Are you feeling stuck in your career but not ready to retire — and definitely not ready to start from scratch? In this episode of The Retirement Success in Maine Podcast, Ben and Curtis sit down with career strategist Mike Dwyer, founder of Emplana Career, to reveal how professionals in their 50s, 60s, and beyond can pivot into their next chapter without losing all the progress they’ve already built.
Mike brings decades of experience from the private and public sectors, and he shares how to outsmart today’s job-market challenges, beat the bots and AI that screen résumés, and use his proven five-day Emplana Career Framework to uncover new opportunities fast. From networking that actually works, to building a personal “career board,” to breaking into leadership roles or mission-driven organizations later in life, Mike gives listeners a playbook for creating meaningful, energizing work in the second half of life.
If you’ve ever wondered, “What’s next for me?”, this episode delivers the clarity, confidence, and inspiration to take your next step — without starting over.
Intro & Guest Background – Setting the stage and meeting Mike Dwyer of Emplana Career. [00:01–02:50]
Why Career Pivots Feel Hard – Mike’s journey, the résumé story, and why professionals feel stuck. [02:50–09:05]
Today’s Job Market Realities – AI, bots, applications disappearing, and how to fight back. [09:05–14:47]
Networking & Connection – Getting in the right rooms, networking for introverts, and building real relationships. [14:47–24:59]
The Emplana Career Framework – Mike’s 5-day workbook and how to explore roles without starting over. [19:16–28:32]
Leadership, Culture & Mentorship – Moving into management, evaluating culture, and finding helpful mentors. [28:32–45:18]
Energy from Innovation Ecosystems – How startups and mission-driven orgs unlock opportunities later in life. [49:51–53:10]
Resources:
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Intro (00:01):
Do you struggle with what it means to be successful in your retirement? Trust us, you're not alone. Welcome to the Retirement Success in Maine podcast. Here you'll go in depth with guidance point advisors, investment consultants, to hear stories about how retirees in Maine are navigating a successful retirement. Get insight into the inevitable challenges of aging and define what a successful retirement looks like.
Ben Smith (00:26):
Do you ever feel stuck in your job but dread the idea of starting over? Maybe you've built a long successful career, decades of experience, deep expertise, but maybe shifting technology, corporate shakeups or plain old burnout are making you ask what's next? And more importantly, how do I make a change without going back to the beginning? Be hoy there. Listeners, welcome back to the Retirement Success and main podcast where we explore how to live well, plan smart, and find deeper meaning in retirement. I'm Ben Smith and joining me as always is the LinkedIn to my resume, the networking event to my business card, my co-host and coworker Curtis Worcester. How you doing today, Curtis?
Curtis Worcester (01:04):
I'm doing well, Ben. I'm doing well. I like this certainly on theme with today and just definitely had my fair share of awkward networking events, but we got to do what we got to do to make connections in life, right?
Ben Smith (01:17):
That's right, yeah. And we've both done enough chamber events and business after hours.
Curtis Worcester (01:22):
That's right.
Ben Smith (01:23):
You got to have the sticker on yourself and get out there and just start talking. But obviously, speaking of connections, today's guest is someone who has built a career helping others reconnect with their purpose and professional path, especially when they're wondering what now.
Curtis Worcester (01:39):
Yeah, that's right. And like all of our shows, Ben, we love to bring in a guest, an expert. So today's guest, Mike Dwyer, he's the founder of Emplana Career. So after a long career spanning both the private and public sectors, including consulting roles at Ernst and Young and Deloitte Consulting and earning a master's in management from Salve Regina University, Mike, our guest launched Emplana with a mission to help others figure out their next chapter. So Emplana career based in the Cambridge Innovation Center in Boston, Massachusetts supports professionals often in tech, finance, accounting, and law as they seek clarity and direction in their next career move. So Mike is also the author of the Emplana Career Workbook and Toolkit, a five day guided program to help people quickly gain confidence, structure and opportunity. So whether you're looking to pivot, downshift, or re-engage in a new way, our guest Mike brings the tools to help. So with that, please join us in welcoming Mike Dwyer to the Retirement Success in Maine podcast. Mike, thank you so much for coming on our show
Ben Smith (02:50):
Today.
Mike Dwyer (02:50):
I'm delighted. Thank you for having me.
Ben Smith (02:52):
Well, Mike, obviously we have a lot we want to talk to today and obviously in terms of career pieces like that, but we also want to make sure that our audience gets to know you a little bit. So love to hear your journey. You've worked in some pretty high powered environments, big four firms, public sector roles, startups. What inspired you to focus your second act on helping others navigate their own career transitions?
Mike Dwyer (03:18):
I think I saw that collaboration is absolutely necessary, and if we have time later, I'll talk to you about some paid focus groups I commissioned and additional learnings. But just to be really clear, the Emplana career is the DBA name. You folks are financial professionals enough to know doing business. As you know that the underlying LLC name is career collaboration now nerd that I am, there's no marketing skill there and even I couldn't spell it reliably, so we moved on to a career. But I think what happens after you have a long career is you realize, call it a personal board, call it me, call it you folks, convene, reflect, dive in. And obviously the more you work in this, you start to have some frameworks and other things. But the essence of what motivates me and the people around me is to foster collaboration that's really customized to where the person is and helping them see what a range of possibilities from very safe to quite ambitious.
Curtis Worcester (04:30):
I love that. I love that. And Mike, we read one of your first career coaching experiences was actually helping a friend with his resume, and that snowballed into a whole new career. So can you just kind of share that moment when you realized that this was truly something that you were uniquely good at?
Mike Dwyer (04:48):
Well, thank you. Or at least had something to say. Curtis and Ben, I'm sure already in your careers people will come to you and say, take a look at my resume. Absolutely. Right. And what's the norm? You emphasize this, you say, oh, wait a minute, this is out of sequence. It doesn't make sense or whatever. You might, if you know the person, you might say, this is you're underselling yourself. If you know the person well, you might tune it up and say, this is a little brash, whatever, but one fine time 15 years ago, I'm looking at a resume and who knows why? Maybe because I knew the person, some new things happened. The first one was that this was sort of a good strong middle manager in financial, in banking, and I found myself saying, huh, should this person do a stretch for an executive role before they retire? I mean, it looked like they had another five to seven years when I was working with them.
(05:43):
Gotcha.
(05:43):
Should they stretch? On the other hand, it is a joy in life to be really good. I mean, another alternative for that person would've been to consolidate as a line professional. Somebody with a 35 year career could be one heck of an analyst or a solid white collar contributor. And so I guess the first thing to answer your question, the first thing I found myself is I was playing 3D chess that time instead of just one game
(06:09):
Board.
(06:10):
And the second thing is, and this is something I've started to say a little too much maybe, but when you look at a couple of new tiles, a couple of new skills, what would you do to change the mosaic? What would be one or two things that would suddenly move you into something that's more in demand closer to your authentic self, TBD? But I hope already in these very few minutes, you can already hear that these are always custom suits,
(06:38):
Men, women, whatever. It's always a situational ethic. What have you done? What's comfort for you? Stretch. So that's really kind of what went on. And then of course, being a nerd from Ernst and Young and Deloitte, what do you do? You build a framework. How would I know how to help somebody do some assessment or how to organize, et cetera. But that was the kickoff is for whatever reason, looking at that resume that time changed how I look at resumes and I'm always trying to spread this contagion. So I'm hoping that the next time you look at some resumes, you'll be saying to yourself, huh, what would it look like if this, and all the rest of that. Sure.
Ben Smith (07:19):
Yeah. Gotcha. Well, you just brought up some of your consulting experience, and of course you've had careers both inside the machine and outside as a consultant. Right. So can you just talk about obviously seeing both sides of that, of the business and the organizational piece, how have those experiences informed the way that you coach your clients through major changes?
Mike Dwyer (07:41):
Well, one thing I'd like to bring up is that a lot of the work that I'm lucky enough to be able to do with people developing thoughtware whatever, is really reflection research. I think that the direct answer to the question is how to think about how many seats at the table you've had. So have you been the person? A great example, you're probably familiar with request for proposals, right? Especially absolutely. We got to get the yellow lines painted on the parking lot or we got to get a new system. Well, you know what? You might be somebody who's done a hundred engineering RFPs in the public sector, or you might've been a service provider who answered them. And so the more of those roles you've played, whatever your domain is, whatever you're trying to do, you want to really be thoughtful. And this is again, where you need some help.
(08:34):
You need collaboration, a personal board to really walk through. Okay, what if you were King Kong at this thing? If you had had every seat at the table, what would that look like? And do you know where that leads you? There's some interesting implications there. You might have a job that you can get an 8% raise doing the same thing you're doing today, but you might find a job that's basically lateral, same pay, whatever, but it lets you take a different seat at that table, one of the different roles that might be a better strategic chip to put on the poker table.
Curtis Worcester (09:05):
Gotcha. I like that. That's a great example. So this is great, right? We're getting right into kind of what we really want to discuss today in this idea of changing our work role without starting over. And I know for a lot of the people that Ben and I work with every day and our listeners, we're thinking kind of people in their fifties or early sixties here, there's maybe a fear that pivoting to something new means they're throwing away everything that they've built. So just kind of foundational as we get into this topic for you, Mike, why do so many people feel stuck between retire now or start at the bottom again? Why is there no middle there?
Mike Dwyer (09:46):
Well, I think Curtis and Ben that unless the natural thing is to think you're going to do it the same way the next time, and if you do that, then yeah, you do need another 40 years. But what do you say we cheat. What do you say? We consider One of the things that's happening right now in a tough labor market is I refer to, in my own mind, a job to me is it's actually a monolithic thing. It's got a lot of bits in it, but it's a whole carved out thing that has a title. One of the interesting things that you can help people in starting over moving laterally and then up is if you look at, okay, I call it monolith. Another thing you could call it is a molecule. If you look at the atoms and say, these are elements of this job that I've done a lot, and I could bring those elsewhere or I could put those on a freelance platform. Now we're talking.
Curtis Worcester (10:38):
Yeah,
Ben Smith (10:39):
Yeah, that's great. Gotcha. Well, you just mentioned something, Mike, in terms of obviously the job market, and I know right now we're recording, we are still in the middle of a government shutdown federally. We are still seeing companies with being pretty big layoffs. They're announcing really great earnings, but they're also announcing that maybe to keep those earnings going in the future that they have to shrink their workforce quite a bit. Though we hear this frustration a lot, whether it's now or in other cycles that I've applied to dozens of jobs online and I never hear anything back that the resume black hole is real, and especially in a day and age where with AI and we got screening tools, that's probably helping HR do their jobs a little bit better. What's your advice for fighting back against the applicant tracking systems that are out there and getting noticed?
Mike Dwyer (11:33):
Well, because of your financial acumen, I can throw words around like portfolio duration. A lot of this stuff has to be, it can't be single track. So let's talk a minute about the bot war. When you go to the MIT thing and six different universities are seeing which robot can push the other one over, that's fun, but what's going on here is not fun. And if you really want to deepen the bitterness, employers are quoted in the press now as being angry that candidates applicants are using AI to embellish. So we have a complete robot war going on, and a friend sent me an article to this end and it turns out that yeah, what you do is you put some stuff in a white font that a human reader can't see, but that the bot does and so on and so on and so on.
(12:26):
Here's how, what I would suggest is how to play the portfolio. First of all, if you are going to do anything in the classic cover letter and resume, you got to do some research. I think I've mentioned to you that I work with a local career office, job shadowing, mentoring. So I have the luxury of watching a series of really sharp MBAs come by and the like. And if they're reporting, I got six versions of my cover letter with all the right keywords and I'm only getting a couple of nibbles, let's not spend a ton of time at that. So what do you do on that front? I look for a concept I call the cover letter has to write itself. I have to look at your firm, get a read of Ben and Curtis's resume client. I got to be so excited that off the cover letter comes, I got to be there and look what I have. So what I'm saying is that if you do want to break that mold, the way to do it is to find something that's so interesting, a good match that you do want to put that in play.
(13:28):
But I don't think that's the only thing you want to do. I'm big on, as you know, Steve Dubin and I are very big, the person who introduced us very big on networking. I actually have a professional networking seminar registered with the commonwealth of mass, blah, blah, blah. Steve has run commercial networks. So I think in today's world that you really want to use every opportunity you can, and I've mentioned to you before how important intentionality is.
(13:53):
So I think what we want to do, we want to look now and say, what's a couple of networking things I could do a month? How do I get out there? How do I look at eyeballs? How do I go to the place that has a meetup about what I'm interested in and say, Hey, I'm interested. Could you tell me what's emerging? Can you shine some light? So now what's happening is you're nowhere near bots, you're near people. And the more of that, so one of the things I have, this new thing I've been talking about is topical networking. And this is the last thing I'll say because I'm going a little long here. I know.
(14:28):
No,
(14:29):
No, it's okay. All right. Well, topical networking means if I have a choice of taking a good course online at LinkedIn or as my colleague Steve Dubin says, driving 60 miles for a meetup, or I can talk to people who do it and learn that way. Guess which one makes sense in this climate?
Ben Smith (14:47):
Mike, I want to add something there too. So I have a C charter. So the charter financial analysts, it's a pretty intensive investment designation. We have local colleges, universities, and they always go, well, they come to me and I'll do a little mentoring and they'll say, well, how do I get a job in this industry and how do I meet more people like you? Ben? And I always told 'em, it's like, geez, the c FFA Society in Maine, yes, they mostly meet in Portland, but you can go and it's at $10 I think to join as a non-member, a luncheon session. They have luncheon sessions. I think every month it's like pay $10, go to Portland and sit with a room of 35 to 40 decision makers that are that designation. And you get a lunch and you get to learn something and you're going to sit at table with all of them.
(15:42):
And by the way, you're going to be the only younger person in that room and they're going to go, where'd you come from? And they're going to want to know all about you. It's like to your point about networking is like people just won't take that extra step a lot. That is what I'm seeing on maybe the university side. And you go the ones that do, all of a sudden everybody, it's a feeding frenzy over them because they go, that's the person I want to have at my company. The one that would take the extra is excited about it, motivated they want to be in this industry. Those are the sorts of people. So I know it's an aside story, but I wanted to share the networking piece of, to your point about getting focal and getting where the people are going to be that are decision makers. And then once you figure that out is going, the cost of entry is $10 and maybe a trip to Portland and maybe you do a run at Trader Joe's while you're down there, whatever you want to do, not a big deal, just go show up at a lunch and you'll meet enough people that you'll get so many follow up conversations and calls and zooms. It's well worthwhile.
Mike Dwyer (16:47):
Now you've got me going.
(16:50):
That's a phenomenal example. So lemme tell you about joining the IEE. Okay, I'm a nerd, but maybe you're a marketing person. We've got the same story for you. So it costs me, I think it's $175 a year to become an associate member of the IEE electrical engineers. I don't know anything about electrical engineering, but I'm happy to pay my dues and make a small donation to their foundation. So let me tell you about two seminars. One that I attended and one that I wasn't able to, but it is so apropos. It's exactly like you say. The first one was on robotics actually it was a two day event and it was short money and the first they introduced you to cloud computing. Now this is not a vendor white paper, this is electrical engineers telling you what's going on. They took was robotics. What they did is they brought people from the University of Lowell, their robotics and a local company and they let us play with military robots.
(17:45):
So one, two man carry robot can pick up IEDs and take 'em safely away. The other one is a one man carry 30 pounder with an extendable tail that you can toss into a building and it'll even go up the flight of stairs and the camera will look around and make sure it's safe for the soldiers. Now, do you have any idea how much that gets your juices flowing and you're talking to companies and you can ask questions like, I'm a young person, what do you need an intern? I'm an older person. You know what? At that exciting company, you still need procurement, you still need hr. And let me tell you about the other seminar I was unable to attend again two days. Day one is we're going to teach you how to build your own drone. Oh, you don't have to buy one. We're electrical engineers. We're going to bring you parts. And just like being a little kid at camp, after you do the meeting, you're going to have a pothole or something. No, you're going to have a drone. Nice. Day two, I'm going to teach you about FA regs. Now it turns out there's some really interesting little sideline businesses with drones, but you got me all excited by talking about the CFAs. And I think what we're saying to you listeners is look what happens when you get serious.
(19:04):
Look
(19:04):
What happens when you say, what am I truly interested? What would I be willing to go pursue? I think we can all imagine some really good things coming out of any of the settings we just described.
Curtis Worcester (19:16):
Yeah, fantastic. Mike, I do want to keep going here and I'm going to shift it back towards you a little bit In your work. I want to talk about the Emplana career workbook and toolkit, right? It's your five day system. So for somebody who maybe feels overwhelmed by the idea of changing careers really at any point, but again thinking later career maybe in changing what makes your approach doable and different for people.
Mike Dwyer (19:41):
Well thanks. I think it's pretty simple. And so that's why what I want to do is I suggest five days, but I don't care if it's five hours or five weeks,
(19:50):
It's
(19:51):
Just a handy thing to break it up. I have in front of me a little chart from that workbook and here's the verbs, the five verbs that I'm suggesting from Monday to Friday. Review, assess, collect, sort, and choose. So what I want to see happen is that somebody and the reason to break it into time boxes, if we say in the consulting, we all know professional services on this call, you don't want to go down any rabbit holes. And so what are you meant to do? As my British friends would say, what are you meant to do on Monday? You're supposed to look through some old files, contacts, email, you're looking for things that you've done, people you want to follow up with, ideas, companies, sectors that intrigued you, you're harvesting your past and it doesn't need to be perfect. Like any process when you go back and look at it, some will be nuggets that you want to do more with and some of, well that's interesting.
(20:47):
That's nice to have. Excuse me. And then I think what you want to do is you want to start moving towards the present and say, what am I involved with now? Am I doing? And then your concept, I have a thing I call career budget. You want to start saying, alright, what's my little time pie chart for this stuff? Am I doing some networking? Do I set aside some time for skills development? So by the second day, you're taking a snapshot of the influences, the books, the authors you follow, and now you can, I hope you starting to see where this goes. Alright, so I'm going to start to collect this stuff together that says, well does this look like a different role in the same sector or is this starting to show me things that I could take elsewhere? And this is probably the point where I just have to stop and talk about community personal board and all this bit because thank you. This is not where to go at alone. If there's anything, do we have time to talk about focus groups for one minute about
(21:52):
Yeah, yeah, definitely.
(21:54):
Alright, so I commissioned out of my own Mike Dwyer dollars here, some marketing strategists to do some informal focus groups around what do people think about career and coaching and how do we go about it? The age cohort was more in the 25 to 40, but what was the result was striking after some conversations that moved around the landscape, it netted out to be this, well, if I'm going to get in shape, you know how you join the gym on January 1st, I'll hire a trainer, but for the career I should be able to figure it out myself. I don't buy it, I object strongly. You need help. And I love the idea of a personal board when I see it in the press, in the business press, but I think it's too passive. I think you need to convene them. So let's say it's Ben and Curtis. I'm going to count on Ben. He worked with me before. I'm going to count on Curtis, he's my cousin. He doesn't even know what I do for a living, but he'll tell me if this sounds timid or if it's way too brash. We need people to help us brainstorm. And this ties back, remember the underlying name is career collaboration.
(23:01):
I hope you're seeing where this is going now by midweek, you're starting to touch base with some others, whether it's five hours in or five weeks in, you're starting or five days you're starting to check with some others. And that is where you begin to think where you're drawing out, am I just going to follow one track? I'm in a good sector, I know what I'm doing, there's plenty of employment here, but I'm going to start thinking about another role or a bigger role or what skills I need or are we going to, again going to your portfolio? No, when interest rates were what 0.1%, I didn't really want to hold a lot of bonds. So this might be time where you start talking about freelance. Now again, nerd that I am, it turns out that guess what percentage of people on the Upwork freelance platform are boomers? Go ahead and take a guess
Ben Smith (23:55):
Quarter.
Mike Dwyer (23:56):
Oh, that's generous. No, it's 9%.
Ben Smith (23:59):
But
Mike Dwyer (23:59):
What the answer tells us is that it ain't lonely. You're not a majority, but you have no reason to stay your hand. Then another nerd data point is that when I look at Fiverr, there are something in the order of 700 skills. I mean at the very top, they call it professional career and creative, excuse me, creative like administrative or something. They got these giant buckets and then when you drop down to them, you start getting into another layer and so on. And then you get down to just incredibly specific skills offering. And I think we're helping your listeners when in this down job market we're saying to them, well after this harvesting, after this midweek meeting with your personal board, you're starting to have this little sense of adventure and shopping that, and I think it's incredibly mentally healthy to be taking steps on your own behalf, not just, oh my God, this is awful.
(24:59):
But saying, alright, what would be something I could try and bringing that I tell people in the networking seminar, never do a big ask Curtis, get me a job. Maybe for your brother even then that might be pushing it. Sure, yeah. But Curtis and Ben, what should I be studying as I move into this sector? What's emerging? What's a good company? You know me, what do you think I could do? What would be a good starter role for me? But you did ask me something about not starting over and all part of this activity of the molecule, the atoms, almost anything, has admin, logistics, scheduling artifact, content curation. And if you look at what you've done in the past, and I don't care if you have to volunteer for the first couple of goes, you want to be able to recast yourself in more of a lateral move rather than I need to start all over based on all this work we've just talked about and understanding that, hey, there's some pieces I'm pretty good at and I'm willing to put my hand up and actually volunteer. And I mean, in the consulting firms, the way the fastest way forward is to volunteer for proposals. It's brutal. It's guaranteed to be at least two long weekends and some nights.
(26:21):
But you meet your local partners, directors, people find out, oh, he wrote that good, this piece or that, or they'll tell you what you want to work on. I don't think you can beat that. Kind of get out there, try it, get feedback. And all this now is so you can say to yourself, even though I'm 54 years old or whatever you are, no, I don't need to start as the entry level job. I could do something that's a supporting role based on what I know, and then work at that hard enough and just continue to morph into the field. Is it alright to offer you a cybersecurity example? There's a pretty red hot one.
(26:59):
Sure. Yeah, yeah.
(27:00):
So I would never pretend to be a cybersecurity ciso, but you know what? I've done so many of these projects now just from hanging around and have clients trust me, watch this trajectory. The first one was I was basically a golfer. I was an organizer, I helped schedule stuff. It was really on the periphery, but turns out I was willing to read the NIST and CIS standards, attended the sessions, found time, he took a little bit of hit on billable hours and stuff. And the next thing was working on what are called ttx tabletop exercises. Anyways, after a few of these, I never would claim to be a ciso, but you know what? I can teach the one-on-one course, I can tell you how to get started, what it looks like. But there's a progression where all I did was show up in what's around me.
(27:48):
And I really invite people to do this, look around, figure out if you're in a place where you got to stay in your lane and they'll yell at you. If you go talk to someone else, well that's another matter and maybe we have a different conversation there, but I think almost anyone is willing to accept a little bit of help. One of the other things that happens to you in cybersecurity is need insurance to do that needs to be able to do an inventory. What digital assets do we have? How many instances of PI? If you're willing to do some grunt work in Excel, guess what? And I hope you're sensing the dynamic. It's along the lines. It's pretty much the same as you're saying, Ben, drive to Portland, find the CFAs. It's just a different version of
Ben Smith (28:32):
It. Find the room and just get into that room. So Mike, I want to ask you another question here. And again, we try to do a lot of scenario kind of play and I think just there's a lot of things that you can learn from how you respond to certain things. So one situation we see a lot, especially some people that maybe they're nearing a retirement, but they want to move into a leadership, right? Maybe it's just to mentor younger employees, but they've never had formal management experience, which by the way, that's one of the big failings personally, just my own vantage point, we never really train managers. We train skills, but we don't train a lot of how to manage people and how to motivate them and how to work with 'em. And we just assume that because you're good at one job that you're going to just transition to management and be good at that job. But my question is, you've never had formal management experience and you want to get into leadership, how can I position myself for those roles without being set up to fail? I think the setup to fail is a big concern here.
Mike Dwyer (29:31):
Well sure, and just to underpin the seriousness of this, remember I went and got a master's degree in management. It's a big deal. But where I think start is unfortunately, I think the only thing we think of generally when we say manager is boss
(29:47):
And actually there's scheduled management, resource management. And so I think that if you are willing to help on areas like that, lemme step back a little bit. If you really know a sector and you have operated at multiple levels, I mean there's an element of assessment here. If you've been a line professional, a middle manager and an executive, you probably are in a position where you can offer leadership even if you haven't had training. But if you hadn't, I think you want to do that same gorilla approach that says what needs doing on the one track. And then the other track is most companies have a community day. Are you willing to take responsibility for leading a team if you'll do that and figure out who picks up who in the morning and all that stuff. Actually that's management and working with the people during the day.
(30:45):
And so I think we have to be careful not to just think that I'm going to go from zero to 60, that the next thing I want. If I've never done something more than be a white collar, an individual contributor, and I'm dreaming of running a Fortune 500 company. No, no, that's too much of a pole vault. But I think a segue that's using an understanding that says, well, management is actually managing processes, activities, this and that. And then if you augment it, I gave you an example of volunteer the team lead at the community day and corporation. But I also think this would be a great place. I don't care if it's the American management. I haven't been a MA, I haven't been in touch with them in a long time. Years and years ago I went to a course I've sent people there. But much like you said earlier about the CFAs, get yourself a group of managers, find out why not take a course. I don't care if it's at a community college. If you are doing things that say I am volunteering where I am or someplace that matters, that is doing management, like things that's managing something and I'm taking on some skills and getting some language and framework. I think we have a story.
Curtis Worcester (32:03):
Yeah, gotcha. Yeah, no, that's great. Another thing I think that we think about a lot is culture, right? Culture matters a lot, especially probably later in your career. And we all know some workplaces reward experience, others reward youth and speed. So how can somebody in this position evaluate whether their workplace culture will support a pivot or maybe if it's time to look elsewhere?
Mike Dwyer (32:32):
Well, I think actually that's one of those questions that has half the answer in it,
(32:36):
Curtis,
(32:37):
But I do want to talk about this a little little bit and I'll give you a couple of fun examples. I had somebody I knew in my circle that had had a long career in hospitals as a social worker
(32:48):
And ended up joining a hot startup and it was absolutely hilarious. I was so happy for 'em when the company was small enough, like 30 people and what they were were 29 pictures of 30 somethings and one guy who looked like Jerry Garcia, but in that particular setting, they loved his experience. There was no stress. They just understood he was here to talk about how he'd seen it done in different settings. So that's an example where you might be a minority, but it's absolutely comfortable. There's a welcome chair for you, but I think some other things we have to struggle with. I do push a little bit on people with some sort of techniques and tests. Don't use your experience to tell war stories and harangue people use your experience to say, what are we trying to do next? And what have I seen that needs attention now that's helpful.
(33:37):
Another thing Steve and I have been Steve Dubin and I have been joking about is I said, and then sometimes it might make sense to report to someone much younger than you, he said, right? And you made me said, even if it doesn't look like he shaves yet, but I'll give you an example of a woman I met in a public sector setting. She was doing process improvement coaching and she had a room full of public sector professionals. She was sharp as a tech. I said to her, wow, that was great work. Afterwards I was supporting one of the people attending, do you have an MPP or an MPA master public policy, master of Public Administration? She said both. So what I think the older worker has to understand is that just because someone, I tell 'em, even if you can't look at the person and just listen, you might hear the word more than you like, but understand, separate your sense that I have a long career and I should be the boss and just let the person who has the right handle on the helm do their thing and see how you can help.
Curtis Worcester (34:38):
Well that's great. And Mike, I want to keep going here. This is all super helpful. I want to go back to something we or you quickly mentioned before, but it's around networking. And networking as we know for a lot of people can feel very intimidating, especially if you've been in the same job or industry for decades. So you created a training that has been backed and promoted by the commonwealth of Massachusetts, and you mentioned that a little earlier. What advice do you have for retirees or elder career people or even just introverts who say, I hate networking.
Mike Dwyer (35:17):
I got you loud and clear, Curtis. There's a young technical person in my coworking space that when I mentioned networking, I could see the recoil. This is manipulation, this is evil. Instead what I'd say is, and we're going to talk introverts in a minute, but the fundamental dynamic I think is to let your curiosity outweigh your shyness. You know what, Ben? I would actually love to sit in on that CFA, it's
Curtis Worcester (35:50):
Really good. I just want the $10 lunch. I mean, come on, 10 bucks, that's a steal.
Mike Dwyer (35:55):
But to listen to true experts and as a community, that is really cool. But you don't want to put yourself in a difficult position. So surprise, surprise. I came up with something, I got a little table in my booklet somewhere that says, okay, let's do a little bit of a diagnostic. If you're scared and you've never done this before, my little table has three columns. The left hand column is scripted and safe that looks like this. I go to a lecture and there's a q and a afterwards. I can manage that. I don't to, we don't have to figure out what to talk about. We were just told what to talk about. And then you kind of move up the food chain and then you go all the way to the far right, like you mentioned the Chamber of Commerce for here at this Cambridge Innovation Center, there is a venture cafe every Thursday night over at the Kendall Square one, the one year MIT that is 300 caffeinated people. And you better know what you're doing.
(36:58):
You're just going to get drowned out or whatever. So the right thing to do first of all, is to get kind of a diagnostic, alright, I want to ease into this. Great, and I guess explained, do something that looks like that. But I also believe strongly that this business of shopping, intentionality, selection is good for us. And so what I recommend is some trial and error, and I've taken networking and come up with a 10 or a dozen rows that's say you got your classic networking, right? Your chamber of commerce, your rotary check out, maybe you should be doing one of those. But if you're a young gay, black accountant in many parts of the country that requires navigation, we want some identity networking, we want some folks like me and maybe some oldsters would want that. Other things you can do are, I have this concept of a lab feeling a little outdated.
(37:48):
Are we afraid of collaboration tools? What if Mike, Ben and Curtis download a copy of Slack and organize a golf tournament or a birthday party? What does that do for you? I want you to go from, wow, I don't know what this is to, hey, my first impression is I want you inside. And I saw it that these things are achievable. Anyways, I could go on with those other categories, but I think you see the idea that with a little bit of prep and work, and I always go back to this career budget and this is a wonderful thing where Steve Dubin and I can offer you a couple of points. He's saying, oh, if you're serious got to be out there at least once a week. His colleague Mike says, you know what, six or eight a year after two years, the cumulative effect, I mean obviously his is the blitz, right? I mean, you've got 50 shots a year, you got a lot of trial and error and you're meeting a lot of people, but that might not fit into your personality, your time. Your Curtis just had a child, Hey, we want you to go to things four nights a week.
(38:52):
But my point is that as few as six or eight a year, year on year, you're on a different path than someone who doesn't do that.
Ben Smith (38:59):
Absolutely. Gotcha. So Mike, I want to obviously ask the next question here, right? Because talking about getting in the room and kind of what rooms to be in that, but you have said that the best networking isn't transactional, it's relational. I hear the introvert person that you're saying like, no, it's evil. I think when you treat networking as transactional, it does sound very artificial and surface. And what's in it for me is that, but when you start talking relational, can you talk about that playbook for building real connections, especially for folks who are entering new industries or unfamiliar communities as we're talking about just opening these doors?
Mike Dwyer (39:41):
I do. And boy, I think you two should have a podcast.
Ben Smith (39:45):
No, that's a great idea. I like that.
Mike Dwyer (39:49):
First of all, always avoid the big ask. I mean, what you want to do, and my colleague Steve Dubin has some phenomenal techniques. Are you shy introvert who can get trapped by the verbose, whoever just calmly say, Hey, I was hoping to catch 10 people tonight. So glad that you were my third. Thank you. Low key. Keep moving. One of the things he'll say to you that I'm going to go back to what you said, Ben, about the CFA and the, I don't think you called it fresh meat, but highly attracted to the newbie. He'll tell you a story that one of his current clients, he met early in his business when he decided to rescue someone who looked a little uncomfortable at a networking event. And I think we should keep that in mind that it's okay to be rescued and it's okay to rescue.
(40:40):
And I do think in this workbook I I ask people to think about what's their mantra? What's there, why am I here? And it could be as simple as I'm thinking about other career options. Excuse me. It could be a little more evolved that says, I really want to know more about CFAs or this or that. One of the things to do I think is you can really ask questions that reflect curiosity and are flattering and comfortable to the listener. If you genuinely say, what book should I read? What class should I take? That's not something that sounds like a project to the listener. It's not off-putting. In fact, it's affirming that the person probably knows something that would be good to share and you can get about that business. So yeah, very much not transactional. In fact, having been in, remember I'll tell you that any kind of from manager up at Deloitte, you are instructed that every second Friday afternoon de minimis, you're supposed to look through some networking and contacts and think, how could I add value?
(41:42):
What would be truly of interest to these people? And eventually you get to a point where you're living your weeks knowing this Friday afternoons coming and you're literally harvesting, oh, Ben, wait till he sees about the CFA comedy standup. This is going to be ahas. You know what I mean? And that's very much non-transactional and really what the essence of there is. If you're doing that with people for a while and seeing them and caring about what they do and sharing what you think they might be interested in listening and so on. If you one find day say, would you take a look at some software I wrote or I got an idea for a business, it's much more comfortable. It could flow nicely. So how are we doing? Are we making a case here for taking that risk and doing some networking?
Curtis Worcester (42:32):
I think so I think we're trending in that direction. I want to talk about something else that I think has been a through threat a little bit here today, but I want to focus on it and that's mentorship. Okay, so we love that you asked a hundred people in your network if they'd meet with somebody who needed guidance and not a single one said no. I just want to ask Mike, what's your advice for finding a mentor without it feeling awkward or one-sided or even transactional? We were just talking about how do you go about really finding that mentorship?
Mike Dwyer (43:03):
Well, I think Curtis, if I can say, first of all, I always want to help people feel like they're not making a final choice. That this is not in anything. Let's keep this to where this is a pilot. So the first thing you want to do is about a mentor I think is you want to understand a little bit, am I trying to find somebody who could help me? Female executives we know from the Harvard Business Review, and there's still some navigation for them that may not be there for men. So they may be wanting to see someone who has been in their sector who can coach them in kind of a pointed way that says, here's how to play that difficult boss, this kind of thing. So I think a little bit of, and this could move and change through time, so a little bit of reflection and the like that says, really, am I trying to get advice about career, about how to navigate? Do I want a generalist or somebody who's a little more specific? And so that's some prep work that would lead to, would you mind having a coffee with me or this and that. I mean obviously I don't know that many people would say no, but be my mentor is kind of a lot for, it's an opening question. It's
(44:19):
Person really well. But if you say one of the things I mentioned, Salva University, the person who's in runs a career office down there has some wonderful work on informational. And so what that is about is it's safe for both parties. Yes, you're asking for a little more time. This is not just a five minute thing, but the person knows you're not looking for them to hire you. You're looking to understand what the role or sector is about how do you get into it. So you could start at one end of the spectrum, it could be as small as that and see if it goes anywhere. And at the other end of the spectrum it could be, well, I know this person was a president of a major consulting firm and to, she was able to handle a lot of juice, a lot of vaults, and I would really like to approach her about some sort of ongoing guidance kind of thing. So how are we doing? We finding our way a little bit.
Ben Smith (45:18):
And Mike, I'll just kind of echo and just share a personal story there too. I used to work for Camden National Bank and they had a wonderful organization and one of the things that they talked about was mentorship when I was working there, and especially as a younger person that wanted to grow their career and learn as much as I could, the CEO said to all the officers, all the president vice presidents, the assistant vice saying a whole officer group, this group is going to be mentors. We're going to mentor everyone in our organization. We're going to coach and we're going to get some organizational knowledge that we're all going to share with each other. And I think if we do this, we're going to create a leadership engine. Just I think Jack Welch and had kind of talked about the leadership engine a little bit, and that was some of the thought.
(46:08):
He goes, if you haven't had someone come up to you and ask to be your mentor, I want you to go find someone to go mentor. So I then wrote him an email right after that and said, well, if no one has asked you to be their mentor, I'd like you to be my mentor. So I reached out, it's like, if you're going to put it out there, I'm going to call you out on it. So I was the only one to ask him to be the mentor. So he took me to lunch and coffees and all those things. He's like the amount of knowledge I got from him in terms of just who I am, where my strengths are, not just talking about obviously what's happening in the organization, which would probably be inappropriate. Skipping eight lines of management responsibilities there and lines of command.
(46:53):
But to go talk about your personal journey and what he faced and applying it to what I'm facing and thinking about and all that. It was life-changing, right? Just kind of opened up so many doors and I appreciate him that Greg DFO was the name of the CEO at Camden National who just retired. But it's one of those of just even asking the question. I know he put it out there and there was a room that was there, but you still have to have a little courage to say, Hey, I think I'm worried of being a mentee here. And I had love for us to have coffee and can I buy you a coffee? And I know I'm not what the CEO's making, but I'll buy you a coffee. And he goes, absolutely. And just so happy to receive it and just happy to have that relationship in my life. And that was something that just opened a lot of doors. So I wanted to share that quick little story just of see for Mike and the listeners there, it it's kind of puts you out there a bit, but it really does help in terms of life connection and talk about real connection out there.
Mike Dwyer (47:56):
Well, you know what? Because this is a pretty sophisticated, you have pretty sophisticated podcast here. I'll just throw one little bit of intellectualism at you, one of my favorite social science papers of all times, remember in the dotcom, all of a sudden the dotcom was out attracting talent from big four professional services firms. So basically to cut to the quick, all those firms never had to worry about where partners and directors came from. It was like salmon spawning enough made it, there you go. So they actually commissioned, this woman named her professor used to be at London School Economics. Now she's somewhere in the us, Hermione Ibarra. And she did this phenomenal paper on how we learn and model and what she landed. And this Curtis is going to map right to your story. She said that if you're lucky, you do a monolithic model.
(48:50):
If you are a six foot one college football player and the partner in your firm is similar, you are going to give him permission to give you a little shove out in the hallway if need be. But you're going to get direct feedback attention and you're going to grow fast. But for the rest of us, it may take what she called collage modeling. We may be looking and seeing that, wow, that person didn't say anything in the meeting until the end, but she asked a question and we're all doing what she said. You know what I mean? Or Wow, that person was so prepared. I want to be like that. And so I think one element of this mentoring thing is to understand that we need, there's trial going on and we model behaviors and see which ones work for us and that if we're intentional about that and finding someone who is either a good kind of generally monolithic match or maybe a small cadre of people that, well, I like how this one does this and so on, and we can set about that work and try and improve ourselves and learn.
Ben Smith (49:51):
Yeah, absolutely. Awesome. Well, Mike, I want to ask another question too. And Emplana lives in an innovation world surrounded by startups, nonprofits, emerging economies. So obviously Cambridge is who we think about. We think about that. So talk about a little bit, how does that ecosystem benefit someone in their fifties or sixties who might want to bring experience to a smaller mission driven organization?
Mike Dwyer (50:14):
Well, first of all, if you need some jumper cables, go to some place. I'll tell you what, every once in a while, the MIT Enterprise Forum, my location is actually in Boston, but it's a spinoff from Cambridge Innovation Center, and there's two locations in Kendall Square, but you might want to just go to what's called a shootout. So every once in a while you'll see whether it's the mass challenge, and if you're anywhere near a university town, you get a shot at this. What you're looking for is a place where a few people are showing their business plan and getting feedback. There's an organization called the MIT Enterprise Forum that I used to be a member of. I have been a member of on and off, and then I think it changed its name to E forumm. But what's cool about that, imagine three, one to 2-year-old companies, they're past the angel money, but this is still touch and go. But they do have a product, maybe a couple clients and maybe there's 30 or 40 of us sitting in the audience, and we get an entrepreneur and residence from the forum. We get the Samsung VC guy, we get a few leads, people who lead our sessions, and we have the luxury of listening to a few of these shootouts breaking out into groups of eight or 10 and thinking about this stuff. Now, this would be applied if the pulse had slowed too much on our 55-year-old, this would be putting the paddles and
(51:39):
We start. And I think that's, I mean, doing something like that is just going to open your eyes. I mean, 10 years ago, I was seeing firms that say we're using drones to cut what used to be six to eight weeks of survey work into six days. And you know what the business plan said, we can actually charge the same money. They don't mind because getting done in 10% of the time. So anyways, that stuff is just where to go, how to do it now. Then secondarily on a more gradual, not for the paddles, not for the shot of adrenaline type thing or the biggest coffee you can buy, you may want to get somebody who's in one of these spaces, or the mass challenge is an incubator here in Massachusetts. So you might want to say to yourself, Hey, boy, I'd like to start going to that monthly subscription. Or I have a friend who's out, a really interesting coworking space that keep telling me about, well, how about next time they have a monthly social? Ask your friend if you can stop by and start taking a look around, but always under the heading of getting out there. But this is a little bit, remember, I can talk about portfolio because of who you two are, and this is a specialty, this is a specialty
(52:55):
Investment.
(52:57):
This one's not stock bonds, whatever this is. I'm going to take a tiny little track of time that's kind of exciting research, and I'm going to go put myself into some of these things and see what's going on and see how to follow up.
Curtis Worcester (53:10):
Yeah, no, that's great. Mike. I'll just speak for both of us here. This entire conversation has been so fun and super helpful. I do have a final question for you. It's going to be a little different than the ones we've been asking you so far. I have to ask everyone who comes on the show. So again, the name of our show, retirement Success in Maine, we're all about helping people find their retirement success here. So I got to ask you, when you get there, how are you going to find your own personal retirement success?
Mike Dwyer (53:39):
I am over, well over 65, age 65, and if the day job keeps being this interesting, even though sometimes it's hard and demanding,
(53:49):
But I mean, what I've done in the last week, no joke, is cybersecurity, cloud computing. I got a cert from AI six years ago from MIT Sloan, the business side of it. But it was, and to me, I guess my answer is potentially gradually easing into more of a retirement. But as long as all this stuff I do with people like you and labor market research and skills development informs the day job and the day job makes me be able to say to somebody, here's what you want do. So far, I'm finding it hard to walk away.
Curtis Worcester (54:23):
Hey, there's nothing wrong with that. Nothing
Ben Smith (54:25):
Wrong
Curtis Worcester (54:25):
With that.
Mike Dwyer (54:26):
Yeah,
Ben Smith (54:27):
I love that. And Mike, I want to, again, as Curtis said, thank you for coming on our show. I do want to plug for those that are listening and maybe interested, you can learn more about Mike's work@planacareer.com and also connect with Mike on LinkedIn. So Mike's very active there, open to chatting, so you can always kind of connect with him there. So Mike, thank you so much for coming on. We really value the conversation, your insights today. It was a lot of fun.
Mike Dwyer (54:54):
Well, thank and thank you for your enormous contribution to it. Thank you.
Ben Smith (54:58):
Our pleasure. Alright, we'll catch later. Curtis learned a little bit more every time talking about changing work roles without starting over, and it's something we're hearing from our clients a little bit here and there. So it's good to get expert in and have that conversation. So absolutely. I know we learned a lot from Mike today. For those listening, you can go and go to the links of then Emplana career.com LinkedIn. We'll have that in our blog. So you can go to blog dot guidance point llc.com/ 1 1 8 for episode 118 and check it out there. But again, we encourage you to go connect with Mike and if there's something he can help out with, we know he's serious about doing it, feel free to do it because we'd love for you to improve and get to that work opening an opportunity that we know you're interested in. So thanks so much for listening. We really appreciate you and we'll catch you next time.
Outro (55:58):
Ladies and gentlemen, you've just listened to an information filled episode of the Retirement Success in Maine Podcast. While this show is about finding more ways to improve your retirement happiness guidance point, advisor's mission is to help our clients create a fulfilling retirement. We do financial planning so that people can enjoy retirement and align their monetary resources to their goals. If you are wondering about your own personal success, we invite you to reach out to us to schedule a 45 minute listening session. Our advisors will have a conversation with you about your goals, your frustrations, and your problems. Make sure you check out guidance point advisors on our blog, Facebook and LinkedIn, and you can always check out more episodes of this podcast on iTunes and Spotify and of course, keep on finding your retirement success.