There is something both exhilarating and humbling about becoming a beginner again.
You can be experienced, accomplished, and confident in your abilities and suddenly find yourself in a world where you’re the new person in the room.
That was me when I left the Getty Trust and joined PeopleSoft.
I wasn’t starting my career over. I was starting something new with everything I had learned so far.
The J. Paul Getty Trust’s multi-year ERP implementation came to an end. With the end of the project came a conversation I wasn’t expecting.
I was going back to my old job.
Closing the books. Managing the back-office team. Returning to the role I left to lead the implementation.
Strike one.
At the same time, my husband and I were planning to relocate 50 miles away for a better environment to raise our kids. I asked whether we could work out a modified schedule that would make the commute manageable.
My boss wasn’t willing to accommodate my request. Me starting an hour earlier and getting on the road by 4pm wasn’t reasonable to her. We lived in the LA Metro area, this would make a huge difference in my commute and not impact my team.
Strike two.
Then came strike three.
After successfully leading three major implementations, I wasn’t promoted. Instead, I was being asked to take on even more responsibility in my “old” role. No recognition of the work I was being asked to do being significantly changed.
I realized I had a choice: Accept the path that had been laid out for me or Create a different one.
I picked up the phone and called our PeopleSoft representative.
I asked if there were any openings.
He was ecstatic.
He told me he never approached a client about leaving their company, that just wasn’t something you did. But if I came to him, that was a completely different story.
Within a week, he made me an offer.
My new job was Account Manager, which was essentially what we now call a Customer Success Manager.
I would manage accounts in the Western Region.
There was one other important condition: I didn’t have to wear pantyhose.
Yes, you read that correctly.
It was a kind of a joke, but it was also a big deal to me at the time.
I had spent years in the Trust Office wearing suits, stockings, and corporate shoes. The idea that I could work for a software company and dress more casually felt like a pretty good deal.
I was in.
And then I got my first account.
It was an insurance company with a Big Six accounting firm leading their implementation.
It was the largest PeopleSoft sale the company had ever made.
When the sales representative first talked to me about the account, he was calling from his brand-new yacht.
I remember thinking, Okay… I guess software sales is a little different from General Accounting.
The project was enormous.
It was complex, large-scale, and involved multiple departments. And at the outset, I was the only PeopleSoft person associated with the account.
No large customer success organization. No army of specialists. No playbook.
Just me, the customer, the implementation team, and a lot to figure out.
And this was only one of my accounts.
I also had a large supermarket chain, a regional bank, and a restaurant chain.
Every one of them was a new experience.
It was my first major career shift in a long time, and I loved it.
I loved digging into new skills, new ways of working, and new people. I was learning how businesses worked in industries I knew very little about, while figuring out how to help them get value from software.
And it was different from working in the nonprofit world of the Getty.
There was much more focus on revenue and results. Decisions were less about “management by committee” and more about getting things done. The organization was more structured, and the pace and expectations were different.
It was energizing.
I had a few things going for me.
I loved the software. I had considerable functional and technical depth from my ERP implementation experience.
I was curious. I wanted to understand my customers’ businesses, not just their software problems.
I was customer-service oriented. I genuinely wanted my customers to be successful.
And I was super organized.
Those things turned out to be a pretty powerful combination.
But the bigger lesson was that changing careers meant being willing to become a beginner again.
I was successful in my previous career. I knew accounting. I knew ERP implementations. I was comfortable with what I knew.
Now I had to stretch.
And in those early years at PeopleSoft, I learned some lessons that have stayed with me throughout my career.
1. Build your network.
Meet as many people as possible. You never know when a relationship will become important.
Over the years, I’ve collected contacts, built relationships, and stayed connected with people from every chapter of my career. Sometimes you need an expert. Sometimes you need an introduction. Sometimes you need someone who has been through what you’re facing.
Having a network means you don’t have to figure everything out alone.
You can’t build it when you need it.
Build it along the way.
2. Be courageous.
At first, I wondered whether I should share my opinions with my customers about how they were approaching their systems.
Who was I to tell them what they should do?
Honestly, it was probably a confidence issue. Imposter syndrome wasn’t even a thing back then!
I checked my gut with more senior colleagues, and more often than not, they agreed with what I was thinking.
Eventually, I stopped second-guessing myself.
I kept asking deeper questions. I challenged assumptions. I made suggestions.
And something important happened.
My customers began to trust me, not just to support their software, but to tell them what I really thought.
Those became deep, trusting relationships.
3. Keep learning.
I was comfortable with the product, but I didn’t stop learning.
I kept taking classes. I read prolifically. I asked a lot of questions.
I wanted to understand not only what the technology could do, but what was happening in the industries and businesses of my customers.
The more I learned, the more valuable I became.
And I discovered something I still believe today:
Being good at something is not a reason to stop learning it. It’s a reason to go deeper.
4. Be organized.
Working with multiple customers means constant context switching.
You have to remember each customer’s priorities, what you promised to deliver, who the players are, what happened in the last meeting, and their story.
It is impossible to keep all of that in your head.
I developed my own techniques for staying organized and tracking my actions and theirs, managing contacts, capturing commitments, and keeping the context I needed for every customer.
The specific tools and techniques will be different for every role, but being consistent and intentional about how you organize yourself isn’t optional.
It is a career skill.
It became one of mine.
Looking back, I didn’t realize at the time that this seemingly simple change would become the beginning of my career for decades.
I thought I was leaving accounting.
What I was really doing was discovering a new version of myself.
I found that I loved customers. I loved technology. I loved solving problems. I loved learning about businesses.
And most of all, I loved the pace and possibility of the software industry.
That first career change opened a door I didn’t even know I was looking for.
And I walked through it.
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