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[EHN-002] This week: finding clients, travel budgets, healthcare and more...

Weekly Waypoint

How and where to find clients and get more stable freelance work

Many people advocate doing a bunch of things that just don’t work to get clients. Supposedly “helpful” articles on finding freelance work tell you to do a bunch of things like network, write guest posts, lurk on Twitter. I once even saw someone say to “be social.” 


These things are just shiny distractions.

If you spend your time doing all of these “busy things” to feel like you’re working, but they aren’t worthwhile, then you’re going to get frustrated and give up quickly.

Identify where your clients are and what freelance work they need, then serve them accordingly.

There’s plenty of freelance work out there, you just have to find it. And it doesn’t come from doing a bunch of random things, but instead from having a clear focus. When you make finding freelance work (and only that) your guiding light, what you should be doing becomes clear.

There are two main ways to go after clients. Using freelance platforms or finding clients yourself and cold pitching them.

The majority of people focus on where to find freelance jobs, versus going out and creating a job for themselves, so we’ll cover that first. Many start out on platforms and then work on figuring out how to get freelance clients on their own later.

There are numerous online sites out there that try to connect freelancers and clients. Upwork, Freelancer.com, and Fiverr are some of the most well known names, although there are many others as well.

These platforms charge fees for submitting proposals, and competition can be fierce. So although platforms can provide a starting point for beginners, they lack the proactive approach of seeking clients independently.

Finding clients on your own is a game changer.

It involves a proactive mindset, actively showcasing how you can solve their problems, and explaining why they should choose you.

Let’s take this example: One of my clients needs a rockstar executive assistant. This person will mostly work with me, although in a larger sense the organization as well. We need someone who is up for whatever, a right-hand man or woman who will report to me and manage anything that I or the CEO throws his/her way.

Seriously, I need this person to become my right-hand. I’d put that in the job description title if it would make sense.

But here’s the thing … while I know I need this person, even when I find the right person, I essentially have to do a brain dump, getting everything out of my head and into theirs.

This is the scattered thought process of so many small business owners. We have a need, but we don’t prioritize filling that need for weeks or months because of the many urgent day-to-day things on our plate.

When you can show up to the right person, magically drop into their inbox, and solve their problem, you will have made yourself invaluable.

Thinking about the example above, what if an awesome virtual assistant showed up in my inbox with a great pitch, showing me examples of how s/he has managed all kinds of work before? What if s/he knew a little bit about my company and probable needs, and offered to help me out? I’d jump at the opportunity to learn more.

With this approach of proactively getting in front of the client, it reduces their workload. Even though some things can’t be eliminated completely, I don’t have to do the job posting, review candidates, interview them, etc. Instead, I can have an interview with this candidate who has already shown themselves to be proactive and if they’re a good fit, hop right into the training and onboarding.

Can you see the difference here? Between hoping and waiting for a client to notice you versus jumping up and waving, “Hey! Over here! You need me and I’m here to help!”

So where do you find these high quality clients?

On the internet of course! 

You’ll do the online equivalent of networking and meet people in FB groups, forums, and on social media.

You need to be in these groups meeting people and listening to people. Your goal is NOT to be spammy or sell people on stuff, but to ADD VALUE!

Building credibility within these groups positions you as an expert. People will recognize your expertise, and when the time is right, they might approach you for freelance work. Additionally, it clarifies which individuals are receptive to a direct pitch.

Facebook groups are not the only places to tune into what types of freelance work businesses need. Forums like Reddit and Quora can also be useful as well as good old Instagram.

This is how you get your own freelance clients.

You break the reactive model — sitting back, sending off a proposal among 50 other people and hoping you hear something. You build a powerful model  — “I am a business owner providing services to other business owners who need my solutions in order to solve their problems.”

Life happens: healthcare considerations as a freelancer!

Healthcare is a very important consideration when considering becoming a freelancer. Because it's so expensive, I’ve seen it hold many people back from leaving their employer and living their freelance dream. I’m not an expert on all countries but if you're living in the USA, health insurance is non-negotiable.

While it can be tempting to go without, especially if you've been mostly healthy always, just one serious incident without insurance can bankrupt you.

So as much as it sucks, you'll need to grab some. 

While this is handled by the employer if you're in a traditional 9-5, health insurance for freelancers can be purchased independently. 


It can be quite expensive so you'll have to make the decision on which plan to go with based on your age, life circumstances, medical history, etc. It's also quite different if you're just paying for one person (yourself) or looking at covering a family.

While I was living in the US I paid for a cheap plan that I joked was an “Only use this if genuinely dying plan,” because while the monthly charge was cheap— if I’d actually had a medical problem, it would have been expensive as hell.

Life happens! I ended up in a clinic in Medellín Colombia with an inflamed tendon in my elbow. Total out of pocket cost was a whopping $53 (including the visit, two IV drips, and prescription meds).

I made this decision based on my personal medical history, age, and the hope and faith that I would continue to stay in good health. If you have pre-existing conditions or medical concerns, or dependents, healthcare will be a huge part of your decision to get into freelancing and you’ll need to be sure you can take on projects and set rates that will allow you to factor in this expense.

Although it's possible to get a cheap plan for $100-200/month I encourage most of my freelance students (those still living in the USA) to set aside around $500/month for health insurance in order to be on the safe side.

My number one tip for healthcare however is to (if you can,) get on a plane and get out of the US. This is a huge benefit in choosing to work remotely as a freelancer. The world is your oyster and you can get out there and explore it. 

There are numerous digital nomad insurance plans that cover you at very affordable prices. Don’t let the name digital nomad insurance fool you. You don’t have to be constantly on the go. Most plans let you set your “area” so you can specify South America, (versus a specific country like Colombia) and you’re covered if you’re based in one place and then traveling around.

You can also look at picking up local health insurance if you’re staying for a while in a place that makes sense. Many times, you can also just pay out of pocket depending on the country. (My medical expenses referenced above in Colombia, for example, were so small that I didn’t even bother submitting the claim paperwork to my insurance company.)

Leaving the county full time doesn't have to be something you consider right away, but if you like to travel, it could be a long term consideration in the direction you take your life and career.

Spoiler alert: freelancing is really NOT that hard

No matter what type of work you do, I’ve identified 10 freelancing skills that will set you up for success. Today we are talking about the skill: Willingness to work hard.

Many people are shocked when I tell them that the #1 thing I wish people knew about freelancing is... "It's really not that hard." 

“But wait,” they say, “what do you mean?” This seems to contrast directly with the name of this freelancing skill...?

What I mean is that there are simple steps you can follow to create a successful career in freelancing — a 6-figure career if you're so inclined. The steps are simple, it's not hard, but you do have to be willing to DO the work.

Things like:

  • Going above and beyond to do solid research on a potential client's business. 

  • Reaching out and pitching clients even if it's scary. 

  • Putting in the hours once you've landed a project. 

  • Putting your name and high quality behind your work. 

It's work, but it's completely doable. If you've got a solid work ethic and believe in doing work of meaning and value, you've got one of the critical freelancing skills necessary for success.

As we continue our time here together, I will be sharing more of my top 10, so don’t miss a single edition of the Escape Hatch! 🤗

My favorite done-for-you way to find cheap flights!

You work a full-time job, your calendar is full, and you’re just living for the weekend… ahh, but you forgot you’ve got your nephew’s 1-year-old birthday party to go to… so there goes Saturday.

Jetting off to the other side of the world sounds incredible, but how in the world are you going to find the time to look up destinations, let alone juggle dates?! Oh, do I have the service for you!

They’re called Next Vacay (and while they were one of my first freelance clients, and I still work with them, this is not an affiliate link and I’m not getting paid for talking about them). 

They are the ultimate in done-for-you flight finding! 

You might be thinking, “If I’m looking for ways to find cheap flights, how in the world does she think I can afford a flight finding service?!” But the reality is you can’t afford NOT to use them for what they save you in time.

The membership price is a stunningly low $25 per year! And depending on the size of the city you live in you’ll receive anywhere from 5-20 deals per month to amazing destinations all over the world.

How it works

Let’s say you live in Newark, NJ:

  • You go to www.nextvacay.com and sign up entering Newark as your departure airport.

  • You’ll start to receive several deals out of Newark each week (surrounding airports like all of the NYC airports are included at no extra cost).

  • The deal email contains the dates the deal is good for, typically a range like May – November and the link to the flight. You click the link, figure out the dates that work for you, and book directly with the airline so you can use points/miles if you’ve got them.

A few more quick points about Next Vacay

  • There is a free trial of 30-days so you can try them out without spending a dime.

  • They further offer a full 6-month money-back guarantee once your actual membership starts. So if you don’t see any deals you’re able to take advantage of (think your stingy boss frowns every time you even mention vacation) you can get your money back no questions asked. (That’s technically 7 months total to “trial” the product!)

  • They send deals that are up to 10 months out, so there’s no need to drop everything, pack and leave the next day. In fact, they avoid sending last-minute deals unless it’s something like an exceptional holiday find.

  • All deals are vetted by real humans who love to travel so they make sure you’re not getting long layovers, or heaven forbid, switching airports like JFK to LaGuardia during a stop.

  • You’re booking directly with the airline so saving on any 3rd party fees and avoiding any booking snafus.

  • One of their coolest features is that they are not just US-based. While they serve a ton of airports in the US, they also have membership airports in Canada, Australia, and Europe with more being added every year.

Instagram Spotlight

I’ve been traveling the world for over 15 years (in fact my first flight was abroad – nothing like jumping in with both feet!) and along the way I’ve found a number of tried and true ways to find cheap flights to anywhere you want to go.

Check out this reel and use any or all of these tips to find cheap flights and you’ll be packing your suitcase and heading to the airport in no time!

Leave me a comment while you’re there and let me know you are an Escape Hatch News subscriber.

Click the image above and follow me on Instagram where you’ll find even more Live, Work and Travel tips, tools and resources.

Roadmap to $100K