From Discouraged and Confused to Thriving in my Career

Jared Orr
5 min readSep 29, 2022


It was December 2017. I walked across the stage, shook some hands, and received my bachelor’s degree in Business Management. I had the world at my fingertips. Anything was possible!

The only issue? I wasn’t that great of a college student.

Yes, by the grace of God I had the degree, but I also had a 2.7 GPA and very few marketable skills.

But that’s okay. I had a job lined up! A sales job at a company of which I was very familiar with. I had been using their product for a few years at that point so I felt confident that I could close lots of deals, make lots of money, and retire before the age of 30. Nothing could stand in my way!

I started the job in January of 2018 and was out by the end of June.

Here’s what happened:

The company itself was pretty awesome. Big office in the heart of downtown Scottsdale, Arizona, 8 fully stoked kitchens, pool and foosball tables galore, fun music playing, and a mostly-casual work environment. Every millennials dream, am I right?

While all of that was nice, the job itself sucked.

Yes, I was fully aware that I would be making cold calls. I was ready for that. But I didn’t realize that this sales job was basically telemarketing. And get this, every single person in the offer (with the exception of IT and HR) were either making telemarketing calls all day or managing a team of people making telemarketing calls all day.

I realized very quickly that this was not a good long-term place for me. Also, I sucked at the job so that helped me get the heck out of dodge as quickly as possible.

So there I was, a miserable telemarketer and recent college grad with no marketable skills looking to make a career change. But what else was there besides sales?? I literally had no idea what type of career I wanted to move into.

So I did what anyone in my situation would do and just started applying for jobs in LinkedIn and Indeed. And let me tell you, the range of the jobs I applied to was as wide as Agent Smith’s mouth.

I applied for positions like onboarding specialist and recruiter, and also applied to be a plumber. I had zero plumbing experience but I was so desperate to get out of my current role, I was willing to learn anything.

After about a month of applying for everything and anything, I came across a job title that I hadn’t heard of: Customer Success Manager.

“Ohh sounds fancy” I thought to myself. I did some more digging into what this job title actually entailed and long story short, I decided to narrow down my search to Customer Success jobs since I knew without a doubt that this was the perfect career path for me.

If you’ve made it this far and don’t really know what a Customer Success Manager is, take a minute to watch this video.

After about another month of searching, I was able to score some interviews! I made it to the final round of interviews for a CSM role at a social media marketing company just up the street from where I was working. The interview was in-person and it was at 9am. I had to be at work at 8am so I lied to my boss about needing to come in late for some reason. I honestly don’t even remember the excuse but to this day, it’s the best lie I ever told.

Needless to say, I aced to the interview, got the job offer, and put in my two weeks. When I told my boss about the new job offer that I accepted, she told me that if I quit this job, I will quit everything else for the rest of my life.

PSA: If your boss tries to manipulate and guilt you into staying in a role that you’re miserable at, don’t do what I did by putting your two weeks in. Walk out immediately and never look back.

This was June of 2018. It’s now September 2022.

So where am I now?

I work as an Enterprise Customer Success Manager for a Customer Success software platform. I have been invited to speak on multiple podcasts and webinars. I have become a six figure earner. I have created a large network of other Customer Success professionals. If it wasn't for my network, I wouldn't be anywhere close to where I am today.

Bust most importantly, I’m thriving in my career.

I love my job. I love what I do. I love the community I’m apart of and am so grateful for the relationships I’ve built along the way.

Just a quick synopsis of my career since my first CSM job: I worked in that role for over a year. I then got a new CSM role at a global software company. This was a remote role and I worked with teammates from all over the world. I even got to travel to Europe to meet most of my colleagues. After over 2 years at that job, I got my first senior-level role at an IT company based out of NYC. I knew one of the directors at this company so she helped me get this role. After almost a year there, I was unfortunately laid off.

But, thanks to my incredible network, I was able to find a new senior-level role in less than a month! I even got a pay raise so it all worked out.

Your network is your net worth. I’m living proof of that.

Again, there’s no way on God’s green earth that I would be where I am today in my career if it wasn’t for the friendships I built over the last 2–3 years. Through networking, joining online communities, creating my own content through LinkedIn posts, blogs, and podcasts, I was able to not only grow in my professional abilities but be prepared to bounce back quickly from an unexpected layoff.

Over the past year, I have spoken with nearly 100 people who want to make a change in their career. While most of my conversations have been with people who want to move into Customer Success, I have been the designated hype man for anyone who is wanting to thrive their careers.

Does the situation you’re in sound a lot like mine back in 2018?

If that’s the case, I’m glad you’re here. Connect with me on LinkedIn and introduce yourself. I would love to connect.



Jared Orr

I want to help as many people as I can thrive in their career!