F50 Issue #30: September 3, 2024
Reaching the Summit of Your Dreams: One Baby Step at a Time
“Only you know what you're capable of and you'll never find out if you don't try it.” — Dierdre Wolownick
The trailer for a documentary film called Climbing into Life opens with a gorgeous mountain view, set before a background of brilliant blue sky. Sheer rock faces jut straight out of the ground, skirted by velvety green stands of trees that gently flow into the valley below.
Then we hear Dierdre Wolownick’s voice telling her story. She’s the mother of Alex Honnold, a world-famous climber who stars in a documentary film called Free Solo. In her late 50s, early 60s, she started rock climbing so she could be closer to him.
As she explains in a CBC As It Happens episode,
"[Alex] would talk and talk about where he'd gone, what they'd done, who he did it with, and I didn't know what he was talking about, which is not a good way to relate to anybody….”
Now, like her son, she’s the star of a documentary film, and she doesn’t let age stand in the way of her dreams and ambitions. In the trailer for Climbing into Life, Alex proudly exclaims,
“I’m very pleasantly surprised by what Mom has done in the second half of her life.”
Even if you’re not a fan of extreme sports, Deirdre’s story has lessons for us all. If you’re considering freelancing after 50, you might feel like you’re looking up at an impossibly high mountain with unfamiliar vocabulary and equipment.
But that’s why we’re here — to help you reach the summit! Let’s explore five questions to ask yourself when pursuing your own dreams.
Five Questions to Help You Reach the Summit of Your Dreams
1. What "mountain" do you dream of climbing?
On the Climbing into Life website, Hannah Hale says, ““Even though Dierdre spoke seven languages, played at least 3 instruments, was an oil painter/artist and prolific writer, she still wanted more.”
Do you feel like that too? Maybe you’ve had a long, successful career in a certain field, and others think you should retire. But you still feel like you have “mountains to climb.” Well, the first thing to do is identify that mountain and plan to climb it!
For example, if you’re interested in freelancing and are having trouble choosing a certain niche, try the “Three Circle Exercise.” Craig described it in a recent Freelance After 50 video.
It’s built on a Venn diagram with three circles that intersect in the middle:
- First circle = work passions you’re interested in
- Second circle = your skills and experiences
- Third circle = opportunities that are available for you.
Your sweet spot is where those three circles intersect. Give it a try and see if it helps you define a potential dream career.
2. What (or who) is your inspiration?
Getting closer to her son was Deirdre Wolownick’s inspiration for rock climbing. And you may have similar reasons for beginning a second-act career. Many people who begin freelancing cite “more quality time with family” as one of their main goals.
Or maybe you’re inspired by someone in your community who works as a freelancer. If you’ve previously worked in a corporate job or a brick and mortar business, freelance freedoms like a flexible schedule and the ability to be your own boss can seem enticing.
The freelancer who enjoys a leisurely walk in the middle of the day while others are stuck at work is enough to make many people say, “I want to be like them!”
3. What's holding you back?
Sometimes we stand in the way of our own dreams, keeping us rooted to the ground when we’re longing to ascend. Take out another sheet of paper and list all the reasons you might hesitate to pursue a freelance journey.
Decide if there are any factors preventing you from simply starting. If one of the main reasons is fear, take comfort in this quote from a Los Angeles Times article:
“The most important decision is to start,” Wolownick said. “Once you start and decide you want to do something, it can be powerful. I say, ‘Just try it! Try it! You never know what might happen.’ ” A homemade sign in French in her home office proclaims: “Vouloir, c’est pouvoir.” Rough translation: To want something, is to be able to do it.
4. What do you need to “pack” for your journey?
When you filled in the circles of the Venn diagram, maybe you noticed that you’re missing a few essentials to make your freelance journey ideal. Even if you have extensive skills and experience, you might need more so you can build a stronger, more fulfilling career.
Here are a few extra things to pack and people you might want to bring along with you:
- Relevant resources, like books, articles, blog posts, and podcasts about your chosen niche
- Additional training like YouTube tutorials, online classes, and webinars
- Online or in-person groups where you can meet with freelancers who have traveled further down the road and up the “mountain”
- A mentor or coach who can guide and challenge you to continue your journey.
5. What baby steps can you start taking today?
In the CBC As It Happens episode, Deirdre Wolownick shares these inspiring words:
"You have to think about where I was 10 years ago. I was lumpy. I was working all the time. I didn't have time for this. I didn't think I could do it….
"But you never know until you go try. You know, it turns out that you could do anything you set your mind to if you just approach it by baby steps, you know, just backwards engineer what you want to do."
With that in mind, think of one baby step you can take today. For example, if you’re thinking about pursuing a freelance career, start by watching Craig’s Freelance After 50 video and remember his advice:
“It’s never too late to start something great!”
Insider Resources
For more inspiration, check out Deirdre Wolownick’s book, The Sharp End of Life: A Mother's Story:
"The author proves that age is just a number and that determination and grit can take a person to unexpected heights. For her, that meant conquering El Capitan at the age of 66. Wolownick's story of her drive to push her physical body beyond her mental limits will serve as a stimulant for those yearning to do more with their lives. A motivational tale of a woman who overcame her biggest critics, including her inner self, to achieve one dream after another." — Kirkus Reviews
Did You Know?
“Research suggests that learning new things as you age may be key to keeping your cognitive skills sharp—and that middle-aged and older adults may be just as good at learning as younger people are.” —
In a podcast interview from the American Psychological Association, Rachel Wu, PhD, “talks about why lifelong learning matters, how adults can learn more like kids, why feedback and failure are important, and what types of learning opportunities to seek out.
Check out the interview for advice on how “you can learn new things at any age”!
Here’s to lifelong learning and reaching the summit of your own dreams!
Until next time,
Co-founders of Freelance University
