Early Career Lessons Learned – Product Management
8 min read

Early Career Lessons Learned – Product Management

With my 24th birthday approaching and a recent promotion on my resume, I’ve decided it’s time to share my early career learning’s with the world. Many people say that 24 isn’t old, but I disagree. It’s about five years older than when I started working and four years older than Mark Zuckerberg when he co-founded Facebook.


I was a pretty stereotypical ‘jock’ in high school with no clue what I wanted to do or work on when I grew up.  I played a lot of lacrosse and did a lot of partying with friends.  I was a sub-par student that did whatever I needed to do to get by, and I was content with that.  I always told my teachers, friends, and parents that I’d work hard in college but that there wasn’t a point in pushing myself in high school academics.  Now I disagree, and you will too after seeing the grammatical errors in this post, but that’s how I was at the time.

I went to Hobart College for my first year of college.  I chose Hobart because it was the only D1 school I was recruited to play lacrosse at, and luckily it had excellent academics.  Lacrosse went well besides several nagging injuries that persisted throughout the year.  More importantly, I did well in school.  I had a 3.0 avg GPA, which didn’t surprise me but shocked everyone from home.  I decided to transfer to Loyola College in Maryland in my sophomore year.  I knew I didn’t want to play lacrosse anymore because I didn’t feel that the time investment would pay off in the long run.  Also, Hobart (as great as the faculty was) was very liberal and didn’t have any majors that interested me.  At Loyola, I decided to major in MIS.  I had always liked technology and applying technology but never considered myself to be technical.  I knew CS wasn’t for me as I can hardly add or subtract without using my fingers.

I found myself with a lot of free time on my hands when I started at Loyola.  I was used to a very rigorous schedule at Hobart filled with lacrosse practice, gym time, and classes, but 2/3rds of that didn’t exist at Loyola.  During my second semester, my Intro to e-Commerce professor would announce internship and job opportunities before each class period.  One day, he read one that was for a company I had never heard of called Bill Me Later, said it was in Timonium MD and that they were looking for a Consumer Marketing intern.  If I remember the flyer correctly, I think it only said that they were looking for a student pursuing a CS or MIS degree who was willing to work hard.  Well, that was me.  I called up and interviewed with my soon to be bosses and ended up with the job.  I think I was selected over the other applicant solely because I said I lived in the area and was willing to work during holidays and summers.

Several years later, I find myself writing a blog post about the things I’ve learned, in a house that I recently purchased.  I was an intern for several years for Bill Me Later, which was bought by eBay/PayPal in late 2008.  I then became a part-time employee as I finished school since I was working 30+ hours/week with a full course load.  I then became a full-time employee as an “Associate Product Manager” and was recently promoted to “Product Manager.”


For you to truly understand what I’m saying, you…

  • You love who you work for… your bosses, your team, your company.
  • You’re passionate… about products you work on, and products in general.
  • Your career is young… <5 years in this field.
  • Your career is a major part of your life… it’s your other girlfriend.
  • You’re a product manager… you have a hard time defining your exact role.
  • You work on web products… everything is a product for you. Your product has products.
  • You’re not a genius… If you are then congrats, but I’m not, and I don’t work with any.

10 LESSONS LEARNED (in no particular order)

  1. You need a mentor, and you need to surround yourself with smart people who are willing to help you grow.  I was fortunate enough to have the same mentor, well, two mentors from the time I began working until very recently.  They have made a tremendous impact on my life, professionally and personally.  I genuinely believe they’ve made me a better person.  They are/were both the greatest teachers I’ve ever had in my life.  This is invaluable.  You need a mentor.  You also need to surround yourself with people who are smarter than you.  I never like being the most intelligent person in the room.  I’ve been fortunate enough to work with engineers who are both smart and caring.  They are willing to help me grow and fill the holes where I’m incapable of filling on my own.  This relationship is especially meaningful in product management because it encourages me to prescribe what we want but not in terms of how to do it.  Engineers are very creative, so let them use their creativity.  This is life… you need mentors.
  2. You may not always like what you’re doing, but you’re always learning, so deal with it.  As a product manager, you will spend a lot of time doing a lot of tasks that you fucking hate to do.  You won’t always like the projects you’re working on, and you won’t like finding and helping fix a recurring bug or process.  You may not like focusing on marketing plans or operational tasks, but you need to do them.  Product management is interesting and exciting because, in most organizations, your role is relatively undefined/broad.  In ours, you’re an athlete and are willing to play any position at any time if it’s what the coach calls for.  No ifs, and, or buts; just fucking do it.  You won’t like everything you do, but you deal with it because you’re passionate about your product and making it the best it can be.  Everything you do, whether you like it or not, is a learning experience that you’ll be grateful for later.  This is life… you’ll need to do shit you don’t enjoy.
  3. Your job boils down to making decisions and exercising good judgment.  I’m not aware of a product management school, major, or certification that will make you a good product manager.  It boils down to experiences and judgment.  If you have a good judgment (you either do or don’t) and can learn from your mistakes and other mistakes, then all you need is to add a lot of different experiences to your repertoire.  Accept mistakes and failures; learn from them.  You’ll get better with time.  This is life… a series of decisions resulting in experiences.
  4. Your career is a top priority.  You don’t have kids yet, and you aren’t married.  I have a long time/serious girlfriend, but that’s not the same as being married with kids.  My career is my baby.  Even if you don’t feel like you’re compensated fairly financially for the time you put in, you will learn twice as many [valuable] lessons than you would have by just working 9-5.  That in itself will pay off eventually if you’re in product management, then your hours aren’t for debate anyway.  You’ll inevitably need to help troubleshoot an unexpected production issue at 3 am on a Saturday.  There is no such thing as 9-5.  Your career is your life, so throw the concept of hours away.  Do what you need to learn all you can while you don’t have too many other priorities.  I firmly believe your loved ones and career should be where you focus >80% of your time.  As Mumford & Sons sings, “Where you invest your love, you invest your life.” Love your partner, and love your career.  This is life… invest in what you love.
  5. Welcome change, but don’t bank on it panning out as soon as you expect.  Sometimes important people (such as your mentor) leave unexpectedly, or a new hire comes on board.  Maybe your lead QA resource has a baby weeks earlier than expected to create a huge bottleneck.  Things happen.  From my experience, you’ll feel negative changes immediately and will need to make a lot of sacrifices and adjustments to counter them.  From my experience, good changes such as new employees joining or positive org modifications take a long time to make a positive impact.  It takes a long time to get people up to speed, no matter how great or experienced they are.  Have patience and do your best to transfer your knowledge.  This is life… unexpected events occur, and you need to face them head-on, with patience.
  6. Speak up when you need to speak up.  You’re smart, and you know when things are going awry.  Maybe your team is getting completely bombarded, and you can picture things exploding one month down the line. Perhaps somebody isn’t doing their job, and it’s creating a huge bottleneck. Maybe you’re unhappy and think you’re unfairly compensated.  No matter what it is, if you can prevent something wrong from happening or if you have a small fire inside that doesn’t go away for a while, speak up.  I pride myself on being the drama-free, low maintenance employee that managers pray for, but this has come to bite me in the ass a few times.  I’ve learned to speak up when needed, and it’s the only solution.  This is life… you shouldn’t keep everything bottled up inside.
  7. It is impossible to stick to a roadmap.  This one pains me to say, and I know many experienced product managers and visionaries will write me off, but try to hear me out… This isn’t impossible at a lot of companies, but it is for many others.  I won’t even say it’s impossible at our company, but from my personal experiences and the team I’m on, it is.  However, this is not such a bad thing.  I love that our team still behaves like a startup, even though we are a mature company.  Our team is just one group within it, and we’re undoubtedly one of the most nimble of all.  I love that we can quickly crank out code and implement a fix or feature within a short amount of time.  With this being said, our abilities and capabilities are sometimes abused, and we often get sidetracked, thus diverting from our “roadmap.”  This is life… you can’t roadmap your life and expect it to pan out exactly as planned.
  8. Have empathy for other groups in the organization.  Develop relationships with other groups (marketing, customer service, all IT groups, sales, etc.).  You’ll work with each of them at one time or another on projects, but it’s valuable going further than that to understand what each of them does every day.  What are their problems, and what are their goals?  The world doesn’t revolve around you or what you’re working on.  The entire organization is essential, and every employee matters. This is life… you need to recognize what’s going on with people around you.
  9. If you want to know if you’re eligible for a raise as an intern, then ask your boss; don’t go straight to HR.  This doesn’t make your boss look great, and when you love who you work with (as stated in the assumptions), you can talk to them about these things.  I’ll never forget this one.  This is life… it’s not smart to make somebody (who ultimately controls your salary) look bad.
  10. You’re only good if you’re a customer/user.  The best way to learn about a product is to use it, and use it a lot.  This is not going to help you think like most of your customers since most will only use the product a few times, or only once, but it will help you learn how your product works.  Nearly four months of my career was spent conducting UAT, supporting QA, and managing releases.  It sucked sometimes, but it was extremely valuable.  It kills me when I hear that he/she (an employee) does not have an account and has never used our product.  I want to scream and tell their manager to get their shit together.  You and everyone you work with needs to go further than to “think like a customer”; you need to be one.  Product managers don’t only work for a company; we work for our customers.  I think of myself as our product evangelist AND our user evangelist.  This is life… you won’t get too far being fake, and you can’t know what you don’t know.


I may only be nearing 24, but I’ve learned as many valuable lessons from 19-24 as I will during my career between 39-44.  Work your ass off and do whatever needs to be done to learn as much as you possibly can.  If you aren’t passionate about what you’re working on or who you’re working with, then stop wasting time and pursue your passions.  Surround yourself with smart people and work on things that can potentially reach millions of people.  This is life.