Finding the Next Lilypad: Navigating a Career in Content Creation

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Here is my weekly email with some insights and ideas pulled from conversations I had on my podcast.


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Finding the Next Lilypad: Navigating a Career in Content Creation

Every career starts with a leap of faith. Like a frog jumping from a dock, praying that the first lilypad is within reach, you set a target, hold your breath and just dive in. 

Along the way, there will be more jumps like that, but as you go things will start to get a little easier. You become more calculated, and more direct, and find ways to avoid exhaustion and burnout. 

“By the end, you are in retirement on the other side of the pond.”

That’s Gigi Robinson, explaining her lilypad metaphor to me in a recent Success Story podcast. 

The 21-year-old self-made social media tycoon has had her photography on display all over the world (the Met? No big deal for Gigi), been featured in Forbes, modeled for Sports Illustrated, and has used her platform to lead the discussion about body positivity and living with chronic illness.

It’s sometimes hard to know how to go about starting in the world of content creation but as Gigi lists off a baker’s dozen accounts – Instagram, TikTok, Twitter, Snapchat, Pinterest, Facebook, LinkedIn, and a bunch more for her podcast – she explains how you have to carefully think about each step, and never stay on one pad too long.

Below, we’ll distill my conversation with Gigi into a roadmap for the next wave of artists that want to get into content creation.

Turning passion into profit

Think back on your teenage years. Were you planning out your next career move? No, me neither. That’s what sets Gigi apart, who knew she wanted to be an artist all along and was already probing the system for ways to make a living. 

After being diagnosed with a chronic illness at the age of 14, she worked diligently to bring positivity to the world through her art, personality, and content. 

She hosts a Spotify Live podcast called “Everything You Need Is Within,” releases “The Creator Chronicles” newsletter, has a top-secret book project and has worked with major brands all over the world including TikTok, Tinder, Tommy Hilfiger, Timberland, Ralph Lauren, Amazon, and Kendra Scott. 

Know your why, but know it ten layers deep

“Make sure that on that journey, you are okay with finessing or adjusting that true why.”

Even at her young age, Gigi understands that what you want one day might not be what you want tomorrow. When she was 16, her whole life was photography. It was taking photos of landscapes at night, and submitting them to every contest she could – regional, national, global, it didn’t matter. 

Now, a few years later, she has come to realize that it wasn’t just photography. Her story, just like everyone else’s, goes deeper than that. 

She wanted to help people with body positivity. She wanted to be a role model for those going through chronic illness (Gigi suffers from Ehlers Danlos Syndrome). She wanted to employ people and run a whole team of women.

Now she does all of that.

Getting to understand why you do something, and what factors may have gone into the decision in the first place, will allow you to navigate any challenges that fall in your way. I’ll quote her again, explaining how to start to discover these answers:

“Why do you do what you do in life? Answer it once, and then ask yourself, why do I think that’s important? Why is that important to me? Write that out, and whatever the answer is, you keep going down this funnel until you get the true meaning.”

Gigi says she does this once every quarter, reevaluating her direction and her passions regularly. It’s a good lesson for anyone – I know I will be doing it more often. The things that drive us can change at any time, at any age, and for any reason.

Don’t stay for too long

When she had the choice of where to go to college, there were only three destinations she considered: New York, where she had grown up, Los Angeles, and Miami. To her, staying in the same place wasn’t an option:

“If you spend your whole life in one place, it can limit you from a lot of your growth.”

This point doesn’t even need to be geographically focused like it was for her. The idea of staying somewhere safe and familiar – just because it is safe and familiar –  will stunt your potential. 

Whether that is a city, a job, a relationship, or something else, staying in one place while your ambition is desperately trying to pull you in another direction will only hurt your long-term growth.

Be confident in your failure

“Get over yourself and start posting.”

I couldn’t have put it better myself. Gigi readily admits that she deals with stress and anxiety regularly but she’s determined to continue to push forward even through potential failure.

It’s something that so many people struggle with, especially when trying to make a content creation career. After pointing out the studies that have shown likes, views, and follows on social media create a dopamine effect in your brain, Gigi explained what she focuses on instead.

“None of that matters to me. I care about the community. I care about the people I serve.”

So, then, the answer is to create or find that community to serve. Instead of worrying about who will like your post, or whether it will go viral, create content that is of value to the people that you care about the most. The people you are there to serve. The rest will come naturally and if it doesn’t, “you know what exists? Boosted ads.”

The four pillars of any project

So when she gets a bout of inspiration, does she have a specific production pipeline that it goes through? Nope. Like so many other content creators, much of her value comes from her authenticity. 

If Gigi is at a doctor’s appointment, she might take a photo of her hospital bed, so that anyone else going through an illness might be able to relate. 

Instead of working out exactly how to maximize views, reach, or engagement, she asks a few simple questions:

  1. How can I out-do my last project?
  2. How can I make this better than any of my projects?
  3. How can I have fun?
  4. How does this represent me, my brand, and the people I work with?

If you can answer these questions positively, then this is something that you should pursue. And that’s not just for brand advertisements – it’s for anything. If you are creating content, it needs to be authentic to you and at least try to be the best thing you’ve ever done. Competing with yourself is a great way to grow.

Navigating creative burnout

Burnout at any job is a serious risk. I face it often myself after a particularly long week. When you start an exciting new endeavor, it might seem realistic to put in long hours because it is a rewarding experience. But as things start to become a little more routine, the grind can take its toll.

Gigi’s advice is to “create within the parameters that you’re given at any moment,” explaining that content can be spontaneous and fun, not built in a lab day after day. 

You can see her mind spinning as she constantly considers how to turn any situation into a piece of content – even suggesting that her upcoming paper (she’s also working toward her Master’s degree, if this wasn’t enough) could be turned into a time-lapse to show her life as a student. 

Don’t get trapped doing the same things over and over; constantly expand your walls to take in more and more of your life, or try new ways to let your audience behind the curtain.

Spontaneity is not to be confused with lack of structure, however. One thing that every creator needs is a schedule or some set of guidelines to follow to make sure enough content is coming out. If that’s one post a week, that’s fine, but you can’t just hope that inspiration will strike often enough to build that following on its own. 

Getting paid

Everyone that is listening to Success Story wants to hear how someone got to where they are, but they also want to know how it makes money. Gigi was pretty open about how she has turned this into a full-time business, one that now sports eight employees. 

When I suggested that some people could try to do it as a side hustle, while they do something else full-time, she didn’t agree.

“I think the downfall of that is you might not take it seriously.” 

That answer shows exactly why she has come so far in such a short period. It wasn’t just a side hustle, she was all-in from day one and wouldn’t stop until she found success. While some people might still shrug and say “but I can’t,” that’s kind of her point. If you want to follow in her footsteps, there are no half-measures. 

They are willing to pay, you have to know what to ask

When discussing her negotiating strategy, that determination came flying out once again. 

“Throw a number out there. When somebody agrees to it, upcharge. The next time they agree to that higher number, okay, upcharge.”

It’s a good lesson for any budding creator that believes in the quality of their work. Fight for the price you want, and don’t back down just because it is a big brand. Ask them for their budget and work from there. If they don’t come close to your regular fee, tell them to come back to you in the future. 

“There’s no reason why I don’t deserve to be paid for the work that I do because it is really f—ing amazing.” Well said, Gigi, and something we all need to remember from time to time.

Final thoughts

There is so much more with Gigi that we can’t fit in this email. We spoke about topics like:

  • Her history with TikTok hashtag challenges
  • The scarcity mindset
  • Financial stress
  • Content cadence
  • Building a personal hierarchy
  • And many more

If you would like to watch the full interview, be sure to head over to the Success Story YouTube channel. 

Remember, find that next lilypad and just make the jump. Before you know it, you’ll be halfway across the pond. 

Thanks for joining me – I’ll be back with more Success Stories next week!


Success Story Podcast

If you like the content in this newsletter, I host a Top 10 Business podcast, (with over 20m downloads) called “Success Story”, where I interview entrepreneurs, executives and other high performing individuals so you can learn lessons and insights from the world-renowned leaders.

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