What the Mentality of the Dotcom Era Can Teach the AI Generations


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The mentality of the dotcom era of the late 1990s and early 2000s was all about hard work, grit and a willingness to prove ourselves. It was such an exciting time, and it didn’t matter what company we worked for; we just wanted to be part of the movement. And it was a movement — a period marked by extreme growth and the spirit of the possible. We wore many hats and didn’t care about job titles. We learned a vast amount of knowledge while learning and growing on the job.

In the last few years, however, I have seen a shift in mentality among the newest entrants to the workforce — many expect to walk straight into their ideal position from college. This generation is much farther ahead than we were because the technology pioneered in those days has long been embedded in our business practices. While important, this advantage alone will not set them up for success.

For those building their career, brand or business, marrying the mentality of the dotcom era with today’s intelligence tools will take you further and faster than was possible in any previous era. Now is the chance to get organized, invest in yourself and build for the long term.

Related: How to Lead a Multigenerational Workforce

Find ‘instant’ gratification through hard work

The expectation of instant gratification is understandable. Today, you can order something from Amazon and receive it the same day. Short-form video has replaced long-form copy. Everything is fast, fast, fast. But there’s a productive way to get that sense of instant gratification in a business environment. How? By leaning into the dotcom mentality and setting milestones for yourself.

This is exactly what I did throughout my career. Even if I was pushing myself and taking on additional projects, I’d always set a goal for myself. It could be getting a project to the point where I could pitch it. Or coming up with data to show how to best execute the idea. Setting milestones can give you that sense of instant gratification constantly — on a daily, weekly, or monthly basis.

At some point, as you mark off those milestones, you will also need to articulate your plans to your audience. Often, people take the initiative in the background, so provide context and storytelling around what you are doing to bring it to the foreground. That is important, whether it’s during a one-on-one with your manager or if you are trying to scale up to lead a team. If everyone buys into your ideas, you will gain more gratification — and though the feeling may be instant, it will be built on careful planning and hard work.

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Shape your career through self-investment

A lot of people from the dot-com era are today’s tech leaders. It’s the old metaphor about pressure building diamonds — working across roles, experimenting, and innovating forged our characters and careers. But what I have seen more recently is people letting their employer shape their destiny. As individuals, we need to take more control over our careers and understand the results won’t come all at once.

Expecting a role even before you have proved worthy of it is working backward. It took me eight to 10 years of doing the work of a CMO before I actually got the title last year. Instead, give yourself the grace to shape and mold yourself first. Take on extra projects and get involved, even if you are a small fish in a big project. The key is to get your foot in the door. Once you have mastered one skill or responsibility, you can take on the next.

That means being willing to fail, picking yourself up, and then validating the learnings. I’ve been there, done that. Very rarely do my emotions go up and down these days — because I managed the most difficult situations as I grew into the role of CMO. I can assure you that going through the trials and tribulations will make you feel super confident when you finally land the role.

Embrace feedback as a gift

While the modern worker may feel empowered by rewards, in the dot-com era, just being part of the movement was seen as reward enough. Marrying the two mentalities comes back to setting your mind to receive feedback as a gift, no matter how it is delivered.

Being open to feedback demonstrates that you’re humble and want to grow. Eventually, the gift of feedback will bring you full circle so you move from receiving it with grace to giving it with grace. Making it clear you want to learn by actively asking others for feedback will encourage them to provide it and help you improve.

When switching roles, there is an art to delivering feedback. If you read the room right, people will start to see your value and hear your voice. How you give and receive feedback is the most important factor in bringing back the best elements of the dot-com era: It shows we are all in this together and you are invested in the success of our shared ideas and goals.

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The future of work today

The latest arrivals to the workforce are not so far removed from the people who proved themselves in the dot-com era. Culture is the big through line because nobody wants to work in a silo. In fact, eight of the 10 people I interviewed recently expressed they were looking forward to coming back to the office to resume in-person collaboration.

The traits I want to see in a candidate are the same ones that define the dot-com mentality. I want self-starters who are hungry and have that grit and hard work in them — the type of people who will manage their manager. When we marry that mentality with how advanced the talent is today, the workforce is only going to get better and stronger. And just like in the dot-com era, there will be no telling what we can create together.

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