own career. The most important point I heard her make was that whatever your age group, this is something we all have to be prepared for because we’ll all look at it at different points in our career, whether we’re millennials or members of generation X or baby boomers. There are models that we could use to figure out how to make that switch and whatever the reason why we might want to do it. Whether it’s to find a purpose-driven job or because suddenly we’ve been laid off, but we have tools.

Well, thank you for listening. We’ll be back next week with more tools and tips you can use to find your dream job. In the meantime, visit us at macslist.org. If you like what you hear on the show you can help us by leaving a review and a rating at iTunes. This helps others discover our show and Ben and I actually have examples of recent reviews that we’d like to share with you. Ben?

Ben Forstag:

This one comes from Brighton West, who is a hiring manager. Here’s what he or she wrote, “As a hiring manager, I can vouch for the validity of Mac’s podcast. Networking is so important and doing it the right way is even more important. I love doing informational interviews. About half my hires have gone through info interviews prior to being hired. I really prefer to not do an open cattle call. I’d much rather identify potential candidates in advance.”

Mac Prichard:

Well, thank you Brighton, and thank you Ben for reading that. I have a review from Mark [Mescotto 00:28:35] who writes, “Really liking this podcast, which is full of great inside tips on how to find the perfect job. I just left my job and I’ve already learned about informational interviews, creating a LinkedIn page, resumes, and more. I appreciate the different guests who come on every week. That’s a nice feature and I’m looking forward to continuing to listen to future episodes.” Thank you, Mark, for leaving that review. We hope that you’ll consider leaving a review as well because that helps push us up in the iTunes rankings and that helps us reach more listeners, thereby help more job seekers. Thanks for listening.