How To Become the CEO of Your Life with David 'DJ' Oragui

"What if I changed how I ran my 1:1s..."
"What if I changed how I coached my team..."
"What if I changed how I dealt with imposter syndrome..."
"What if..."
These are two of the most powerful words in leadership...
My guest this week lives by the philosophy that everything can be tested if we ask the question "what if..."
Listen in to my inspiring conversation with David 'DJ' Oragui, Director of Strategic Projects & GTM at Oyster®
In this episode...

0:25 - DJ's background -
DJ explains his role at Oyster®.
4:21 - First leadership position - A lot of DJ's leadership skills were self-taught.
7:54 - Digital marketing apprentice - DJ explains what he learned in this role.
10:36 - Left without a manager - What happened after DJ's manager decided to leave him in charge of everything?
13:18 - Succeeding as an apprentice - What key things allowed DJ to be successful in this environment?
14:48 - Behaving like a CEO - DJ expands on what this concept means.
19:03 - Passion projects - DJ explains the array of passion projects he's run over the past decade.
24:25 - The parallels of testing - What do testing ideas and managing people have in common?
30:26 - David's advice to himself - What advice would David give his younger self?

Connect with David 'DJ' Oragui:

Learn more about Oyster at

Learn more about your own leadership style at:

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How important is it to become the CEO of your life?

Why do you have to become one?

In this episode, DJ talks about the positive impacts of being the CEO of your life based on his own experiences.

Keep reading to know more.

DJ's background

David 'DJ' Oragui is the Director of Strategic Projects & GTM at Oyster®, a company that allows HR and software companies to hire people globally.

They help companies hire, manage, and take care of their global workforce through the Oyster®'s platform.

First leadership position

A lot of DJ's leadership skills were self-taught.

Even before he became a digital marketing apprentice in 2014, he already had three years' worth of marketing experience. He learned how to register the domain name and set up WordPress all by himself back in the day. And from doing that, he also started learning how to create content. As he was doing content marketing, he stumbled across SEO and paid acquisition.

DJ has always been naturally curious. He always had the desire to try and learn new things. He wants to explore and see what he's capable of. He wants to find out what his limit is. And so he continues pushing and learning new things, wherever it may take him.

Digital marketing apprentice

When DJ joined a marketing consultancy firm as an apprentice, he was responsible for writing blog content which he taught himself how to do. Eventually, he got promoted to a content marketing manager to manage the entire blog and their email nurture campaigns.

The very first articles that he wrote for the firm at the time were about how to find open-source images for your blog and how to use YouTube to grow your business. And in less than three months after those articles were published and the SEO was done, they became the most popular articles for that business.

Eight years later, the articles are still the highest performing content on the site.

Left without a manager

DJ shares that when he was at that marketing firm, his manager went away for a month and left him in charge of everything.

So what happened after his manager decided to leave him for a month?

DJ took charge of all the tasks his manager left him. He took over for the team and the firm when his boss was away for a month. He checked all the workbooks they had for all the tasks his manager was doing which helped him see exactly how to run a marketing consultancy firm.

A couple of months later, he was asked to be the Head of Content. However, at that moment, he was set to leave London and move to the north of England. He could no longer work in the office. But his boss offered him to work remotely.

And so, Dj agreed to continue working for them as he had always wanted to work remotely.

Succeeding as an apprentice

What are the key things that allowed DJ to be successful in that environment?

Being able to bring solutions to the problems and not just bring problems without solutions was the number one key thing that enabled DJ to be successful in that role. He would always come ahead with solutions to their problems in terms of how to improve things and how to move things to the next level.

Being able to be more strategic and start behaving like a CEO is what leveled him up. It enabled him to be able to take on new projects because he's able to look at issues that the business may be facing today or might not be facing but could be facing in the future. His number one trick was coming up with solutions that can drive more impact on the business.

Behaving like a CEO

What does it mean to behave like a CEO?

It means to take ownership and give yourself permission to make decisions.

A lot of people think that they can only do leadership-type activities if they have the title. But actually, true leadership comes from those who lead from the front, regardless of what your title says. It's more about your actions and the impact that those actions have on an organization.

If you are the CEO of your own career, everything is within your control. You're the only one who can make the call on what's right for you. You can find mentors to help you improve. But you are the CEO of your own destiny.

And if you want to get to the next level, find someone who is at that next level, ask them how did they get there, and then follow in their footsteps. Take bits and pieces of knowledge that they've given to you so that you can move forward to the next level.

Oftentimes, promotions don't come from within the same organization. You can give yourself a promotion by applying for another job that has the role that you're looking for. And if your manager does not see your worth, there is someone else who will. Don't be discouraged.

Passion projects

Over the past decade, DJ has run an array of passion projects.

He has done everything from two-sided marketplaces, and job boards to publications and small apps alongside his day job. That was only possible because he has automated a lot of them. He can do all of those because he has taught himself some of the engineering and web development things on the side.

What he's been doing for the past couple of years was testing and experimenting with things. If his ideas work after testing, he would take that and implement them in other organizations. It's those projects where he's able to test experimental ideas, see an exponential increase, and then bring them into his organization. He just tries and replicates the same thing, tweaks a few things, and then he sees similar results.

DJ always has a testing mind. He will always keep hypothesizing. He always tries to think, What if there was a way to do this better? He always takes a step back and says, "What if..." and then looks at things from a different perspective.

The parallels of testing

What do testing ideas and managing people have in common?

When it comes to managing people, you always have to be testing different ways of communication, in terms of delivering feedback, refining your leadership style, and how to manage your teams and making sure that they feel psychologically safe.

What do you do to make your team feel psychologically safe in your workplace? You come up with an idea or a hypothesis.

If you tested your hypothesis and it doesn't work, that's okay. Try something else. Just continue having those ideas and keep testing them to improve your leadership skills.

David's advice to himself

What advice would DJ give his younger self?

He would tell himself to continue doing what he's doing but try to identify problems that will move the needle in every situation possible. He would also tell himself to do that outside of his day-to-day role in different departments because using it in your department alone doesn't mean that the problems you solve are only going to affect your department.

So he would tell himself to get more involved in the work of what other people do and try to understand where to discover new problems that they're facing, and try to come up with solutions for them.

You wouldn't believe the kind of strategic projects and opportunities that you could uncover from other teams. The bigger the organization, the more projects there are.

It will enable you to see outside your own worldview, and that is what will enable you to be a better leader, to be able to look outside your own peripherals and see the forest.

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