5 Lessons I’ve Learned as an Over 50 Influencer

June 23, 2023

How Becoming a Social Media Creator Helped Me Find My Passion & Redefine My Career Goals

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I'm Jen!

I'm an over 50,
former Corporate America
9 to 5-er who walked away from a 25 year career in sales leadership to pursue my passion of coaching women to be their boldest and most confident self


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I really hate the word “influencer.” I don’t often use it to describe myself. 

I prefer “Enthusiastic Over-Sharer,” but I guess influencer rolls off the tongue easier.

My origin story as an influencer dates back to the spring of 2020 during COVID lockdown, and if you’d like to read it, you can click here: https://glossedworld.com/making-up-for-glossed-time

But today, I’m going to tell you about my journey through a different lens. How social media–a medium I once thought was full of only narcissists and bad dance moves–helped me see myself and my career path in a different light. How sharing my creativity, my experience, and my story online helped me find my passions and my purpose again. About “going viral” and what that really means. And how the biggest lessons I have learned from being a creator on social media apply to life, work and the internet.

I didn’t set out to become an influencer. It started as a self-imposed career challenge. At the time, I was working as an Account Executive for one of the largest luxury beauty and fragrance brands in the world. I knew social media would play a key role in how my teams sold to their clients post-COVID, so I thought I’d better learn how this whole Instagram thing worked. So, during lockdown in the spring of 2020, I started studying the platform and creating some content. I posted about what I knew–makeup, style, confidence–and geared it toward women over 40. I look back now at those posts and I cringe–terrible lighting, too loud background music, poor editing–but I wanted my teams to be able to see that if their 49 year old boss could put herself out there and try, that they could do the same.

Much to my surprise, I actually LOVED creating online content. It was tapping into my 3 superpowers–creativity, coaching and connection. I was connecting with women all over the globe– coaching them to try new things and teaching them new techniques. I would get messages from them–with pictures of an outfit inspired by one of my posts, with a close up of their makeup after watching one of my tutorials. I’d get questions about products, asked for my advice on what to wear or where to shop, and my opinion on a challenge they were facing. But what really blew me away were the “love notes” – messages about how I was making them feel about themselves that went WAY beyond the clothes and the makeup. Some said they had felt they had lost their spark and were finding it again. Others said they were feeling sexy and vibrant for the first time in years. There were stories of renewed confidence–of quitting jobs to pursue their passions, of leaving partners who made them feel unappreciated and lonely. It was then that I realized my bigger purpose–I was impacting their self love. I was becoming a confidence coach. And for the first time in my 25 year career, I knew what I wanted to do for the rest of my life. I needed to keep going. THEY needed me to keep going.

In the fall of 2021, I had my first viral video moment. And the funny part? I almost didn’t post it.

It was a lip sync to an audio that talked about being bad bitches and rallied for people to “come with me, there’s fuckery to spread.” I loved the message and the idea of it cracked me up. But, I questioned posting it. What would people think at work? Would some of my community find it offensive? Would I lose followers because of it? It was then that I made a critical decision for my brand–I was going to stay true to myself and show up as my most authentic version. And, well, my authentic version likes the F word. So I posted it. A couple months later, that clip had over a million views and my community ballooned to 30,000. Apparently, there are lots of people who like the F word, too.

By the summer of 2022, I was leading an online community of over 100,000 over multiple social media platforms. I knew I had found my calling, and in the spring of 2023, I walked away from corporate America to start my own business as a confidence coach for women over 40. At 51 years old, I gave up the 401K and the pension to chase down some new dreams in my second half. It’s a huge risk, I know, but I believed it was a risk worth taking.

So, what have I learned along the way?


I know, you’ve heard this before. I can feel the eye rolls from here. But hear me out.

This is not just on Instagram–I mean EVERYWHERE. And I know that seems like an obvious piece of advice, but here’s why: when you show up as your true self–flaws, vulnerabilities, fears, fuck ups and all–you protect yourself from burnout. We’ve all had friendships that started when we were “trying out” a version of ourselves that wasn’t quite us. We’ve had romantic relationships where we felt we had to operate at a certain level and hide our vulnerabilities. We’ve worked at jobs that tried to push our square peg selves into round holes. Showing up as anything less than your TRUE self puts you at risk for burnout–for a moment when somewhere in the middle of it all, you look around and ask yourself, “how did I get here and who is this person in the mirror?” I decided, back when I posted that first viral video, that if I was going to build anything online it would be built with a foundation of authenticity. Better to have 100 people that love you for exactly who you are than 1,000 people that admire a version of you that you have to “put on” over and over. When you start off any relationship as your truest self, you attract people who will accept all the facets of you.


I’m a GenXer. The generation of Big Wheels, typewriters and those stupid paddles with the ball attached to them with a rubber band. We did not grow up with technology. I didn’t know what a hashtag was when I started this. I freaked when I did my first Instagram Live and sweated out of my armpits. I didn’t know how to edit a video, how to create a YouTube channel or how fun doing a TikTok trend could be. But, I learned. I asked questions, I looked to those who were doing what I wanted to do and asked for their guidance and advice. You are NEVER too old to learn something new…and sometimes you’ll have to ask someone a lot younger than you to teach you. It’s humbling, but it’s OK if you don’t have the answers. One day you will, and then you can pass on your new found wisdom to others.


Want a good laugh? Scroll down to the bottom of my Instagram and watch some of my early videos. Back when I was too self conscious to film anything without music in the background, when I edited the videos with the exposure so high I looked like a lightbulb. They are cringe-worthy, to be sure. But, they remind me–and others–of how far I’ve come, so I leave them there. Social media–and life– can have you in a constant state of comparison paralysis. There will be those around you that seem to have it all together, that have more experience, that look better. STOP LOOKING AT THEM. You are not them. You are YOU. People follow people that they like, that they connect with, that aren’t afraid to be un-perfect. Three years after my first video from my bedroom, I still film the majority of my content there–with the laundry on the floor, a random drawer open in the background, the bed unmade. Sometimes the light is dim…and sometimes MY light is dim..but my human-ness has brought me more success and raving fans than my attempts at perfection ever have. I mean, if you really think about it, the most interesting people aren’t the “perfect” ones–they are raw, real, vulnerable, questioning, asking for advice, open to suggestion. Perfect is elusive…and boring as hell. Give me the flawed any day.


In my three years on social media, I have had a few viral videos of a million views or more. NOT ONE OF THEM took any longer than a few minutes to make. And here’s where Lesson 1 and Lesson 3 converge. In each case, it was me, being ridiculous–either lip-syncing to a funny audio or another where I said nothing at all and pointed to text. I POINTED and it went viral. It wasn’t a video of me running in a field in a dress with a 20 foot train, or a slickly edited compilation of video clips from a month in France. I stood in one place, delivered my message and hit post. But it was the MESSAGE that made it go viral. The humor, the relatability, the honesty…THAT’S what makes people like, save and share. I’ve had many other pieces of content that I spent HOURS filming and editing that I was SURE would go viral. And crickets. So, my apologies if you thought I would have the secret formula for virality here…the truth is I had no frigging idea when I had magic in my camera roll. But I will say this…a viral video is like chum in the water–you may get a fish on your line, but it’s up to you to get them in the boat. Thankfully, when I did get a viral moment and it brought people to my account, they saw more of the same when they got there. My viral content is no different than the posts with an average number of views. I’m ridiculous, real and myself always. The viral videos were the amuse-bouche for the 10 course meal of shamelessness and honesty that is me. So, don’t chase “trends”…just be yourself, have fun, and you’ll get the community you’re after.


Becoming a social media creator requires a thick skin. There are a lot of unhappy people in the world who will be more than happy to come and shit on your parade. I’ve had my share of rude, mean, judgmental comments that have made me pause and have hurt my feelings. People get real brazen when they’re anonymous—I’ve had some say I have a big forehead, that I should get my teeth fixed, that I have a gut (thanks, menopause), that they hate my hair. I’ve been condemned for my “unladylike” swearing. And don’t get them started on Birkenstocks–who knew THEY were so polarizing?? 

When I met my first trolls in my comments, I felt my Jersey girl coming out and my knee jerk reaction was to cut them back with words. But, I’ve realized that the energy you put out will ultimately be the energy you get back. So, I respond with empathy and kindness. Or I block their ass, which is also very satisfying. It’s a lesson for life–you will not be liked by everyone. Not all will find you attractive, brilliant, hysterical and magnetic. Your charms will not land with some. Just as in life, not everyone will be your fan. There will be those who are jealous of you, and minimize your accomplishments. Your job in life and on social media is to stop trying to be something for everyone. It’s impossible. Go back to Lesson 1. Start there and stay there. Authenticity will be the shield that protects you when a troll hurls a rock at your big forehead.

So, here I sit, almost 52 years old, embarking on a career path I never saw coming. I never thought social media would be a place that would pull together all the things I love to do. I didn’t know that Instagram would show me how much I had to offer. I was unaware that I had the answers to my midlife crisis in the palm of my hand. But, a few years later, I’m both scared shitless and vibrating with excitement about what my second half of life will look like. It’s been fun to dream again, to have that feeling I had back in the early 90s when I walked out of college and into a life of opportunity. That’s the sense I have now–that big things are on the horizon, that my purpose is revealing itself to me. This crazy ride has slapped me in the face and given me the biggest lesson of all: there is no expiration date on dreams, and you’re never too old to start dreaming again.

So, open that coffee shop, go full time with your art, sign up for those classes you’ve always want to take. We’ve got one life. Don’t let yours stop at 50.

What dreams have you kept on a shelf? Tell me about them in the comments.

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  1. Rogan says:

    I absolutely LOVED this post. I didn’t know you had a blog. I had to comment. I love what you are doing and you seem to be genuinely having fun. As a fellow blogger, I can absolutely relate to many of thr things you said…especially when it comes ro
    dealing with online trolls. Many times, they are just jealous. They want what you have and want to be doing what you’re doing. But, because they don’t know how to accomplish those things, they instead choose to tear others down. Keep pushing, girl. I’m so proud of you!

    • Jennifer Robinson says:

      Thank you, Rogan! It’s always those who’d never do the thing that criticize others who do. 🙂

  2. Maribeth Meyers says:

    You influence me every time I watch a reel, sit in on a Saturday or Sunday morning get-together, or read something on your blog. I going to be 70 on 9/8, and I went with my sister yesterday to get fitted for a “good” pair of walking shoes. Since April, I’ve lost 24 lbs. I still have a long way to go, but now I have the proper footwear to go walking. I even wear a bit more makeup than normal. When I lose more, I’ll follow your fashion and wardrobe tips. So what I’m saying is you teach out and help others start to find and expand out confidence in ourself. I wish I lived next door to you. I’m encouraged to be the ME I am working to be, thanks to you, Jen.

    • Jennifer Robinson says:

      Maribeth! 🥹
      These messages always hit me right in the feels. I LOVE that what I’m doing hear resonates with you and helps you see yourself in a beautiful light.
      I’m so blessed to have you in my community. 🥰

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