How To Start Your Remote Work Journey

Don’t know how to make the jump from corporate to remote work?

You’re not alone.

Believe it or not, many remote workers, including myself, have been in this same situation. When I first considered being a digital nomad, there wasn't a lot of advice catered specifically for Filipinos.

That’s why in this post, I’ll do my best to share actionable tips on how I made the jump…and stuck the landing.

Let’s begin with the most difficult part:

1. Getting started

For most Filipinos, the hardest part about working remotely is getting started.

We’re held back by a lot of fears and uncertainties. What if it doesn’t work out? Do I have transferable skills? What will happen if I can’t support my family and put food on the table?

These are valid fears, but don’t let overthinking prevent you from taking action. You don’t even have to make a giant leap! You can start with small, measured steps and work your way up.

For example, when Shepherd was just starting out, I didn’t quit my “day job” as an operations manager at Need/Want. I continued working on my role until Shepherd reached a certain level of growth. And when we saw that growth, that was when I went all in.

You can do the same.

Start by taking side hustles or part-time remote work. See if you have the right skills and temperament to do remote work long-term. This is also a great opportunity to take on challenges without putting your income at risk.

Once you get the hang of it, go all in. Opportunity will eventually let you know where to focus your energies.

How to assess risk

“But Joemer, how do I know if I’m ready to take the risk?”

In an old blog post, our good friend Sam Parr from The Hustle shared how to measure risk and make good decisions. Here’s what he shared:

• Step 1: Write out the risk you're deciding on.

• Step 2: Make a list of possible worst-case scenarios.

• Step 3: Address each possible scenario. Can you handle or live with these scenarios? If not, how can you prevent them from happening in the first place?
  

In just three steps, you can now make a plan that hopefully minimizes your risk and increases your chances of success.

Taking measured risks may not sound “cool” or “adventurous”, but it can set you up for long-term success. Go for it — even when you have to do it slowly or cautiously.

Related: The challenges of remote work and how I got over them

2. Define your niche

I’m a huge believer in finding your niche. The world of remote work is vast. If you try to be a jack of all trades — working in every market and jumping from one skill to another — you’ll be a master of none.

For me, it’s better to start with one niche. It’s a great way for you to learn the ropes and gain focus.

How to pick a niche

I admit, picking a niche can be tricky. Here are the things that you can consider when choosing one:

• What topics or industries are you naturally interested in?

• What skills do you currently have or are willing to learn?

• What industries are willing to pay for these skills?

• What remote jobs are currently in-demand?

To get a clearer picture of the job market, check out Shepherd’s Career website and see if something fits your skills and interests.

3. Assess your circle

Setting out to work remotely is a big change. Many of your friends and family will question your decision. Make sure to surround yourself with people who believe in your dream and are willing to support you.

I call this tailoring my life’s algorithm.

I did this by physically and digitally associating myself with people who have proven that my digital nomad dreams were possible. I connected with folks who already had digital businesses or those who’ve already hit 7-figure incomes.

Not only did this inspire me — it also gave me the opportunity to learn from these people, too.

If your current circle is no longer aligned with what you want from life, look for people who share your goals, dreams, and values instead. Surround yourself with people who add value to your life — and make sure that you add value to their lives as well.

Learn more: Books That Changed My Life For the Better

4. Fall in love with the things you do

I don’t want to sound cheesy, but my last tip is all about falling in love.

Like many things in life, remote work is not always easy. There are times when you’ll feel lucky to be able to pursue it and there are days when you’d ask yourself: “ano ba tong pinasok ko?” (What did I get myself into?)

Remote work will test your patience and fortitude, so dig deep into your purpose. Don’t just fall in love with the results, but fall in love with the process and your vision. When you stick to these things, you’ll find the motivation to conquer just about any hurdle that life throws your way.

Remember:

“The man who loves walking walks further than the man who loves the destination”

Next, fall in love with building a business. Give back to your team. Take time to get together and end the week on a good note. Make your business such a good place to work that your team will have no choice but to fall in love with it too.

Lastly, fall in love with yourself. Be your biggest fan. Venturing out into something unfamiliar like remote work is a huge risk — and here you are, doing it anyway. That’s something that should be celebrated!

Enjoy the remote work journey

Taking a chance on your dreams is daunting. The good news is that you don’t have to do this alone.

I hope that by sharing my experiences, you’ll be able to prepare — and enjoy — this wonderful journey. And if you have any questions, don’t hesitate to connect with me on LinkedIn and Twitter.

Good luck and see you on the other side!