8 Lessons I Learned the Hard Way
Mistakes everyone (from intern to executive) should avoid in their career.
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8 Hard Lessons I’ve Learned on the Journey to Managing $450M+ in Projects
Filed under: Learning & Growth
A few months ago, I asked myself one simple question:
“What early career mistakes will I never make again?”
The result: 8 big mistakes that everyone—from interns to executives—should avoid in their career.
Let’s dive right in:
1. No Delegation
The mindset “If you want something done right, do it yourself” is a trap.
I learned the hard way that refusing to delegate only leads to burnout and missed opportunities.
Early in my career, I tried to do everything myself—every task, every decision—because I thought it was the only way to maintain control and ensure quality.
But by not delegating, I was stuck in the weeds, unable to lead effectively or develop my team. A hard lesson to learn.
Delegation is about choosing the right person, setting clear expectations, and providing the support they need. Check in regularly and hold them accountable.
That’s how you build a strong, capable team.
2. Ignoring Feedback
Before I got the hang of leading people and projects, I made some mistakes:
I dismissed feedback as criticism.
I believed my way was the best way.
I failed to see the value in others' perspectives.
Ignoring feedback cost me valuable insights and made me blind to better performance. It took me longer than it should have to realize how much constructive feedback could elevate my work and my team’s performance.
It’s not easy to seek out and accept feedback, especially when it stings, but learning to listen and reflect on it is what separates the good from the great.
Feedback isn’t a threat; it’s a tool for growth.
3. Sugarcoating Facts
I used to think that sparing people’s feelings by sugarcoating bad news was the right thing to do.
But I learned that honesty, even when it's tough, is crucial. During one project, I sugarcoated the reality of a looming deadline issue, thinking I was protecting the team from stress. When the truth eventually came out, trust was damaged, and rebuilding it took time.
Your team deserves the truth, no matter how hard it is to hear. Clear and honest communication allows them to respond effectively.
Honesty builds trust; sugarcoating destroys it.
4. Too Many Meetings
This was the hardest lesson to learn for three reasons:
Meetings can feel productive but rarely are.
They disrupt deep work and focus.
They can drain time without adding value.
I used to pack my schedule with meetings, thinking it was the best way to stay on top of everything. But I soon realized that most of these meetings were unnecessary. The key isn’t the number of meetings but their quality.
Now, I only hold meetings that have a clear purpose, well-prepared materials, groomed participants, and proper documentation.
5. Not Building Systems
Early on, I didn’t see the value in building systems. I thought a skilled team and clear goals were enough. But without strong systems in place, projects became chaotic, and we wasted time on redundant tasks.
Once I started implementing systems, everything became smoother—from communication to project execution. Systems act like guardrails, keeping your team on track without constant oversight.
Goals give direction and even push you forward in the short-term, but eventually a well-designed system will always win.
6. Transactional Relationships
I used to view relationships as purely transactional—what can this person do for me or the project?
But over time, I realized that the best relationships are built on trust, respect, and genuine interest in each other’s success. Transactional thinking may yield short-term gains but causes long-term losses.
Building real relationships creates a network of support that extends beyond any single project.
7. Keeping the plan in my head
I once kept the project plan in my head, thinking it made me indispensable. It only caused confusion and weakened the team.
In hindsight, I see this was disrespectful, unprofessional, and selfish.
Now, I make sure the plan is documented and visible to everyone—whether through collaboration tools, printed posters, or daily huddles. No excuses.
A shared plan is a successful plan.
8. Not Saying “No” Enough.
This one was tough.
I used to say “yes” to everything—every request, every additional task, thinking it was the best way to be a team player.
But I learned that saying “yes” to everything spreads you too thin and leads to mediocre results.
Learning to say “no” was about understanding my limits and prioritizing what truly matters. It requires a change in mindset: Identify your top priority (just one), and align your tasks with it. If something doesn’t align, cut it.
Prioritize what matters and let the rest go.
Takeaway: Avoid these mistakes to lead successful projects with confidence. Learn, grow, and keep pushing forward.
It's good to learn from your mistakes. It's better to learn from other people's mistakes. - Warren Buffet
Until next week,
Kyle Nitchen
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The trouble is I keep learning and then repeating the same mistakes. Any advice on getting out of that loop? LOL.
Nice list. I think 3, 4, and 6 are closely related and probably source back to lack of confidence in our PM training or communication training. Good post.