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From Analog to Digital: My Journey as an Elder Millennial

Updated: Mar 6

Hi, I'm Rebecca Leppard, and I am proud to be an elder millennial. Born in 1983, I am in the generation that properly functions with and without the Internet.

As we navigated the transition from analog to digital, we acquired unique skills and experiences that set us apart from our younger and older peers.

I graduated from university in 2006, just as Facebook was becoming popular among college students. At that time, we still used flip phones and desktop computers, and Google was not yet the ubiquitous search engine that it is today.

For my research dissertation, I had to go to the library and look for information in physical books and journals. It was a time-consuming process, but it taught me the value of patience, perseverance, and critical thinking.

After graduation, I landed a job as an editor in a national magazine. I was thrilled to have the opportunity to write and edit articles for a living. It was indeed the dream job for any fresh graduate of journalism school. I put my head down and worked like a dog.

At the age of 24, I was promoted to senior editor, making me the youngest person to hold that position in that magazine's history. Oh, I was given a 20% salary raise too, so I felt fabulous. While it was a huge accomplishment, it came with its own set of challenges because my direct reports were at least 5 years older than me and had been in the industry longer than I had.

I had to earn their respect and trust, which took time and effort. I also had to learn how to manage people, delegate tasks, and provide feedback in a constructive way.

In 2009, I decided to make a career change and transitioned to the public relations (PR) industry. I moved to a different city where I knew nobody and didn't speak the local language. It was a risky move, but I was ready for a new challenge. I started as an account manager, working with clients from the hospitality and tourism industries, which were brand new to me. It was a steep learning curve, but I enjoyed my lifestyle. It was in Bali so I could not complain much, really!

Within six months, I was promoted to account director. By the time I was 27, I was leading an entire PR agency, managing multiple accounts simultaneously. I had to juggle different responsibilities, such as developing PR strategies, pitching stories to journalists, managing budgets, and mentoring junior staff. It was a demanding but rewarding job because it felt like I earned a Master’s degree in marketing communications while getting paid!

One day I was sent to Singapore for a business trip and there I met with who would be my husband to this day. Yes, I met him in real life (IRL) and immediately “swipe right”. We started our relationship with a handshake, nerves and all and these days, we get on each other’s nerves. A whole 180 degrees, right?

In April 2013, I became a mother and two months later I landed a new corner-office job in a 5-star hotel. It was a big change from working at a PR agency, as I was now responsible for managing the hotel's reputation, media relations, and events. I had to collaborate with different departments, such as finance, kitchen, operations, and HR to ensure that our messaging was consistent and effective.

It was also a big change from being a working woman to a working mother. I never had to consider hard-stopping a meeting to pump my breasts for the baby I left at home. I once had to run out of a conference room because I was leaking through my bra, blouse and blazer!

Then I experienced another novelty when I was pregnant with my second child. This was the first time I was a pregnant worker in a luxury hospitality environment. That means the grooming standards were expected. Also, I must practise restraint with scrumptious sashimi and free alcohol around me day in and day out.

After almost 5 years in that coveted office, I had to ask myself whether I wanted to stay there till I retire or get out of my comfort zone and venture out into the unknown.

I think you know the answer to that question.

I took the plunge to a scale-up proptech company and became the direct report to the CEO. It was a risky move, as tech companies are known for their instability and unpredictability. My horizon opened up immediately. Every single thing, from the culture, and the tools to the crowd I meet is new and exciting. I was learning again. Yes!

From that tech company, I jumped to yet another demanding job: a consulting company. Of course, by this point, you know me well enough that I never take the safest route. Hello, steep learning curve, it’s me, Rebecca!

Fast forward to the year, we all remember - 2020. My husband and I made a tough decision and it’s not about circumcision. (Sorry, I just found the rhyme funny) Yes, we moved from Indonesia to ol’ England. From one tough place to live to another. I say that because I wanted to point out that moving to the First World meant we were adopting a brand new lifestyle and that lifestyle is called the “new poor”.

If you’re familiar with the term “new money” what we are now is the complete opposite. Leaving my homeland means we left behind the support system and the affordability of almost everything. But we moved to the UK to gain the security of education and healthcare systems for our children. Did I mention that we have three children now?

After a year of being a resident, I finally got the right to work in the UK and job hunting in the middle of the pandemic was fantastic. Just kidding. It was not.

But I was reminded of the many challenges in the job market as a woman, a person of colour, a mother, and an immigrant from a developing country. That was when I decided to found my own company. I call it Upgrading Women. I took inspiration from the many times iOS forced me to upgrade the software until I had to upgrade the hardware too. Capitalism, right?

Today, I am a mentor, coach, trainer, author, and speaker, sharing my knowledge and expertise with women in tech and beyond. I help professionals navigate the complex and competitive world using communication skills and strategy as tools.

In the many, many types of personal and professional conversations, everybody says, “The most important thing is communication.” And I am here to help with putting the action into words.

Yes, communication is important, crucial even. Actual planes have crashed because of intercultural communication breakdowns. I’m not kidding this time. Read what Malcolm Gladwell said about Asiana’s plane crash here later.

To end with something optimistic, I can see from Google's trend report how many people seek communication training and coaching. It can only mean that people are doing something about it: upskilling and building a strategy.

I am excited to see what the future holds for me and for my generation, who according to John Mayer, has been waiting for the world to change. Let’s not wait around. Let’s run the world. I am