How To Navigate a Second Career as a Content Entrepreneur

Carl Landau and Bernie Borges host podcasts that speak to “second acts.”  They are navigating the road of a second career as a content entrepreneur.

In the I Used To Be Somebody podcast, Carl speaks to people who retired from one career and pivoted to new and sometimes surprising careers. It’s what Carl did – starting a podcast after retiring from his magazine and event businesses. He even refers to himself as “unretired.”

In The Midlife Fulfilled Podcast, Bernie speaks to people who have had a lightbulb go off and transformed their lives to do what they love. Bernie’s doing that with Midlife Fulfilled while still working a demanding 10-hour-a-day marketing job.

In all those interviews and personal experiences, they have learned a lot about career pivots and post-retirement. Now, they share what they’ve learned for expert creators interested in a second (or third) career as a content entrepreneur.

Motivated to switch

Waking up one day and realizing their current career doesn’t fulfill them is a common theme among guests on The Midlife Fulfilled Podcast.

“When we are young, we sometimes follow a path that has been predetermined for us. Sometimes, we embrace this path enthusiastically. But, what often happens a little later in life is a realization that our current values don’t align with the career that was essentially chosen for us,” Bernie explains. 

That lightbulb can illuminate at any point in midlife. (Bernie doesn’t define midlife as a chronological midpoint in someone’s life because no one knows when they’ll die. He sees midlife in phases, starting in someone’s 30s and going as long as they have their health.)

“Sometimes, an individual commits to an entrepreneurial venture that is driven by a passion to solve a particular problem in the world because it aligns with a current value,” Bernie explains. “In other cases, they are laid off from a corporate job, and this event becomes a pivotal moment to embark on an entrepreneurial venture.”

Carl, who has spent over three years in unretirement, writes, “There are just a few times in your life that you can naturally reinvent yourself … 1. after you graduate from high school or embark on a career path and 2. life after the big job.

He experienced the latter.  “I knew that I didn’t want to continue with a full-time career, especially being an entrepreneur my whole life. I hit a certain point where I’m like, I’m done … I literally would have nightmares about (work),” Carl says. 

Think about all facets of your life

As you go on your entrepreneurial journey, examine all aspects of your life.

Bernie developed a pillar strategy – five areas of reflection to understand where you are now and where you want to go. These encompass health, fitness, career, relationships, and legacy. 

“As we age and our lives unfold, we evolve in so many ways. Our values change. What was important to you in your 20s may not be as important to you in your 40s. The relationships you had in your 20s may be different than in your later decades,” he says. 

“What do you value most now? Is it money? Title? Awards? Popularity? Family time? Improved health? Benchmark your values against each of the five pillars to determine your level of fulfillment in each pillar. Don’t expect to be 100% fulfilled in each pillar,” Bernie says. 

Also, expect your strategy to evolve as you age and progress through different levels of fulfillment. “It’s one reason that at the end of each podcast episode, I say, “If you’re 80% fulfilled, you’re doing great!”  

Manage expectations

Quitting your career cold turkey and starting a successful content business isn’t likely to happen.

“It takes a long time,” Carl says. “You don’t start something new, and the next day it’s great.”

Just as you did early in your traditional career, it takes time to get people to pay attention to you and your work and return your emails and phone calls.

That can be tough for overachievers who have been successful in their careers for a long time. “You have to give time to it and be patient with it,” Carl says.

Recognize you’re now a beginner. He tells of a recent podcast interview with a former district court judge who is now a singer-songwriter. She went from bossing everybody around to standing on a stage on open mic nights, waiting for the audience’s response. “She was terrified by the whole thing … All of a sudden, you’re a neophyte. You’re the person that doesn’t know anything.”

That’s when a lot of entrepreneurs give up (or never start.) The successful recognize they need to learn what they don’t know and be vulnerable in the process.

In managing your expectations, Carl also advises you to avoid comparisons. “You are the only one that judges how well you’re doing. Don’t judge yourself by what other people are doing. It’s much more personal satisfaction and working at your own rate of how you feel good about it,” he says. 

Carl wrote a blog article last year with lessons he learned after spending three years in unretirement. Here are some excerpts:

• Sleep matters. With less stress in my life, I sleep so much better. I used to sleep on average about 5.5 or six hours a night. Now I get my full eight hours of sleep plus a short afternoon nap sometimes. Sleep is so important for overall health.
• Exercise matters. I play pickleball four days a week now. And I walk 10,000 steps a day on the non-pickleball days. I’ve lost about 8 pounds this past year. I stretch/meditate (with my cat Felix) 20 minutes every day and love it! I feel much better physically and mentally.
• Friends matter. I’ve reconnected with several friends from my childhood and 20s and visited them. Since my career took me out of town a lot, I didn’t have much time to meet people locally. Now I’ve got more local friends than I’ve ever had. Just joining a pickleball club gave me a dozen new friends that I see all the time. As you get older, an active social life makes a huge difference in your state of mind.
• You matter. Learn how to say NO. I simply avoid negative people and things I don’t want to do. No more endless Zoom calls and I’ve stopped doing online presentations. (Do people really want to watch three talking heads on a YouTube video?) I spoke at a live, in-person conference last month in New Orleans and loved it. I don’t want to live in an only-virtual world. I want to make real connections with inspiring people, and I don’t need to do it only online.

Embrace your vision

The Midlife Fulfilled Podcast guests, to a person, have some fear when they take a leap of faith to start their own business, yet they also possess confidence.

As Bernie explains, “They have shed the constraints that were on them previously, flying free like a bird without a safety net. And the journey alone is exhilarating to them, so they keep going. Work no longer feels like work at this point. They define their own success without caring what others think about them because they are aligned with their values.”