Illustration by  
January 18, 2022

“You should never be bored because there is always something to learn.” Jen Ruiz takes her love of blogging full time

Words by  

All of us aspire to accomplish our professional dreams, no matter how conservative or out of reach they may seem. However, the number of people who work to make their dreams a reality is significantly lesser. And the number of people who achieve this success is even fewer, with uncontrollable aspects such as luck and timing being crucial factors. Jen Ruiz, a millennial lawyer turned travel blogger, is one of those lucky few to have made such a transition and to have done it so succesfully. Read on to know how she did it.

Why did you make the transition from lawyer to travel blogger?

I started a blog in 2014 as a way to have a creative outlet. My first article was published when I was a volunteer contributor at Elite Daily. After some articles got traction, a travel editor reached out to me about paid work. Then the year before my 30th birthday, I took a ‘12 trips in 12 months’ challenge while I had a full-time job. I realized I enjoyed traveling a lot more than being in a courtroom. I was determined to make a meaningful income online, which I kicked off by publishing my first book. Once I saw I could develop online income streams, I quit my job to devote my full efforts to growing my online business. I matched my attorney salary with online income within the first year. 

You are a travel blogger, a social media influencer, an Amazon author, a keynote speaker, and a consultant. Was it a conscious decision to take on diverse roles?

As a digital entrepreneur, you end up wearing many different hats. You will never be bored because there is always something to learn. I ended up diversifying my income streams and finding diverse ways to share, market, and monetize my core expertise. It happened organically in my search for financial security.

For instance, I have a core skill set in travel — finding affordable flights, traveling solo, etc. I also have entrepreneurship skills. I looked for different ways to share the information I knew, from blog posts to ebooks to webinars. People learn in different ways, and you’re providing your audience with more options to absorb your content. You’re also adding new income streams along the way.

I’ve seen a lot more freelancers online due to ‘The Great Resignation’. However, even as the industry becomes flooded, professionals will stand out. For example, there is a big difference between writers and creators that know how to briefly and efficiently correspond with editors and pitch marketing proposals to brands versus those who give away freebies and fail to state their value proposition.

How do you ensure you find good, well-paying work consistently? Especially as you travel frequently and work remotely?

I have a mix of consistent monthly income, like social media management and blogger revenue, as it takes the pressure off finding sponsored campaigns or freelance articles every month. When it comes to freelance writing assignments, I like to peruse Twitter since editors are active here. I search for specific hashtags like #JournoRequest and #WritersWanted to find more work. I also follow a lot of editors and freelancers to see their updates in my feed. As a travel blogger, I also get paid for the photos that I contribute to an article.

Be it freelance writing or working with brands on campaigns, your pitching game has to be strong. I make it a point to follow up two weeks after sending the first pitch. If the response is not favorable, I approach another editor or brand, and so on. Giving up is not much of an option in this life. 

I also attend travel conferences regularly. In a world of pitching to mass inboxes, meeting with brand representatives at conferences helps establish a personal connection. Doing this is also a great way to collect business cards for future reference and find potential partnerships.

 As a digital entrepreneur, you have to keep hustling. I’m always looking for more publicity, collaboration opportunities, testimonials, and awards to help raise my rates. I stay on top of social media trends to create the next viral video or land a bigger brand deal. It’s a lot of work, and it helps to have a community of like-minded people to discuss problems that may come up and help each other succeed.

Building a personal brand is vital today, and you have mastered that. Could you share some tips on how to grow your social media?

Many creators will refuse to admit this, but social media today is as much about quantity as it is about quality. This secret is what helped me grow my TikTok account to 194k+ followers since April 2020. Of course, quality matters too. Also, the kind of content you put out will attract similar followers. For example, if you want to speak to young professionals, cringe content will not interest them. It will probably appeal to teenagers, who are not your target audience.

That said, the best way to know what will work is to produce often and always test your ideas. I try to post every day. You also need to give people a reason to follow you. Be clear on the value you offer. Instead of obsessively growing your followers, focus on engaging them. Also, always have a clear call to action; make sure to ask viewers to follow your account.

Go ahead and check out your competition; it won’t make you any less authentic. Identify 2-3 accounts that you want to emulate. Study what made their top content popular. Identify trending sounds and hashtags. Find a way to be entertaining, informative, or inspirational. Your content should be something that people will not only like but also share and reference later.

You have worked with major brands like Samsonite, Airbnb, and Celebrity Cruises. What is your secret?

I make it a point to be professional throughout my brand campaigns. In the beginning stages, I share media kits and case studies with brands to show them what I can do. I then identify their goals and send a full-fledged marketing proposal. And after the campaign is over, I send over a detailed case study.

I also gather testimonials from brands and screenshots of feedback from followers. Having happy, positive reviews to exhibit helps establish trust with my clients.

Your blog, Jen on a Jet Plane, encourages people to go on budget trips. Are young people your target audience?

 A lot of people think travel is cost-prohibitive. However, by finding an affordable flight, the world becomes much more open. It’s easy to find budget lodging and food options almost anywhere you go — the flight is the biggest challenge because it is expensive. Choosing the right flight is even more crucial for young people. They are the most overworked and underpaid!

Some of my favorite ways to save money on flights are to sign up for flight alerts, fly with budget airlines, and use miles. Budget airlines make travel a lot more accessible to many of us.

Speaking of challenges, what do you do to ensure that you switch off from work while traveling?

Even though it is far from easy, unplugging is a must. To enjoy my trip, I like to take care of any important deadlines or content before I go. If I have any deliverables due during my trip, I only have to hit the post button. 

I prioritize rest and build free time into my itineraries. I also recommend having an away message sharing what you’re doing, especially if you’re attending a conference in your field or are on a press trip. It sets reasonable expectations about how long it will take you to reply and simultaneously promotes your endeavors.

The pandemic had a severe impact on the travel industry. How did you manage to stay afloat?

I adapted. I pivoted from sharing travel content to talking about remote work. TikTok also helped me gain new followers and publicity. And I wrote two books about remote work that did well, given the timing of their release.

Further, I did a lot of virtual speaking events and said “yes” to almost every opportunity since I was doing them from my home office without any travel requirements. I got creative about digital press trips and campaigns. I did cooking classes with the Thailand Tourism Board and promoted Bentonville, Arkansas, in a virtual conference appearance.

While you are living the dream, a lot of work goes into sustaining it. Tell us how you unwind and prevent burnout.

 When I’m not traveling, I follow a routine as much as possible. I start my day with an audiobook to learn something new and get in the right mindset. Then I work out. I am an early riser and do all of this before 10 am.

I do priority tasks in the morning and post and engage on social media later in the day. I like to cook, especially since I’m always eating out while on the road. I also think it’s important to prioritize self-care, so if I need a day to watch Netflix and relax, I honor that. 

On average, I work about 7 hours a day. But if I’m on a press trip, I have to work a lot harder, sometimes 15-18 hours/day. I might work on weekends, depending on what projects and deliverables I have. I sometimes do more leisurely travel on weekends so that I can generate content to post.

What does it take to be a successful digital nomad in 2021 and beyond?

You have to be okay with failure, rejection, and slow growth at times. All of this is a part of the process and the self-employed life. You need the drive to stay consistent even when you fail to see results. 

Diversify. The more income streams you have, the more secure your finances will be. Diversify so that you don’t have to depend on a single client or source of income. Focus on passive income streams. In my case, they include ad revenues on my blog, book royalties from Amazon, and course sales. Once you have substantial passive income, you can stop trading your time for profits.

Learn how you can turn your freelance gig into a money making business. It’s FREE!

Free 15 min freelancing consultation call
Advice and practical steps to level up your business
Learn how to consistently find work
Get tips for finding your niche

Recommended Reading

How to make your business more cost effective in 2022

Review your subscriptions Evaluate your phone and internet providers Don’t expense for the sake of it Think about where you’re working from Sell off excess equipment The UK has been experiencing a cost of living...

A Field Guide to Bad Clients (and how to deal with them)

What we suggest 1. Get a contract that secures weekly hours2. State your terms at the bottom of every invoice and outline your late fees3. Don’t reply to emails outside of work hours. Schedule your reply to be...

How should journalists build their social media brand?

For better or worse, I can almost guarantee that every young journalist will have come across the phrase “JournoTwitter” at least half a dozen times as they work to break the glass ceiling in their...

Writers beware: Avoid the content mill

Like many other freelance writers, I stumbled into the industry somewhat by accident. Before COVID-19, I had been living a cushy life abroad, basking in the satisfaction of not having to update my LinkedIn. But...

Detaching self-worth from work

This second instalment of the self-worth and work topic will focus on the people who are actively working on detaching their self-worth from their work. I have struggled with this task ever since I dipped...

How to network as a freelancer in 2022

A common misconception about freelancing is that it’s only something you can do after you’ve established yourself within your industry. This is because freelancing is something many people do later on in their careers, having...

Defining your time; or how to avoid being on call 24/7

Defining your time; or how to avoid being on call 24/7

Don’t be afraid to set your own time. That’s probably why you became a freelancer, after all.

Is email killing your freelance productivity?

Is email killing your freelance productivity?

Emails are great. But they can also really really slow you down. Here are some ways to make sure your most useful tool doesn’t stop you from actually doing work

Do not let non-competes kill your business

Do not let non-competes kill your business

Non-competes can kill your business. Do not let them. Here’s how

Freelancers, this is how to take control of your money

Freelancers, this is how to take control of your money

The 30% rule is going to make your life a lot easier. Make sure you follow it if you’re a freelancer looking to manage their money more consistenly

Retainer clients are the dream. How do you find good ones?

Retainer clients are the dream. How do you find good ones?

Consistency? Haven’t heard of her. But if you want to a place where you can take risks with your freelance career, retainer clients are the way to stability.

The magic word every freelancer needs to know

The magic word every freelancer needs to know

It’s often the first word we learn, but it’s the last one we’re willing to say. How can saying “No” more often be the magic word every freelancer needs to know?

How do you create a portfolio straight out of university?

How do you create a portfolio straight out of university?

Coming out of uni with only limited work experience feels like it means you can only apply for entry level roles. But uni students can build fantastic work-sealing portfolios with some small tips and tricks

Freelance networking groups: How to join in and build your business without spamming

Freelance networking groups: How to join in and build your business without spamming

Do you want to talk about your business on an FB group but don’t want to be THAT person? There are ways to discuss work without seeming self-serving. Click up to find out.

How to onboard new clients as a freelancer

How to onboard new clients as a freelancer

If you’re signing new clients, that’s fantastic. But the first and second steps of the relationship are vital to keeping things positive. Having a consistent onboarding system can get your started in the right place.

How to tackle portfolio procrastination

How to tackle portfolio procrastination

Making good portfolios is crucial for your freelance business, but it can be tempting to procrastinate. Check out UnderPinned’s Virtual Office for portfolio templates to fill and send to clients!

The difference between Portfolios and Proposals

The difference between Portfolios and Proposals

So you’re hunting for freelance work? Well, what do you say when a potential client asks for a proposal rather than a portfolio? Have a read to see.

Freelancing with ADHD

Freelancing with ADHD

Freelancing is for everyone. But a job that requires skills you struggle with can make freelancing with ADHD difficult. Hear from an expert and a freelancer with ADHD about how she makes it work.

How to go freelance straight after uni

How to go freelance straight after uni

How do you go freelance straight after uni? You honestly ask yourself if you’re ready, and then you just lean into it 100%. And you read this article to find out more.

Signs of a weak freelance portfolio that clients spot at once

Signs of a weak freelance portfolio that clients spot at once

What signs in your portfolio are you hoping that clients see? And what are you hoping will be good filler? Make sure you’re only putting things in there that you can defend

Ten actionable tips for freelancers to relieve their WFH fatigue

Ten actionable tips for freelancers to relieve their WFH fatigue

WFH has been tough. But, a year into the change for many people, there are still learnings to be had. Zoom past fatigue with our tips

Ten things you should never say to a freelancer

Ten things you should never say to a freelancer

Vent your client frustrations through us! A must read for anyone that hires/knows/ever talks to a freelancer, here’s ten things never to say to a freelancer

Kill The Boss In Your Head: Freelancing and Creativity

Kill The Boss In Your Head: Freelancing and Creativity

Through the tension and anxiety at the heart of all paid freelance work, what are the conditions that best support the free-flowing of creativity?

One year ago I turned to freelancing to save my mental health: Here’s what happened

One year ago I turned to freelancing to save my mental health: Here’s what happened

Fiona Thomas writes on her switch to freelancing pushed by her mental health, and how someone in a similar scenario can benefit from the change

A guide to being a creative freelancer without social media

A guide to being a creative freelancer without social media

We could all do with a break from social media. But how do you continue to run your creative freelance business without your Instagram? Here’s a guide.

An extension of your arm: Must-have tools for freelance content creators

An extension of your arm: Must-have tools for freelance content creators

Want an aresenal of tools in your pocket that can make your freelance life expontentially easier? Look no further

The role of the creative brief and why it’s so vital to get right

The role of the creative brief and why it’s so vital to get right

Here’s how to be clear with clients about what you need from their brief, and what they should expect from you too in the beginnings of the conversation

Building it alone; Freelancing when you’re single

Building it alone; Freelancing when you’re single

Being freelance is tough enough. But doing it all alone can make it a lot more complicated. Here’s how to take some steps to make it easier on you.

A guide to juggling multiple freelance clients

A guide to juggling multiple freelance clients

You want freelance success? You probably will need more than one client. Finding them is one thing, but keeping them organised? Oh boy. Luckily we have a guide just for you.

Freelance journalists, here’s how to make ALCS work for you

Freelance journalists, here’s how to make ALCS work for you

If you’re a freelance journalist, you might have a chance at passive income from the ALCS that you didn’t know about.

How writers and journalists can make money with Substack

How writers and journalists can make money with Substack

Want to escape from the editorial loop? Substack is on everyone’s lips right now. But how can you use it as a writer?