How I Went from Being a 14-Year-Old Freelancer to a Tech Consulting CEO

In 3 Not-so-easy (but Totally Reproducible) Steps ... 

Imagine a baby-faced, 14-year-old teenager, obsessed with a virtual pet game (Neopets), taking up freelance design and development projects from people around the world. Nine years later, she runs a full-service digital agency to help people start and grow their online businesses as founder and CEO.

That’s what people see: the achievements I’ve made over the years, while I was quietly working my way through the plans I’ve laid out for myself behind the scenes.

There were so many challenges along the way, some unique to my journey, some which were lessons that every entrepreneur had to go through. Though every entrepreneur’s experience was a little different one from the other, the lessons that we learn out of it are more or less grounded on the same principles.

Step #1: I Realized the Importance of the “Doing”

It’s not enough just learning from someone else’s story—their failures, their successes, the steps they took to get to where they are. We humans learn through the doing, gaining the valuable experience unique to our situation and life. Instead of spending all your time reading business books or attending panel events, go out there and get started on something.

Maybe that’s an idea that you thought of recently. Spend less time thinking about how this idea will fail you. Worry less about the people who doubt your idea (or who doubt your capabilities to see it through). You cannot predict where you might fail, and you cannot foresee the lessons you’re going to learn from it. Sitting there and talking about your ideas and goals gets you nowhere and essentially helps you learn nothing about yourself and your capabilities. Self-doubt and self-defeating trains of thought are not uncommon to people in the C-suite or entrepreneurs, and they can impede you from taking the first couple of steps of doing.

Don’t get me wrong—it’s not going to be a piece of cake. That’s where you learn and grow.

My personal experience:

I wanted to build a small team of three highly skilled designers and developers when I was 17. The number of design and development projects started to increase beyond my bandwidth. I was still studying at a vocational school then and had an insurmountable number of tasks and assignments to complete. I had to look for people who are capable, responsible, and talented self-starters to help share the workload.

Although I knew what skills and talents I was looking for in the people I wanted to work with, I had zero experience interviewing people. I had no idea what I needed to ask, how I should have phrased certain words or sentences, or how I should’ve conducted the entire interviewing experience. Best of all, I was 17. No one took me seriously.

I could have sat there and read business books all day, or watched Youtube tutorials, or tune in to podcasts, or seek a mentor to help me solve my problems. But I chose to go ahead with the “doing.” I braved through storms of harsh words and criticisms of older adults who didn’t want to work with a teenager. I accepted the doubts people had in me, and pushed through.

Eventually, I found three people who were willing to work with me on projects I had remotely. This experience helped sharpen my knowledge about working with people within and outside of your organization, and finding the right fit for your team.  As a teenager, this experience was a rather brutal one for me—I found myself thinking self-doubting and self-defeating thoughts after interviewing some older creative professionals who didn’t imagine themselves working for a much younger person. In hindsight, I’m thankful I took this step. It has helped me boost my confidence tremendously.

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Step #2: I Embraced the CEO Mindset

Embracing a CEO mindset means starting to think about your business as more than a skill that you can offer, finding ways to grow and invest in your business for the long run, and invest more into the branding of your business.  

Freelancer’s mindset:

  • project-focused
  • Values the short-term returns more than the long-term  
  • Can treat what they do as a hobby, or as what defines them

CEO’s mindset:

  • Business-focused: Looking beyond one project
  • Values long-term returns over short-term returns
  • Thinks of their skillset as part of the business, and not what defines them as a whole

The way we carry ourselves and treat our business directly affects how others perceive it, and how you perceive yourself. Start thinking of your skill as part of the business, and identify weaker areas where your business can afford to invest in.

My personal experience:

For me, that was looking at my skill set and what I could offer to my clients, identify the skills I lacked, and find talented people who could help boost the offering and returns of each project. I started looking at the long-term survivability of the business instead of looking for freelance projects I could take up when I needed to.

I shifted my focus to building a pipeline and fulfilling the pipeline instead of waking up to look for projects every single day. My tasks suddenly expanded outside of design and development work. I was managing and growing my business’s pipeline, managing projects and people in the team, as well as the clients we had. Investing in my business has changed my game significantly. Other than setting up a proper LLC, a book-keeper, and setting up a business bank account, I also invested in paying for smaller tasks like social media management and client email management for $20/hour, so I could focus on tasks that would bring in more than $150/hour.

Step #3: I Chose to Invest in Myself

As a business owner and CEO, you have very little time on your hands to seek personal growth. With that said, you must not make the mistake of not taking enough time or effort in investing in yourself to be the best version of yourself. When you take the simple act of becoming a leader as CEO, you’re taking on more responsibilities as well. When your scope of responsibility grows, it will soon encompass other people - your team. For you to deliver these responsibilities, you’ll need to have the capacity and ability to do so. This is why investing in yourself is so important. Avoid overwhelming yourself with too much content, workshops, events, and opportunities for growth (such as panel events). Identify your strengths and weaknesses for a start, and prioritize where you’d like to invest in yourself. It’s easy for us to find hundreds of faults within ourselves, and it’s important to identify which ones you need to solve first for you and your business.

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My personal experience:

My transformation from freelancer to CEO meant I quickly turned from project management to people management. Although I have had some helpful experience in the past assuming leadership roles in school and programs which I volunteer for and spearhead for various charity work, it was an entirely different experience managing people remotely as a remote CEO.

When remote team members are in a disagreement, there’s not an easy outlet to let off some steam or to vent. There’s no cafeteria corner where everyone could huddle and vent over coffee. The timezone difference makes it difficult to have proper, real-time conversations to help facilitate and solve these disagreements. In fact, if as a remote CEO, you’re able to witness this disagreement, you’ve pretty much lucked out: most disagreements happen between private chats or emails which you’re not copied on or aware of. T

his became my key area of focus for self-improvement: managing people better, online and offline. Instead of going for just about every leadership workshop or webinar available to me,  I decided to specifically seek out business owners who were working remotely or managing remote teams, and share our strategies and problems which we faced.

As a leader, you always have influence and control. If you’re a leader who places importance on improving herself, your team will inevitably follow suit. When you grow your team into people who always look to improve themselves constantly and consistently, you’ll find much reward and motivation to pursue bigger goals for your business.

Investing in yourself as CEO goes a long way: for yourself, and your team. Becoming a CEO is only the start of a new phase in your life. It is an entirely new experience with a lot more responsibility to shoulder. It takes a lot of strength to remain the beacon of hope for the rest of your team during bleak times, humility to take the backseat when you help your team grow their capabilities and skills, discipline to remain focused when things are going very well for the business, and awareness to be able to stay truly aligned with the desired outcomes they want for the team and business.

As a remote CEO, I’m committed to creating an environment where people feel comfortable saying what they need or desire, online and offline. I’ve come pretty far since I freelanced as a teenager, but I will have much room to grow to becoming the best leader for my team and my business.


About the Author

Cherie Tan is founder and CEO of Mogul Tech International, which helps entrepreneurs launch and run online businesses. Aside from the day-to-day communication and work with her remote team at Mogul Tech International, she is working on a side project in Education: Weevur: a platform to facilitate skill and knowledge exchange to help make quality education more accessible.