3 answers
David
Student
Grove City, Pennsylvania
1
Question
Updated
162 views
What's the hardest thing you've had to do over the course of your entire career? How did you overcome the challenge?
Anyone can answer my question but I'm interested to see what the mechanics think of this question. It'd be cool to hear the answers and it may help someone in the future too.
Login to comment
3 answers
Nick Kelson
IT Manager
1
Answer
South Euclid, Ohio
Updated
Nick’s Answer
I’ll share two responses that represent some of the hardest things I have had to do in the dual careers that I have. I have been working in Information Technology for 25 years, and in addition to my day career, I also serve as the full-time Pastor of a church in my hometown, which is about an hour away from where I currently reside.
From an Information Technology perspective, one of the hardest things that I have had to do is learn how to work and be productive with very ambiguous information. Early in my career, I worked in Incident and Problem Management, focusing on issues where our software or site was not functioning as expected for anywhere from a single user to all users. There were times when the initial details provided were very vague, or I did not have the ability to see firsthand what was being experienced. In those moments, it was important not to show frustration, but to put myself in the customer’s shoes to understand how to best serve them and collect the information needed to get them back up and running.
Imagine asking someone on the phone to describe what they see and still not being presented with the full picture, or having to provide instructions with limited ability to know whether those instructions were followed. This early experience helped me learn how to listen better and shift my communication to fit the needs of a particular customer. It also positioned me to gain comfort with being uncomfortable for later aspects of my career. For example, when working as a project manager, there were times when requirements were limited, or when we engaged with vendors or third parties and visibility or clarity was not there. Pulling from those earlier days and learning how to work through discomfort helped me navigate those waters.
As a Pastor, the hardest thing that I had to do was step in as the full-time Pastor. This is the church that I attended from birth, and everyone there knew me before I knew myself. The main pressure point was the prior Pastor, who was my mentor and had been in place for 50 years. This person was a role model for me and was an icon well known in the community, having served in and led many community groups. Those were big shoes to fill, and here I was stepping in to fill his role when he retired.
Now I’m trying to teach folks who taught me, folks who have heard every possible sermon, folks who had sat in on more lessons and had more life experiences than me, and folks who saw me as that kid in church and now had to view me in a different light. I leaned on two pieces of advice that were given to me. The first was to just be myself. I leaned on this first piece of advice so that I would not try to duplicate someone else’s style or approach. I leveraged my own style for delivery and used an approach to community engagement and planning that aligned with my strengths and family structure. This really helped me establish my identity and find a flow that worked for me.
The second piece of advice was provided by the former Pastor’s wife. She gave me a poem that really spoke to how I was feeling. The poem spoke about a young Pastor stepping in for a well-respected Pastor and provided me with comfort. That comfort came from both the poem and the reassurance from the Pastor’s wife that they, she and her husband, had full trust in me and were there to support me as needed. Staying true to yourself and having folks in your corner who support you are vital to any career undertaking.
From an Information Technology perspective, one of the hardest things that I have had to do is learn how to work and be productive with very ambiguous information. Early in my career, I worked in Incident and Problem Management, focusing on issues where our software or site was not functioning as expected for anywhere from a single user to all users. There were times when the initial details provided were very vague, or I did not have the ability to see firsthand what was being experienced. In those moments, it was important not to show frustration, but to put myself in the customer’s shoes to understand how to best serve them and collect the information needed to get them back up and running.
Imagine asking someone on the phone to describe what they see and still not being presented with the full picture, or having to provide instructions with limited ability to know whether those instructions were followed. This early experience helped me learn how to listen better and shift my communication to fit the needs of a particular customer. It also positioned me to gain comfort with being uncomfortable for later aspects of my career. For example, when working as a project manager, there were times when requirements were limited, or when we engaged with vendors or third parties and visibility or clarity was not there. Pulling from those earlier days and learning how to work through discomfort helped me navigate those waters.
As a Pastor, the hardest thing that I had to do was step in as the full-time Pastor. This is the church that I attended from birth, and everyone there knew me before I knew myself. The main pressure point was the prior Pastor, who was my mentor and had been in place for 50 years. This person was a role model for me and was an icon well known in the community, having served in and led many community groups. Those were big shoes to fill, and here I was stepping in to fill his role when he retired.
Now I’m trying to teach folks who taught me, folks who have heard every possible sermon, folks who had sat in on more lessons and had more life experiences than me, and folks who saw me as that kid in church and now had to view me in a different light. I leaned on two pieces of advice that were given to me. The first was to just be myself. I leaned on this first piece of advice so that I would not try to duplicate someone else’s style or approach. I leveraged my own style for delivery and used an approach to community engagement and planning that aligned with my strengths and family structure. This really helped me establish my identity and find a flow that worked for me.
The second piece of advice was provided by the former Pastor’s wife. She gave me a poem that really spoke to how I was feeling. The poem spoke about a young Pastor stepping in for a well-respected Pastor and provided me with comfort. That comfort came from both the poem and the reassurance from the Pastor’s wife that they, she and her husband, had full trust in me and were there to support me as needed. Staying true to yourself and having folks in your corner who support you are vital to any career undertaking.
Alexander Figueroa
Technical Support Manager
13
Answers
San José, Costa Rica
Updated
Alexander’s Answer
I can actually answer this in two different ways. emotionally and logistically.
Emotionally, the hardest thing was letting people go.
Sometimes you can do everything right and still not get the result you want. Even when you don’t want to be the person making that call, there are moments where it’s necessary for the team or the project to move forward. I handled that by being as honest and respectful as possible, and by understanding that leadership sometimes means making difficult decisions, not just popular ones.
Logistically, one of the hardest things I’ve done was working with TECHO to build over 90 emergency houses in a single weekend.
We had to coordinate volunteers from across Central America, secure donations, organize materials, plan transportation, and make sure everything, from tools to food to emergency kits, was ready.
Our goal was to complete everything in about little over three days, and while we faced challenges along the way, we still managed to build over 90 homes. That experience taught me what’s possible when people are aligned around a purpose and willing to put in the work.
Whether it’s handling tough decisions or managing complex projects, I’ve learned to stay focused, adapt quickly, and keep moving forward, even when things don’t go as planned.
Emotionally, the hardest thing was letting people go.
Sometimes you can do everything right and still not get the result you want. Even when you don’t want to be the person making that call, there are moments where it’s necessary for the team or the project to move forward. I handled that by being as honest and respectful as possible, and by understanding that leadership sometimes means making difficult decisions, not just popular ones.
Logistically, one of the hardest things I’ve done was working with TECHO to build over 90 emergency houses in a single weekend.
We had to coordinate volunteers from across Central America, secure donations, organize materials, plan transportation, and make sure everything, from tools to food to emergency kits, was ready.
Our goal was to complete everything in about little over three days, and while we faced challenges along the way, we still managed to build over 90 homes. That experience taught me what’s possible when people are aligned around a purpose and willing to put in the work.
Whether it’s handling tough decisions or managing complex projects, I’ve learned to stay focused, adapt quickly, and keep moving forward, even when things don’t go as planned.
Carla Flores
Strategy Planning
5
Answers
Guadalajara
Updated
Carla’s Answer
One of the hardest things I’ve had to navigate in my career has been learning how to perform and stay consistent while living with Fibromyalgia.
It’s not just physical pain. It’s fatigue, brain fog, and unpredictability. There were days when even basic tasks felt overwhelming, yet I still had responsibilities, expectations, and goals I cared deeply about. At one point, I had to face the reality that I couldn’t keep pushing the same way I always had.
What helped me overcome it wasn’t “pushing harder,” but learning to work differently. I became much more intentional with my energy; prioritizing what truly mattered, building structure into my days, and being disciplined about rest without guilt. I also had to develop resilience in a different way: mentally. Showing up consistently, even if it didn’t look perfect, became a win.
Over time, this experience actually made me stronger. It taught me adaptability, empathy, and how to lead and perform under less-than-ideal circumstances. It also shifted my mindset from perfection to sustainability, which in the long run has made me more effective.
So while it’s been one of the toughest challenges, it’s also been one of the most defining in how I approach both my work and life today.
It’s not just physical pain. It’s fatigue, brain fog, and unpredictability. There were days when even basic tasks felt overwhelming, yet I still had responsibilities, expectations, and goals I cared deeply about. At one point, I had to face the reality that I couldn’t keep pushing the same way I always had.
What helped me overcome it wasn’t “pushing harder,” but learning to work differently. I became much more intentional with my energy; prioritizing what truly mattered, building structure into my days, and being disciplined about rest without guilt. I also had to develop resilience in a different way: mentally. Showing up consistently, even if it didn’t look perfect, became a win.
Over time, this experience actually made me stronger. It taught me adaptability, empathy, and how to lead and perform under less-than-ideal circumstances. It also shifted my mindset from perfection to sustainability, which in the long run has made me more effective.
So while it’s been one of the toughest challenges, it’s also been one of the most defining in how I approach both my work and life today.