7 Career Lessons I Learned the Hard Way (So You Don’t Have To)
Practical wisdom for getting ahead without stumbling through the same mistakes.
Welcome to Career Field Guide—a newsletter for ambitious professionals who want to build meaningful careers with real momentum. I share actionable strategies and hard-earned lessons from my time at Amazon, Microsoft, and private equity-backed companies.
All articles are free to read—if something resonates, I’d be grateful if share it with someone who’d benefit.
I remember walking Microsoft’s campus as a new hire and feeling like the dog that finally caught the truck—I'd landed the prize, but had no idea what to do with it.
Starting a new job is exciting—but intimidating. I learned how to excel in the role through trial and error over the next couple of years.
These 7 lessons from my experience will help you skip the dumb tax I paid and set you up for a strong start.
1) Don’t wait to be told—get in the driver’s seat from Day One.
I’ve worked at Fortune 500 companies and startups with fewer than 10 people. One thing they all have in common? Problems. Everywhere. People are often shocked when I tell them that many billion-dollar companies still run their supply chains on Excel—even the ones that sell supply chain software.
I share that to make one point: there’s always something broken. Be a good listener, spot the cracks, and start fixing things.
You may not solve big problems on Day One—but you can take initiative. Take notes in meetings. Send out a clean summary with next steps, even if no one asked. It’s a small move that signals ownership—and most people don’t do it.
I’m constantly surprised by how many people say they want to grow, yet won’t lift a finger unless they’re told to. If you take on problems with a positive attitude, even imperfectly, most managers will notice—and appreciate you more than you know.
2) Be helpful, not impressive.
Early in your career, it’s tempting to try to sound smart, over-explain, or subtly flex. Don’t.
Most people (especially your manager) aren’t looking for someone impressive. They’re looking for someone helpful.
Show up prepared. Solve real problems. Follow through. Ask how you can support the team, not how you can stand out.
Ironically, the more helpful you are, the more impressive you become.
3) You don’t need to know everything—just be the fastest to learn.
In Mindset, psychologist Carol Dweck introduces a simple but powerful idea:
“If you take two people—one is a learn-it-all and the other is a know-it-all—the learn-it-all will always win in the long run, even if they start with less innate ability.”
I still struggle with this. As a type-A overachiever, I hate not having the answer. But pretending to know and being wrong is infinitely worse than admitting, “I’m not sure—I’ll find out.”
When you’re new, you have a window where every “stupid” question is fair game. Use it. Learn everything: how your company makes money, what leaders value, what happens upstream and downstream of your role.
Start by mastering your own team and function. Then branch out: book 1:1s with other teams, get curious, and learn fast because the fastest learner usually ends up the highest earner.
4) Your manager isn’t your teacher—they’re your customer.
A lot of early-career professionals expect a manager to act like a teacher: set the syllabus, spell out expectations, tell you exactly what success looks like. But that’s not their job.
As you level up in your career, you need to flip that script. Your manager isn’t your instructor—they’re your customer. That means your job is to understand what they value and deliver it consistently, with as little friction as possible.
Figure out how they operate. What do they hate? What do they praise? What earns their trust? Then design your workflow around making their life easier and their outcomes better.
Watch who they promote. Listen to who they respect. Learn what “great” looks like in their eyes and reverse-engineer it into your performance.
5) Understand the business, not just your role.
It’s expected that you understand your job—that’s table stakes. You should know your responsibilities, your metrics, and what success looks like. Don’t be like most people and stop there.
The people who grow fastest are the ones who understand the business—how it makes money, what drives value, and where the risks are.
I’ve sat in on executive discussions at Amazon, Microsoft, and PE-backed firms. What always stands out is how quickly leadership can rattle off financials, competitive threats, customer pain points, and upcoming initiatives. They don’t treat that knowledge as extra—they see it as essential.
If you want to be seen as a leader, act like one. Research your company’s performance. Learn what moves the stock price. Understand the sales engine, the cost structure, and the market dynamics. When you can connect your work to the bigger picture, leadership sees you as a partner, not just a contributor.
6) Develop a strong sense of self-awareness
Understanding how others perceive you—both the good and the bad—is one of the most underrated skills in the workplace.
For example: I know I’m often seen as a take-charge, hard-working leader. I also know that same intensity can make me come off as aloof, harsh, or even arrogant. Early in my career, I beat myself up over those flaws. Eventually I realized that this isn’t about fixing who I am, it’s about managing who I am.
At most companies, being perceived as a jerk will quietly kill your career no matter how smart or driven you are. That’s why I go out of my way to smile, ask people how they’re doing, and slow down to have real conversations. This does not come naturally to me but I do it because I’ve learned that I can seem abrasive if I’m not intentional.
You don’t have to be perfect but you do have to be aware. Start by listening when people give you feedback, especially the uncomfortable kind. Look for patterns in performance reviews and pay attention to how people respond to you in meetings. Self-awareness is not a personality trait. It's a skill you can develop and turn into a powerful advantage in your career.
7) Don’t fall in love with the job or the company. Fall in love with building a meaningful career.
I’ve been through layoffs at multiple companies and here’s the hard truth: the same company that asks for two weeks’ notice from you can give you a 15-minute meeting and two weeks’ severance.
That’s not bitterness—it’s realism.
You may love your new job, your coworkers, and the company’s mission. I hope you do. But don’t confuse the job with your identity. Companies come and go. Your health, your family, and your soul matter more than any logo on your LinkedIn.
A career is long and deeply personal. Define success for you.
Ask yourself early:
What am I willing to give up to succeed here?
How much time am I willing to trade for promotions?
What ethical lines am I unwilling to cross, no matter the reward?
I’ve had seasons where I worked weekends, skipped family events, and pushed harder than I should’ve. And I don’t regret the effort—it built my career. But I wish I had been clearer about what I was building toward.
Build a career you’re proud of—not just a job you’re excited about.
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