A PMP Reflects on Milestones

If an interviewer asked me to describe my experience with milestones, I would say:

“I am a milestones professional. I have:

-??????Created milestone forecasts

-??????Reported on progress toward milestones

-??????Presented milestones to broad and various audiences

-??????Adapted/adjusted milestones

-??????Managed milestones

-??????Failed to achieve milestones, when required in the interest of the business

-??????And Achieved milestones within the originally forecast window”

I know milestones. I am not new to milestones.

What I am not an expert in, though, is how curiously and unpredictably milestones can evoke feelings. Sometimes the experience of achieving milestones, is not always what we imagined it would be.

There was a project I worked on in which I was both personally and professionally invested. I wanted this project to be successful because I earnestly and passionately believed it was the right thing to do for the business at the time. I worked on this project for almost two years, seeing it through from crazy idea, to business proposal, to the Sales and purchase process, to design, to implementation, to pilot, and finally to GA launch.

For launch day, I had traveled to be on site for the all-hands meeting where the project would be officially delivered company-wide. In addition to the months of work and thought invested in the project itself, I had prepared personally for this launch day by shopping for just the right business outfit (with company colors represented), had my hair cut and colored, purchased new make-up, and practiced my remarks in front a mirror. The live-streamed broadcast went (almost) flawlessly. The screen share was great until my kids texted me one minute into my remarks with a horrible, joking selfie I had taken earlier that morning. There was a riot of laughter when that photo popped up on my screen from my kids. It turned out to be a good thing, though, it helped me laugh at myself and broke the tension I was feeling.

After the livestream was done, I sat down in the office with my new, fancy dashboard, and watched the usage numbers climb on the project throughout the day, and all was well. At quitting time, I trundled out of the office, and got some drive-through dinner on the way back to the hotel. I sat down at the hotel-room desk, unwrapped my burger, squirted out a pile of ketchup, and flipped open my laptop to take a screen capture of the day’s dashboard progress. As I did so, I started crying.

“What are you crying for? You just accomplished something huge! This has been two years of your life getting to this point! You should be happy, ecstatic even, joyful! What’s this all about?”

A note to people managers: when your staff achieve a big milestone, take the time to check on them. They may not be okay. Don’t assume they are happy, proud, or savoring the moment of their apparent success. They may not feel that way, at all. I wish a manager had taken me to dinner that night, and asked open-ended questions.

Some people report feeling a sense of satisfaction and accomplishment when they close out long-term goals. Some people feel like the goal is still unfinished, even after launch. When you move into execution the project may not be over for them, so they don’t stop and mark the moment or feel a sense of finality. They just pass into the next phase of the lifecycle without pause. This will set them up for burnout.

Me? I’m a goal-oriented person. I am “driven” (as so many of my managers have called me). I always have to have this sense of clear direction. Where am I going next? What has to get done next? What is needful now? So, when we hit that GA day, I was shattered by this sense of “So what do I do now that I have handed this project off to operations? What do I do next?” I felt slightly lost, and rudderless. I did not feel relief or freedom or a sense of accomplishment. I felt a sense of panic, and wondering where I was headed.

In the long-term, that project failed. It ultimately failed stakeholder acceptance. That is a mistake I have not repeated. I err on the side of being an over communicator now, so that every stakeholder I work with today gets to have their say at every milestone along the way. That project failure was one of my most powerful learning experiences. That project lives in my professional experience every day of my career. For me, it was a successful failure.

I am eight days away from another major milestone. This milestone was 18 years in the making. My first child is graduating high school. We had planned and intended this milestone for almost two decades, but suddenly being here is bringing back memories of that hotel room hamburger being seasoned by my tears. I had not expected to feel this way, as I watch my daughter accept her diploma. There is this curious mixture of pride in her accomplishments, and a sense of panic as she steps into her next education phase in college. As her mother, I have this sense of, “So what do I do now? What does parenting an early adult look like? What is it going to feel like setting the table for three instead of four 87 days now?”

I am drawing on being a “milestone professional” in this moment. I am reminding myself that this is a new phase for my “family project,” and that this is okay when the education phase passes to operations, and this is normal. I am taking time for retrospection, and for metacognition. I am observing my thoughts, and making sure I am both in and of the moment. I am a milestones professional. I know how to do this.

To the high school #classof2022 : welcome to LinkedIn! Welcome to this first day of your professional lives. We are here to support you, listen, mentor, collaborate with, and celebrate your successes. Let me tell you about milestones…Sometimes milestones are not what we expected them to be...