Skip to content

Choosing My First Job – One of the Best Decisions of My Life

choosing my first job - paying off my houseDo you remember when you graduated from college? Did you experience that pivotal moment where you could have had fun in your work vs. getting serious and actually start adulting? I did, and when I reflect back on those moments, I consider choosing my first job to be one of the best decisions I’ve ever made!

Choosing My First Job – One of the Best Decisions of My Life

When I was 20 years old, I was on the fast track to becoming one of America’s best future engineers. I understood the math, I was getting mostly A’s in all my classes, and I knew that it was a career that would pay me well throughout my adult life.

Then, after completing an internship in my junior year, I realized that I hated it… I liked the math and physics behind engineering, but I wasn’t a huge fan of actually getting my hands dirty and proving out the concepts. Call me a priss, call me a mama’s boy…but I just didn’t like the practical application. After much thought about my talents and my passions, I decided to switch majors…from engineering to finance!

The Downturn That Killed My Beginning

In May of 2008, I graduated with a BBA in Finance. Hooray for me! But there was just one little problem…the Great Recession… Bear Sterns had filed for bankruptcy just the month prior, and in September, Fannie Mae and Freddie Mac, the Lehman Brothers, Merrill Lynch, and many other fine financial institutions went bankrupt as well.

My finance degree and I…we were screwed.

I was fresh out of college, I had absolutely no real-world finance experience, and most of the jobs I was looking for were being eliminated…not created.

The Job Search

The Michigan job market absolutely sucked, so I decided to travel down to Florida with my buddy who already had a teaching job (and an apartment) lined up. I planned on living with him, splitting rent, and possibly returning home if I didn’t find anything after 3-4 months.

Here’s a quick summary of my job search in Florida:

  • I arrived there in late July. The heat and humidity were so bad, it was almost like a literal punch in the face every time I went outside.
  • In the first month, I walked the streets of downtown Boynton Beach, walking into banks, telling them I was interested in interviewing. I nearly got one interview, but it never happened… There were just dead-ends all over the place.
  • I followed a lead from my wealthy contact from back home. It also went nowhere when they found out I had no accounting experience.
  • Per some coaxing from my girlfriend, I even applied to become a model. Turns out, being 6’8″ isn’t a plus for modeling (or I was just too ugly and they didn’t want to tell me that…) 😉

Three months went by and I still had no job.

My bank account went from about $3,000 to $300 and my daily cuisine of peanut butter and jelly sandwiches were starting to taste like soap. It was about time that I hang up this dream and just head back home to mommy and daddy.

…But that’s when the scales finally tipped in my favor.

From Nothing to Too Many Options

One day I had no job offers and no prospects, and the next I had two to choose from (isn’t this how life always works?)

Here were my choices:

  1. The Breakers Resort was interested in hiring me to work as part of their golf staff (I had 7 years of experience before heading down to Florida). They pay was $13 an hour, but there was talk of $100 tips from random members AND Jack Nicklaus lived nearby and would occasionally visit the course and play. This was my chance to meet a legend!
  2. Office Depot Headquarters extended an offer for me to work as a pricing specialist (which basically meant I would proof catalog pricing before it was mailed out to small business owners). The pay was $16 an hour.

I figured that it would take $12 an hour for me to survive in my Boynton Beach apartment, so both of these options met that criteria. Choosing my first job was suddenly upon me…

The golf job would pay $3 less, but after tips and yearly bonuses, I figured I could earn at least $16 an hour if not more! Plus, I could earn money by being out on the golf course! What could be better than that?

On the flip side, the Office Depot job would get me into Corporate America…and ultimately closer to my passion of finance. It wouldn’t be all that exciting, but if I worked hard and proved myself in the entry level job, I might just be able to climb the ranks and get into a high-paying finance role.

It might seem silly now…but choosing my first job was (at that time) one of the most difficult decisions of my life!

choosing my first job - speakingChoosing My First Job – The Selection That Changed My Life

While working (and playing occasionally) on the golf course was tempting, I thankfully was wise enough – even at that young age – to choose the pricing specialist job at Office Depot.

Since then, I’ve been promoted 5 times.

Here has been my path up the ladder:

  • Pricing specialist
  • Merchandising analyst
  • Cost Modeler (for a different company)
  • Associate financial analyst
  • Financial analyst
  • Senior financial analyst

Related: How to Get Promoted 5 Times in 7 Years

Life Today vs. What It Probably Would Have Become

Today, I’m a Senior Financial Analyst and the Finance lead for one of the top business segments of our company. I get to think up new lines that might do well in the market, present a business case for those ideas, and then help the team get that actual product out into the market. It’s an amazing job and I couldn’t think of anything that I’d rather be doing today!

So what would life be life if I took the golf course job?

  • I’d likely be an okay golfer, but definitely not pro (I was never that good)
  • If I stuck with the golfing industry, I’d have to travel between northern and southern U.S., depending on the season – six months in each place. Not ideal for getting married and starting a family…
  • If I weren’t in the golfing industry, I’d probably be floundering at some other job. A finance degree with no practical application for 5+ years is basically like no degree at all.
  • I’d be lucky to earn $20 an hour in whatever path I chose vs. WAY MORE than that by taking the corporate route.

In short, when it came to choosing my first job, I’m so glad I had the brains to follow the corporate path. It wasn’t easy or fun at first, but it gave me a great base to develop as a person, as a professional, and as a future leader in business.

Related: Top 10 Cities to Grow Wealthy in the United States

What Has Been YOUR Pivotal Moment?

Choosing my first job set me up for success in life and I can’t thank my “young-20’s self” enough for doing what was wise vs. doing what sounded the most fun in the moment.

We all have moments like this in our lives, don’t we? Every few years, we’re bound to hit a fork in the road. Either we turn left or we turn right – sometimes it’s difficult to know what the wise answer is at the time, and there’s no way to choose both.

Sometimes we’ll choose the wise path like I did 10 years ago. Other times we’ll reflect back on our decisions with a puzzled look on our face…asking ourselves something like, “How was I such an idiot? What made me think that that was a good idea back then?”

If you’re left shaking your head about your past, you have two possible options today:

  1. Either dwell on your mistake, play it over and over again as you explain why you can’t get ahead to your friends and neighbors…and then stay broke forever, or
  2. You can counter that poor decision from your past with multiple wise decisions today. Don’t use the past as a crutch. Learn, grow, and be better than the old you!

How to Make the Wise Decisions

At the time you’re presented with two options, both of them might seem equivalent (like they did for me between the golf job and the corporate job). Let me tell you though, they’re not. No two jobs are alike and one of them ultimately has a greater end result than the other.

So how can you know?

First, ask yourself what it is that you really want to do long-term. If I wanted to be a professional golfer or a head pro at a golf course, then the golf job would have made sense. But…I really had no desire to do either of those. Long-term, it made the most sense for me to pursue my passion in finance, and to do that, the best course of action was entering Corporate America. The job wasn’t in finance, but at least it got me one step closer to where I wanted to be.

Second, find some people that are actually doing the jobs that you’re being presented. Do they like them? Do they look back on their decision from 20 years ago and smile? Or are they telling you to run??!

Finally, seek counsel from other wise individuals. They might not know your industry, but they’re probably well-rounded enough and know you well enough to give some great advice on your situation.

After doing these things, you should have a clearer understanding about which option is best for you.

Sow what’s YOUR story? Have you ever had these pivotal points in your life?

Related: 10 Ideas for Wise Decision Making

Tell us all about it in the comments below! What was YOUR pivotal moment??

Battle of the Mind Money


My name is Derek, and I have my Bachelors Degree in Finance from Grand Valley State University. After graduation, I was not able to find a job that fully utilized my degree, but I still had a passion for Finance! So, I decided to focus my passion in the stock market. I studied Cash Flows, Balance Sheets, and Income Statements, put some money into the market and saw a good return on my investment. As satisfying as this was, I still felt that something was missing. I have a passion for Finance, but I also have a passion for people. If you have a willingness to learn, I will continue to teach.


  1. pretty awesome story. who knows how long you would have stuck with the golf job, something tells me you would have transitioned out promptly, but none the less, it is awesome to see you made a great choice then and your satisfaction today proves that.

    • It’s one of those things where you say, “I’ll just take this job until I can find the next one” ….and then 5 years later you look up and you’re basically screwed for life with no career track.

      So glad I took the office job!

  2. Glad that things turned out so well for you after such a rocky start. I thought you might have gone with the golf job simply for the contacts – so many businessmen golf regularly, and I wondered if you’d considered the contacts in the Finance area you might have made had you chosen the other path. Nonetheless, everything happens for a reason, and hindsight is always 20/20! 🙂

    • I actually had a job at a golf course for 7 years before that and had contacts from the members to get a job…it didn’t pan out. I wasn’t going to make that same mistake twice!!

  3. That’s a great story! Thanks for sharing it. I had a hard time finding a job I liked after college. It was frustrating, but ultimately led me to start my own business, which is something I never would have had the courage to do without some major frustrations from jobs.

Comments are closed for this article!

Related posts