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đŸ’„ The Demotion That Saved Oprah’s Career and The Woman Who Turned Minimum Wage Babysitting Into A Book Deal

After our recent survey revealed that 82% of you want help integrating AI into your daily workflows, we knew we had to act!

If there’s one big takeaway from the most successful AI case studies we’ve found over the past few months, it’s that they don’t waste time obsessing over what tech-stack they use. Instead, they’re the ones who take a step back to think strategically about how they get work done, and do so as a habitual and non-negotiable part of their job.

So to help you make this a non-negotiable part of your job (or business) and provide the automation assistance you seek, we're opening up 5 free 1-on-1 AI Workflow Strategy Sessions exclusively for our readers over the coming week. You can learn more and apply for a slot here.

Now let’s get this show on the road.

Beware of many-sided mediocrity

If you’re not in the tech world, you may know Peter Thiel as the guy who went viral in June after he hesitated to answer a question about the future of the human race. But he is better known in the technosphere as the leader of Founders Fund, one of the most successful venture capital firms of all time.

Mario Gabriele at The Generalist recently spent 18 months studying Founders Fund, interviewing over a dozen key figures, and conducting extensive data analysis, to find out what has made them so successful.

One question he posed to the team at Founders Fund was: what is the biggest lesson you have learned from working with Peter?

As Mario tells it, "Almost everyone who I asked at Founders Fund, 'what are the lessons you got from Peter?' Almost always the biggest one was like, 'find your comparative advantage and then specifically make sure to do that to the maximum. Take out everything else and just lean on your strengths as much as you humanly can.’”

Find your strengths, lean on them to the max, that’s the secret sauce.

As Thiel himself once wrote, “Instead of pursuing ‘many-sided mediocrity’ and calling it well-roundedness, a definitive person determines the one best thing to do and then does it."

If your weaknesses are all you pay attention to then “many-sided mediocrity” may be all you ever accomplish.

And this is one thing that both Oprah Winfrey and Thiel can agree on


 

Think in terms of trait-market fit

At just three years of age, Oprah Winfrey was already interviewing her dolls and the crows on her grandmother’s fence.

By sixteen, she landed her first job reporting the news.

In her early thirties, her talk show won two Daytime Emmy Awards.

Her story seems like it was written in the stars by destiny itself. 

But this narrative, while it sounds clean, is misleading. 

At first, reporting the news really was just a job for Winfrey, not some magical calling, and it was a job that Winfrey herself admitted she was ill-suited for in a commencement speech for Colorado College in 2019:

“I got my first job in radio at 16, got on tv at 19, and every day I said ‘I don’t know if this is what I’m really supposed to be doing.’ But my father was like: ‘You better keep that job!’ At 28, it wasn’t working out on the news because I was too emotional. I would cry while interviewing someone who had lost their home.” 

So let’s get this straight: for the first 13 years of Oprah Winfrey’s professional career, she (1) wasn’t sure if TV was the thing she was supposed to be doing, (2) kept the job because of the pay and stability, and (3) was being told she had a weakness that meant she wasn’t good at her job.

In light of that feedback, what would most people do? 

I think many of us would be tempted to iron out the weakness, right? To dampen our emotions and become a more serious news anchor. It’s not clear whether Winfrey failed or simply wasn’t interested in “fixing” her weakness, but she was certainly disheartened when her producers axed her position as a result


“I was told that I was going to be talking on the evening news and put on a talk show, and that was a demotion for me at the time,” Winfrey recalls.

But that so-called demotion turned out to be one of the best career moves in history. All of that emotion that supposedly got in the way of the news? The talk show audiences went crazy for it. Within four years of the show’s national launch, The Oprah Winfrey Show was routinely attracting 15–20 million viewers a day.

Emotion was no longer a weakness, it was a strength, a superpower.

The truth is that we don’t have strengths and weaknesses for the most part. We have traits. These traits can either become strengths or weaknesses based on the environment in which we express them. Imagine where Oprah Winfrey would be today if she continued trying to build a career by getting rid of her emotions?

The trick is to identify what makes you, you, and then go find a game to play where your youness will be an asset instead of a hindrance.

This doesn’t mean you can’t change or that you shouldn’t work on your flaws. It just means that figuring out the arena in which your natural attributes have the greatest odds of shining is always the much higher leverage opportunity available to you. 

This is much harder to do than it looks, but even more effective than it seems, as one of the internet’s most successful content creators explains


 

What is easy

Chelsea Anderson is the self-proclaimed “Michael Jordan of babysitting.”

Since posting her first Instagram reel in November 2024, her account has amassed 960,000 followers. She will almost certainly end up going from 0 → 1 million in less than a year.

In of her recent reels, Anderson revealed how she was able to achieve such rapid growth: “My mom used to always talk about how we value the least the things that we are very good at and that come easily to us, and we value the most the things that are hard for us, that we can't do. And because of that, we tend to really strive to get better at the things we're bad at, because we think those things are so valuable, and sometimes we don't even think to try to cash in on the things that are easy for us.”

When Chelsea decided she wanted to become a content creator, she thought about her Mom’s advice. “So when I set out to be a content creator, I said to myself, ‘Okay, what do I want to do? I want to make content. Great. What do I want it to be about? I don't know! I just know I want to be able to do a lot of it and I want it to be easy for me. What am I good at? What comes easy to me? Babysitting. Okay, great. Let me tell some of my babysitting stories. Boom! Six months later, here we are. I have a book deal. I quit my full-time job’” 

Find your strength
 check.

Lean on it to the max
 check check.

“[Babysitting] maybe didn't seem super valuable to me at the time when I was making that video,” Anderson reflects, “but I knew it was easy for me. Which probably means it’s valuable to somebody else, somebody that it’s hard for.” “Making a lot of money, being successful, it doesn’t have to be hard. We just think that because we look at people who did it in a way that would be difficult for us.”

Anderson’s takeaway is simple


“Take a look at your life, what is easy for you?” “Double down on it.”

 

New project who dis

Shoutout to Louise who recently kicked off a new project with a fresh Dot Grid book.

While the right constraints can be a gift, tackling your creative goals without a steady supply of Action Method tools is like trying to run a marathon in flip-flops, a limitation with only downside!

 


 Let’s partner with them

“OK, but
”, you may protest, “what do I do when I need to accomplish something where a weakness is unavoidable?”

Back when Scott Belsky was leading strategy at Adobe, he was asked how the company decides whether to create its own AI models versus relying on those built by others.

“Yeah I think for the areas where we are world experts, we’re going to be able to deliver a better end-to-end experience with our own models,” Scott responded. â€œThe litmus test for my team is—if it's something that we believe we can do better than anyone else in the world, it's our responsibility to do it. However, if it's something that is commoditized, or some other company is definitely going to invest in more and always have something better than we have, like
 let's partner with them!”

Keep this strategic framework bookmarked in your brain:

If you are or can become exceptional at something, you have a responsibility to do it. But when you require help on something that represents a weakness for you (especially a weakness that is unrealistic or undesirable for you to work on), go team up with people who are already excellent at that thing.

Play to your strengths, partner on your weaknesses. It takes a village to raise a big idea!

 

Thanks for subscribing, and sharing anything you’ve learned with your teams and networks (let us know what you think and share ideas: @ActionDigest).

 

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This edition was written by:

Lewis Kallow || (follow)

With input and inspiration from:

Scott Belsky || (follow)