September 13, 2024
A few months ago, I left a startup company after working there for over three years (a lifetime in startup world), and only recently have I finally been able to put my reflections down on paper. During these few years, I had the privilege to witness and contribute to the growth of an incredible team, meeting and guiding everyone (except the 48 hires before me) through the hiring and onboarding processes. From the early days to the vibrant community they are now (150+ employees), it’s been a journey of growth, resilience, and learning. For me, two themes resonated with me throughout these years.
Giving Grace
One of the most valuable lessons I’ve learned during my time with this startup is the importance of giving grace — to others, and, perhaps most importantly, to myself. In a fast-moving startup, we all faced steep learning curves. Whether it was our first-time CEO navigating uncharted waters, first-time managers learning how to lead their teams, or veterans transitioning from military life into the private sector or startup space, each of us were learning how to navigate between complex work relationships and various mindsets. We had such a diverse group of people. Some were more mission-minded while others were more profit-minded. However, our diversity was our strength, and grace was the bridge that allowed us to support one another through our growing pains.
Perhaps the hardest part was learning to give grace to myself. There were many moments when I had to remind myself that it was okay to stumble, okay not to have all the answers right away (or at all), okay to just get started and not worry so about getting it perfect on the first, second, or even third try. I struggled with “good enough” for quite some time.
So what does self-grace look like in a start-up environment?
Acknowledge the learning curve. Recognize you are in a new role, with new challenges, and that it’s okay to make mistakes as you grow into the position. And most likely, you will be taking on multiple roles until your team grows as others take on some of the responsibilities you are carrying. And although 90% of startups fail or drastically pivot within their first couple years, they are wrought with learning opportunities for everyone involved.
Reflect, adjust, and move on. Don’t dwell on the mistakes, reflect on them AND adjust your approach THEN move forward. This may take some time especially if your new approach(es) need to show some results.
Finally, be self-aware and know when to ask for help. Seek advice from a mentor or peer who has been in a similar position and let them guide you through your growing pains. This was where I failed in the last 18 months, and it affected my physical and mental well-being. I saw this happen with a few teammates early on; however, I was not as aware of the significant impact it was having on my own health this past year. So for the last 3 months, I’ve been practicing self-compassion and grace – a gift I will carry with me far beyond this experience.
Being a Good Team Player
Another cornerstone of my startup experience has been striving to embody the virtues of a good team player, inspired by Patrick Lencioni’s book The Ideal Team Player. In my career, I’ve encountered various types of team dynamics, and Lencioni’s model of being humble, hungry, and smart resonated with me. In a startup, I saw firsthand how these virtues are not just ideal — they are essential.
- Humility taught me to listen more, to value everyone’s perspective, and to recognize that great ideas can come from anywhere.
- Hunger kept me motivated and driven, pushing myself and others to exceed expectations, and although we may have to settle for “good enough…for now” in implementing business processes and operations; we should never settle for “good enough” in our personal and leadership development.
- Being smart. In the context of Lencioni’s model, refers to emotional intelligence—understanding how to navigate relationships, connect with colleagues, and foster collaboration. These skills are indispensable in the high-paced, high-pressure startup environment.
My experiences in this startup not only refined these qualities in me, they taught me how crucial they are to building a successful team. I am so grateful to have grown alongside each and every one of them; they allowed me the opportunity to exemplify these values every day.
Cherishing the Journey
As I look back on the past 3 years, what stands out are not just the milestones we achieved as a startup, but the meaningful camaraderie and relationships and the challenges we overcame together. I am thankful for each of the people I met, and I was lucky to have met everyone in the company! Their part in my startup experience helped shape me both personally and professionally.
And while my startup chapter has now closed, I carry the lessons learned wherever the next step of my journey takes me. I will continue to push boundaries, and yet, remember to give grace to each other and to myself while being a humble, hungry, smart, ideal teammate. Here’s to new beginnings and to another incredible journey!
I leave you with this poem I wrote and sent on my last day to my closest teammates, who I worked with almost on a daily basis:
To my team that holds the line:
In the labyrinth of codes and cyber trails
Through onboarding trials and offboarding gales
You stood as guardians, strong and true
The best team I've known, I owe so much to you.
With every user logged and every system secured
Through endless updates and threats endured
You proved your mettle, your unwavering might
In the darkest hours, you brought forth light.
IT Ops and SecOps, a seamless dance
You made the impossible seem just a chance
No trial too daunting, no task too grand
Together we thrived, hand-in-hand.
As I step away, know this to be true
The company's in good hands, all thanks to you
Your skill, your passion, your unfaltering grace
Will carry on, even in my place.
Farewell, dear teammates, with gratitude profound
May your journey be smooth, your successes unbound
In every new challenge, in every bold stride
Know that I'll be cheering for you from the other side.
~ Doc Siders ~
Rebecca's iNSITE 
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