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Why I was told not to become a Product Manager... and became one anyway

Dana Calderone

I always wanted to be a Product Manager. The role checks off all my desired career boxes: cross-functional and high-impact work, autonomy, responsibility, and continuous learning. On this path, I attended workshops, read product management books, listened to industry podcasts, and spoke to countless PMs. One PM told me, “If you think you want to become a PM, I would seriously ask you to consider why, because it’s not an enjoyable job.”

I became one, anyway.

Now, I’m a Growth Product Manager at Shortcut, and I’m here to tell you: it can be an enjoyable job if you’re in the right environment.

What’s Behind the “Product Management Isn’t Enjoyable” Myth

Contrary to many articles, the biggest challenges Product Managers face are rarely the technical expertise, product roadmapping, and sprint planning. All of these skills can be learned. The real reasons I’ve seen Product Managers become dispirited and leave their roles are the emotional and interpersonal aspects. Let’s consider these.

It Can be a High-Pressure Job

While some people like to think Silicon Valley employees are overpaid millennials with nap rooms, the reality is, our daily work consists of fighting to make our companies successful. (Then naps may be taken.) Startups have lofty growth targets and business stakeholders often want new feature launches and massive changes to the product under tight deadlines. An immense amount of pressure can fall on a Product Manager to make all of this happen, and any delay in the timeline can put the entire business at risk.

It’s Emotionally Taxing
Every day Product Managers make dozens of decisions, both small and large. Not everyone in an organization will always agree with these decisions. As a result, Product Managers navigate tense situations on a regular basis. Meanwhile, continuous pressure to deliver results, unexpected issues with development, and the near-constant juggling of high priorities tends to wear on Product Managers over time.

You’re Often the Bearer of Bad News
I’ve yet to meet a Product Manager who has too many resources. There is almost always more work being requested than can actually be done, considering the various constraints the development team may be under. As such, Product Managers have to make tough decisions on priorities. This means that PMs have the job of letting stakeholders know that their particular request is being deprioritized. These can be challenging conversations to have.

But You Need to Stay on Everyone’s “Good Side”
The job of a Product Manager is highly cross-functional. In addition to being the gatekeeper of resources and the bearer of bad news, you must simultaneously maintain positive relationships with all stakeholders, even when you’re pushing back on their requests.

Finding the Joy in Product Management: What it’s Like at Shortcut

High Stakes, But Everyone Shares Responsibility
Product Managers at Shortcut have a lot of responsibility. We make sure our customers are heard, that we’re moving in the right direction, and that we build high-quality and valuable products. However, at Shortcut, this is the whole team’s responsibility. We all share in the outcomes of each feature release, and we all share in the company’s success. Additionally, Product Managers at Shortcut work very closely with our counterparts in design and engineering. This means that from idea to delivery, every feature is a true collaboration. Shouldering the responsibility of outcomes together makes being a Product Manager feel far less burdensome and lonely.

A Proper Work-Life Balance Makes Both Work and Life Less Emotionally Taxing

We have high aspirations for the future of Shortcut, but we also balance our drive with rest. Work/life balance is a genuine priority for all employees at Shortcut. As in, people actually take their PTO. While we do move fast, having the assurance that we can rest when we need to means burnout at Shortcut is far less likely.

With Transparency, There is Less Bad News
Transparency is not only one of our core values, it is something we truly embrace. If you saw our internal slack, you’d see that almost all channels are public. That’s because we believe that everyone in the organization should have access to all the information around decision-making.

We also use this product called Shortcut (hey, that’s us!) to keep record of communications on prioritization and solutioning. Because of this, there are fewer surprises for stakeholders, which means fewer tough conversations, and everyone can follow along on the decision making that went into the work we prioritize as a company.

Staying on Everyone’s “Good Side”: Good People Make this Easy
Shortcut is full of good people with good sides. Another of our core values is to treat people right. We really take this seriously. If ever there is a disagreement on a decision, we work to find a path forward that everyone is comfortable with.

While we do work hard, we also make time for getting to know one another on a personal level (which is important, since we are a remote company). Maintaining good relationships is easy when everyone across the company is prioritizing empathy and kindness.

It’s Rewarding

While Product Management has its challenges, it is also incredibly rewarding. Nurturing a product from an idea to something that touches users, brings them joy, and makes their lives easier is incredibly fulfilling. So, even when the emotional and interpersonal challenges of Product Management feel daunting, delivering good products to the world that do good things makes it all feel worthwhile.

In the right work environment, and with the right tools, product management can be a joy. Even for those product managers out there who are actually fed up with product management.

If this sounds like you, check out our recent job openings, or see for yourself how Shortcut works and get started for free.