Career SkillsCareersLessons on Leadership

How to Succeed When You’re Feeling Boxed In

By Jacquelyn Adams

This week we are taking a walk down memory lane, all the way back to my 6th-grade year. So buckle up and get ready for a bumpy and awkward ride.

My school had an event that was the elementary version of prom. It was a really big deal. Everyone looked forward to getting dressed up and seeing who was voted as winners at the ceremony.

Or at least it felt like everyone was excited except me.

The 6th grade Jacquelyn was that stereotypically awkward, nerdy type… except so much worse. I was the same size as girls two or three grades younger than me, was perpetually the last person picked for any sports team, and “painfully shy” did not even begin to describe my disposition.

And it only felt like all of this was amplified when placed beside my older sister for comparison (which I felt like everyone did… constantly). Paula was two years older and had won an award at this event when she was in sixth grade because she was beautiful, outgoing, thoughtful, and genuinely engaging. As adults, she is a close friend who loves me fiercely and helps me grow, but at that time, I saw her as the person who set the bar that served as a clothesline to me.

As the day approached, I dreaded being held up for comparison one more time. I knew I had to come up with my own game plan for dealing with this ceremony in hopes of not falling short.


Assess the situation

The one thing that I had in my favor was that this engineer’s mind was already budding in that scrawny body. I knew I needed to put on my troubleshooting hat. I took a step back from my feelings and all of my disappointment. It was time to assess the situation. There are moments when we feel like there are no options. However, that is rarely a true reflection of reality. Maybe we don’t like the possibilities, but they are still available. Acknowledging these options can be empowering. There are also moments when we can see the vague options, but it is hard to flesh out exactly what they entail. Then it is our job to take the time to detangle them and figure out our course forward. I considered what possibilities lay before me. I could stay home, but that smacked of cowardice. I could go, knowing that I would feel defeated. Or I could go, but make it on my own terms.

Change the game

As a 6th grader, I didn’t understand the art of happy mediums. I refused to be held up to my sister for comparison once again. I decided to be the apple to her orange. So… instead of dressing up in my fancy clothing in preparation for this formal affair, I decided to dress like a boy. Honestly, I was a bit astounded by my genius and daring. I could not fail because she and I were playing entirely different games. This was the first time I took a stand to show my individuality, and if I was going to participate, I was writing my own rules to the game.

Know your allies

I was fortunate enough to have allies on the homefront and on the battlefield. My sweet, amazing momma did not quite understand what was going on in my 6th-grade mind and heart, but it was clear that, for me, it was an important battle that I needed to fight, even if it was only with myself. She did not even try to discourage me. She helped me acquire the tie and dress slacks from my cousin and tucked up my hair in a baseball cap to “hide” it. She did need to completely understand “why” I was going dressed up in disguise. She was in my corner regardless.


There was no fooling anyone into thinking I was actually a boy — again, when you’re shorter than girls who were three grades younger than you, this type of camouflage is impossible to pull off. It took my friends all of ten seconds to realize it was me. Looking back, one of the most surprising parts is that my friends had my back too. Sixth grade is an awkward time when being different can feel like a slow and painful death. However, instead of backing away slowly from the weird girl in the tie and cap, my friends thought it was awesome that I tried to trick them and laughed with me instead of at me. I had my allies and I had a great time.

There are times when I wonder how different things would have been if I hadn’t started making those small, seemingly insignificant stands that meant so much to me. Do I constantly play defense and struggle to live up to the external expectations that I feel have been put upon me? There are still plenty of times now where I need to give myself the reminder that I have options. And when it becomes a bit too much, I think of that younger version of myself and recall that I can choose to play a different game.

Jacquelyn Adams is a storyteller and an award-winning CEO. She lives in a world of constant exploration, whether it’s summiting Mount Kilimanjaro, vlogging about the future of work… or discovering how she’d do in a chocolate eating contest (answer: last place). Find more of her Lessons on Leadership articles here or connect with her on LinkedIn here.

Jacquelyn Adams

Jacquelyn Adams, founder and CEO of Ristole, uses her column to delve into the wild world of leadership. Whether the article is about her days as a Peace Corp volunteer, exploring corporate training, or even grabbing lunch at Chipotle — she will come out with a story and her “top tips.” As she passionately believes in leveraging her platform to share others’ voices, her column welcomes guest bloggers to create a fuller and more diverse pool of experiences for her readership. So, welcome to “Lessons on Leadership” where you never know what the next article will hold: online networking advice, guidelines for creating a joyful workplace, or even puppies. Just keep reading to discover what’s next!

Related Articles

Leave a Reply

Your email address will not be published.

Back to top button