You’re ready for your second act

In this episode, hosts Whitney Reagan and Dan Sharkey explore the pursuit of a “second act.” They discuss how to identify when you are ready for a career reinvention and why a solid financial plan can be an important part of making those transitions with confidence.

Learn how to navigate career fluidity, the importance of maintaining an objective perspective and how to utilize your existing network to explore new, meaningful opportunities. Whether you are proactively seeking a change or responding to an unexpected job loss, discover how a thoughtful, integrated financial strategy can help you pursue your passion while considering your long-term financial security.

Transcript

Whitney Reagan: Today we’re going to be talking about your second act, what that means to you and when you’re ready for it.

Welcome, everyone. We’re back with the dynamic duo. Dan, how are you today?

Daniel Sharkey: I’m great. Thank you. How are you?

Whitney: I’m great. Today we’re going to talk about how you know you’re ready for your second act. In the more traditional sense, it’s talking about the second half of your life and retirement and what you’re going to do in retirement. But today it’s a little different, and it’s more about reinventing yourself and maybe choosing a different career or something that is drawing you to a different type of job that’s more meaningful.

Have you had that experience with clients recently?

Dan: I’ve had that experience all the time, and I think people think about work differently. This is not the generation or any of our clients really, who are working for the same company for 50 years and then getting a gold watch and a pen on their way out the door.

The world is much more dynamic, and the world is much more fluid these days. I think part of it is that the nature of the relationship between the employer and the employee is materially different. So that has created this sense of trying to figure out what comes next. And I think what we’re here to talk about today is how you can leverage understanding your plan to make sure you can make those decisions with confidence.

Oftentimes, people feel stuck because they see a dollar amount, and they just don’t think their life is going to work if they have to take a 30 or 40% pay cut. What if I want to go back to school and become a gym teacher? Every time that I go to my kid’s school, I’m like, man, I chose the wrong career. This guy’s got it made.

Whitney: You want to be a gym teacher in your next act?

Dan: Oh, man. It’s the best. The elementary school gym teacher—that is like the pinnacle of living right there.

Whitney: Ah, it would be fun.

Dan: But anyways, these are very important things to think about, because what we talk a lot about and if you’ve heard us on the on this podcast before, if you’ve ever been in a client meeting with us, it comes up all the time is what is the money for and what are your goals look like? And sometimes those are connected and sometimes they’re not.

But there’s always an impact if your goals change as to how your money is going to be used or not used to support those goals. So, this is an important part of discovery that we use with all of our clients. And it’s an important thing for people to think about. You don’t want to wake up at 70 realizing I really missed my opportunity to do the thing that I cared about the most. So that’s what we’re here to talk about and hopefully enlighten people as to how they can leverage us to make that a reality.

Whitney: And some people just like to work. Maybe the idea of retirement scares them because they’re like, am I going to be bored for the next 30 years? Maybe it’s retiring to more passion work, retiring to something that doesn’t feel like a job, but is actually also giving you some kind of income.

Dan: And just redefine what you want to do with the rest of your remaining days. A client said this once to me, and I think I’ve referenced it before, but I’ll say it again, putting my energy into something else. That could be a second career, that could be volunteer work. You know, work provides a tremendous amount of dignity.

It keeps you intellectually stimulated, and it doesn’t necessarily need to be entirely focused on a paycheck. I mean I often think about the careers that we have and what would come next when we eventually reach that day. And I’ve personally always been drawn to academics and being able to teach, maybe.

And how can I begin to lay the groundwork for that second career, now? And that’s one of the key things that I’ll come back to, and that is understanding what your plan needs to be viable. And also, are you doing the things today that will allow you to transition in the future at some point in time?

Now there are going to be certain tradeoffs, but when you have that awareness, you find a tremendous amount of clarity to be able to do and make decisions that you wouldn’t have otherwise considered.

And it’s really important to be able to combine this idea of taking the data and what it’s telling me, having an honest assessment of what it’s telling me, and also a realization that what’s the most important thing?

Whitney: So, I also have another example, a real-life example where I have two clients, in fact. They were thinking about different passion work, starting their own business or starting some consulting work, but they were still at their corporate jobs and their position was eliminated. So, they were kind of forced then to go and examine and look at doing this second act, which ended up being a blessing in disguise, because once we worked through the plan, we knew that they could do it, but that just gave them the little push or nudge that they needed.

Dan: Absolutely. So, if you have an advisor, or if you don’t have an advisor, you should get one. But if you don’t have one, how are you going to know whether or not the way that you’re living or what your future aspirations are can really take hold if something does change on the work front?

And to your point, we see that story happens over and over and over again in which a decision is made that’s beyond your control but intimately impacts you, such as being your position of work being eliminated. But if you understand what it takes to live, you understand what your options are.

You understand how your current wealth can support an event like that. Well, then you can feel kind of freeing to know that well, this is an unfortunate event. I didn’t really want it to happen, but now that it has happened, what comes next? And you can take that much needed breath to assess your options and determine, do I go back to what I was doing previously, or do I go become a gym teacher or some other version of whatever it is that you care about?

And I think that’s really, really important. And I think it’s really difficult to see that when you’re dealing with it in your own four walls. I’ve made this comment before and I’ll just reiterate it. The biggest advantage that we have as financial planners and as advisors in families relationships is an arm’s length distance from the actual money. The ability to see that clearly without the emotional attachment of I’m not going to walk into the same building I’ve walked into for the last 25 years, is our secret power.

It’s the surgeon not operating on their own child problem, right? You have that distance you’re able to see clearly. You’re not emotionally tied. You have no baggage. You don’t see friends and colleagues and memories. You see numbers and what that creates as a result. That’s tremendously freeing.

So, when you have that partner and the ability to have that conversation in which that person can see all those things with clarity that’s very difficult for you who’s emotionally living it to see, you can get a tremendous, tremendous benefit out of it.

I don’t want to downplay the loss of a of a career or anything like that or the sacrifice that may need to be made. However, if you can calibrate whether or not that sacrifice is worth it and you’re going to be okay, that’s tremendously empowering and tremendously valuable.

Whitney: You mentioned the generational shift in how people aren’t at their jobs for 30 plus years. And there’s flexible work, there’s hybrid work, there are different hours. So, the days are changing because of how we are working. And I also think that it’s interesting. It’s almost like the age of the side hustle.

There’s a lot of people that are doing things on the side, think like Etsy shop or if you’re doing some consulting work on the side, that is also an option if you’re fearful of leaving a corporate world or your corporate job because you don’t want to lose that income, you can start doing some side hustle and see how it works and see how—does it give you passion? Does it give you more meaning? Is that something that you want to do?

Dan: Absolutely. And don’t ignore the network of colleagues that you have built up depending upon what your trade, craft, job is and reach out to them to see whether or not there’s something like that available. I see some of the happiest clients I’ve had, have retired, quote unquote, in their late 50s and early 60s, but used the leverage of their network to go find other lucrative opportunities that may not have historically existed.

There may be a little bit of travel involved, but it’s less of a day-to-day grind and you’re able to really hone in on, after all this time in the corporate world or in the blue-collar world, whatever your area of expertise is, the ability to do something new. I think—and I don’t know how you feel about this—but I find that oftentimes it gives people a second shot of energy.

They’re reinvigorated to go do something new. And no matter what your career is, unless you’re truly passionate about it, a 30-year career is a long time to be doing the same thing over and over and over again. So, if it’s something that you’ve been thinking about, if it’s something that you know that you want, if you’re clear on your expectation, make sure you give it the proper weight and don’t put it off until tomorrow.

That does not mean that you take the leap the second you hear this podcast. But have you put the steps in place? Have you understood what it would take if you took a 50% pay cut? Or if you had to take six months off to find yourself or things of that nature. Those are things that you should know now.

And you may decide, look, I don’t really want to do it yet. But the sooner you can lay that groundwork, the better off you’ll be when the time comes.

Whitney: And I think talking with a financial advisor so you can actually visualize the plan, see if it’s viable. And another important thing is talking about it with your spouse or partner or someone meaningful. Because there’s often times—Brian Leitner, have you ever heard his blind spots presentation? It’s fantastic.

He talks about how he’s thinking about when he retires and his second act, and he didn’t know what he wants to do. But his wife Melissa says, “Well, I know what you’re going to do. You’re going to be a personal trainer for special needs kids.” And he was like, “How did you know that I would want to do that? That sounds fantastic.” And it’s beautiful how much somebody that’s meaningful to you knows you almost better than yourself.

Dan: And that is another example of the distance that I’m talking about. It doesn’t need to be you and me. Right? The financial advisors sitting in office with that distance. But some people can’t see it—most people, me included—cannot see it for themselves.

Whitney: Excellent points. I hope everyone liked what they heard. And if you did, please like, subscribe or follow wherever you listen to your podcasts and we’ll see you again next time.

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