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What is your biggest regret from your time in working in the business field and what would you have done differently?

I am going to pursue a degree in Business in college, but am not sure what specific business career I will thrive in/enjoy, so thought this would be a thought-provoking question to help me out!

business spring25 management business-management business-development women-in-business
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Juney’s Answer

Though not specific to my experience in business, and not regrets so much as learnings:
* I should have acknowledged that my career might not be the same from graduation to retirement, earlier.
* I should have asked more questions, and asked for help / a mentor, earlier.
* I should have focused on figuring out how to prioritise, earlier.

The world, industry and we are ever-changing, so having an open mind, humility & curiosity allows one to pivot. Over time, I acknowledged my own indefinite ignorance, and embraced asking folks with perspectives, backgrounds & experiences different from my own for their input. It broadens my view every single day, enabling me to fast follow and pivot in a VUCA environment.

With that, I'd say -- explore widely, keep asking excellent questions, and practice saying 'no' and 'not now' (to yourself as well as others)!
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Dan’s Answer

Hi Sydney,

There are two mistakes I've made across my 25 year career that I'd do differently.
First, be more open to putting yourself in uncomfortable situations or roles. Getting more experience across different disciplines will compound your business knowledge exceptionally faster than staying in one place for long periods of time.
Secondly, be deliberate about the career path you want to take. As you gain more experience within your career the path you enjoy/thrive at, will become more clear. Plot your moves in that path (like steps) in order work towards your destination by gaining the experiences you need to achieve the destination.
Lastly, don't get caught up in trying to find the perfect career....just start and the path will begin to present itself as you walk it.

Best of luck....look for opportunity....be deliberate in your moves.....and just start moving forward!
Dan
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Christina’s Answer

My biggest regret was being too self-limiting early on in my career. For example, I doubted that I was ready for a promotion because I didn't feel that I had enough time within my current role to even consider the next level. One day, a coworker who was not my mentor, but who was a respected leader in the organization, reached out to me and encouraged me to apply for a promotion to a position that my boss had recently vacated. I thought she was crazy at first, but I went for it and was quickly hired! The lesson was, don't put yourself in a box - just perform, and your career will start to carve its own path.

I work in the worksite benefits insurance industry, and we all joke that none of us set out to work in insurance, but here we are! I absolutely love my company and the people I work with are kind, smart, caring individuals. I'm so glad to have ended up here, but I never could have imagined it as a college student trying to chart out my future career. Best of luck to you as you discover your path!
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Charlie’s Answer

Sydney,
This is my favorite question so far.

My biggest regret is not taking more time to help members of my team realize their career goals and aspirations. Looking back, I spent way too much time focusing on myself and my own business goals. I managed one radio station group for fourteen years, looking back, what's most valuable to me are the relationships I still have with the people that I worked with years ago. I could have been a much better leader.

Always be willing to do whatever you ask others to do, if you're the manager don't stand by and supervise, roll up your sleeves and help with the dirty work. If you expect others to stay late, you stay late with them. If you assign someone to clean the bathroom, grab a mop and help out. I'm describing a different kind of leadership, one that leads by example and not "do as I say". Your managerial style will be groomed by those managers who do things well and more importantly by those you do not manage well.
In the end have no regrets.
Charlie
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Barbara’s Answer

Remember that everything is a learning path. What some may consider as a "mistake" or "regret", for others, any situation can be used for your advantage.

Constantly learning and connecting with others in your field can always helps. You will meet amazing people in your journey and in college that can teach you a lot.

My biggest "regret" is not believing enough in myself from the started.
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Brad’s Answer

I wish I had taken more communication courses in school. I learned by diving in, even though it made me anxious. It might have slowed my progress early on, but I still grew and advanced in my career later.
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Nneka’s Answer

Hi Sydney

One of the things I wish I had done more of was to attend more networking activities and being part of networks. Joining networks helps with career progression , knowledge exchange and mentorships. It provides access and visibility .

Good luck
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Nicole’s Answer

I regret not speaking up for myself at the start of my career. Having a mentor or coach back then could have helped me see what my career could be and what I wanted. Knowing more about career paths, preparing for promotions, and dealing with senior leaders might have advanced my career faster, with fewer changes and less stress.
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Paula’s Answer

Hi Sydney,

Thanks for asking this interesting question.

I wish I had realized how much change happens at work and how important it is to have a growth mindset instead of a fixed one. Believing in your ability to learn and pick up new skills will help you succeed through any changes at work.

Wishing you all the best on your learning journey!

Paula
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Cesar’s Answer

Always remember, you will discover your path.

Stay curious and open-minded, and you'll explore many opportunities in business. Looking back, I realized I worried too much about my next steps. You'll find more happiness by enjoying the journey rather than stressing over possible problems.

A wise person once told me that being too busy is like an illness. Take the time to pause and reflect on why you're doing things. This will help you become more successful and happier in your career.

Lastly, maintain a good balance between work and personal life. Without this balance, it's hard to go far.

I hope this advice helps you. I wish someone had shared it with me earlier.
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wendy’s Answer

When I think back to the early years of my career, I see all the times I didn't share my ideas and played it safe. I was scared of looking silly and was eager to be the “team player,” and I kept telling myself the timing wasn’t right. That quiet cost me—projects I could’ve led went to someone else, feedback I needed never got said out loud, and my path drifted instead of moving with intention. It hit me that silence is a decision too, a vote against my own potential, and no one can champion what they never hear. Since then, I’ve learned that a clear ask and a steady voice open doors faster than waiting for the perfect moment. I’m braver about naming what I want, owning the value I bring, and course-correcting early, and work finally feels like mine. If you’re where I was, don’t wait for permission—say the thing, make the ask, back yourself, and let your voice be the key that unlocks your next step.
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Michael’s Answer

My biggest regret is not taking advantage of buying into the business when the opportunity arose and thinking I was fine as a regional manager. I didñt let my dreams keep growing with the business. Build the business as if you own it and grow with it. The owners will appreciate it and reward you for it.
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Cassandra’s Answer

That's a fantastic question!

I only wish I had started earlier. I truly love my work, but I didn't realize this was a career option in high school or even college. I wish I had explored different business and finance paths and looked for internships sooner. So, I encourage you to seize any chance to connect, learn, or volunteer in the business field. Explore anything that interests you!
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Carlos’s Answer

I wish I had started my career in computing sooner. I spent 10 years in aviation mechanics, where I learned strategic and critical thinking. Eventually, I got the training and certifications to become an Industrial Engineering Technician, which opened up new opportunities for me. Here's what I learned and what I would do differently:

Lessons Learned:
- Strategic and Critical Thinking: Skills from aviation mechanics helped me transition to computing.
- Training and Certifications: Getting the right qualifications made my career shift successful.

What I Would Do Differently:
- Start Computing Sooner: Dive into computing earlier to take advantage of new technologies and career opportunities.

Tips for Starting Your Career Early:
1. Find Your Interests: Think about what you love and choose a career that matches your strengths.
2. Get Educated: Take courses and get certifications in your chosen field to build your skills.
3. Use Your Skills: Apply what you've learned in past jobs to new career paths.
4. Stay Updated: Keep up with industry trends to spot growth opportunities.
5. Network: Connect with professionals for advice and career guidance.

By following these tips, you can kickstart your career earlier and set yourself up for success in computing or any field you choose.
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