'That Could Have Gone Better' - Career Failure Reflections

Before I knew it, I had a mad dash to finish some critical projects at home and for work and at the end of the year and some of the posts I’d planned didn’t make it into this LinkedIn ether. I, like many, had begun reflecting on a year-end recap post that would include what I was most proud of accomplishing in 2024, but after attending a leadership development program in early December, I wanted to go a different route. The concept I think is still relevant and likely helpful for others as everyone finalizes their goals for 2025, was a reflection on my more recent career failures.

I’m being intentional in using the word failure and talking about what didn’t work, because as leaders, it’s important to show that failure is inevitable and necessary for growth.

After you read my lessons, if you want to walk in vulnerability with me, I’d love to hear what didn’t work for you and how you’re changing that this year in the comments.?

1. Dressing for the Job I Had, Not the Job I Wanted - When I first started my career, I dressed like the senior members of our team and leadership. I literally had the same outfits as people on my team –ultimately I’d begin to shop for work clothes out of town so that this would not happen given how small the retail selection was in our city. Then, like now, my appearance was important because I represented our company and being underdressed and possibly overlooked by the leaders I needed to engage with was unacceptable. However, anyone who works in tech can tell you how relaxed the dress code is for most organizations, mine included. When I worked in the office, I never went fully casual, but as time went on, particularly with remote work during the pandemic, I became more relaxed with my attire. In 2021, I decided I would introduce more formality to my appearance for any external engagement. This meant, taking extra time to put on makeup and collared shirts for meetings and presentations. As we returned to in-person events, I opted to follow the actual dress code suggestions for each conference, rather than defaulting to tech standards. In the last few months, I’ve made a more conscious effort every day. My intention behind these steps are to remove any doubts about my leadership abilities and credibility that could come from those who do use physical appearance as a measure for qualification.?

2. Being too discrete About My Career Aspirations - I had a few instances last year where people questioned my career interests and aspirations. One truth teller who questioned me, was clear that by not sharing what I wanted, it prevented others from helping me surface those opportunities. Both in theory and practically, I knew the value of sharing your career interests because it’s one of the main things I ask my colleagues and mentees, so that I can help them. But, I hadn’t thought about why it was important to do that for myself. As a result, I’ll be more intentional about having meaningful conversations with strategic partners who can help me explore and investigate the things that I’m passionate about doing in the future.?

3. Delaying Progress due to Perception Management - I’m a recovering perfectionist and while in the last few years I have adopted a “done is better than perfect” approach to my work, when it comes to passion projects –including these LinkedIn posts, I have a number of ideas that don’t come to fruition because I place a high value on making sure what I share feels genuine and not self-serving. However, my therapist helped me see that over time and as people interact with me and my writing, those qualities will be evident because they are natural and there will be a historical record of my patterns and intentions. One of my goals this year is to publish more content so I will focus less on trying to “get it” or “make it” sound “right,” and just let it touch whomever it needs to.?

There are more failures that I've acquired along the years, but I am sharing these three because they are critical for me to see improvement as I look to increase my impact on purpose-based projects.

All the best to you each of you reading this post as you reflect and set your intentions for 2025.