From the moment I officially entered the full-time workforce (and even before), I wanted freedom.


I always wanted to make my own choices about the clothing I wore to work, when I focused on my work, and eventually– the itch to be in charge of the content of my work became something I had to scratch.

I worked 6-months of W-2 salaried employment and happily waved goodbye to that world.

Just Under a Decade of Freedom (and Flexibility)

In July of 2011, I created my first company and shifted to independent contractor status (with my previous employer).

While there are still some who prefer the (illusory) safety of employment, I couldn’t stand the restrictions.

The thought of someone else making a profit from my labor detested me.

The only thing that felt worse was the idea of them losing money on me.

work wherever whenever freedom flexible jobs laptop woods forest

The Future of Work

With the gig economy in full-swing and reasonable wages available on-demand, the underlying value systems of the masses are being revealed.

We want FREEDOM.  We want to work where, when, and on whatever we want.

We are shedding the skins of security and stability, in favor of flexible lifestyles.

What are the [top] perks of the digital worker’s lifestyle?

  • Working whenever 
  • Working wherever
  • Working on whatever you want

This is the real meaning of “www…” (just kidding)

flexible job work freedom lovers

But let’s face it.

The shackles of corporate life are growing too heavy for millennials (among other generations, both younger and older) to carry anymore.

The systemic market shifts of the past 5-10 years are brought about by an undercurrent… the pursuit of Freedom.

We buck against the “cons” of corporate life…

  • Do what you’re told
  • Make a profit for “the man”
  • Be in the office early (before 9:00 am)
  • Stay in the office late (after 5:00 pm)
  • Take a minimal vacation (a story about that)

Now, what can you do to create more Workplace Freedom in your life?

You don’t have to make a 180-degree shift overnight.

But you can start right now.  You can begin today.

In fact, you’re already getting started just by reading this article.

Qualifying the “Most Flexible Jobs” (of 2019)

For this list, we score each of the “jobs” by how much freedom it provides the worker in the short-term AND in the long-term.

  • Short-Term Freedom focuses on immediate benefits but does not consider a long-term time horizon.
  • Long-Term Freedom asks, “How much momentum can this ‘job’ attain for me?”

A high score for long-term freedom means that you’ve built an asset.

You’re building something that will snowball.

long term benefits of gig economy and flexible freedom jobs

This can either be the growth of a personal skill set that increases your intrinsic value (hourly wage, for example), or it could be the growth of an asset outside of yourself (equity in a company, for example).

An important consideration with gig economy jobs, for example, is how disposable workers are.

So, we’ve ranked these jobs based on their total score, including both short-term and long-term benefits.

Short-Term benefits are scored based on the ability to work “wherever, whenever, on whatever”.

Flexible Online Jobs for Freedom Lovers

Job TitleShort-Term ScoreLong-Term ScoreMonthly Pay Potential
Freelance Writer9580$25,000
Social Media Manager7045$5,000
Website Developer6575$10,000
Virtual Assistant9060$5,000
Niche Website Creator5085$3,000

1. Blogging (and online media creation)

Short Term SCORE: 14 points (this one takes a while)

Long Term SCORE: 100 points

Potential Yearly Income: $1000-$100k+

Short term goals: Work on gaining traffic. In your first year, aim for at least 100/visitors per day

Long term goals: Build an income-generating brand that will be live for decades

blogger typing on laptop on a couch

This is our favorite pick. You could say that this is the pillar of your online empire – if you seek to create one. And, short term, it’s a job with flexible hours.

Having a strong online presence isn’t a luxury anymore. It’s a necessity. As we shift to the new paradigm of remote work and natural networks, your blog will act as your new business card.

But it can be more than that. It can become a powerful brand that’s effectively your reputation. An expectation you impose on others.

And that can open many doors for you.

Depending on your skills and your interests, you can start creating your blog TODAY and begin connecting with like-minded individuals. From the comfort of your home. The mountains or the beach!

“OK, but how am I suppose to make…you know, money?”

There are many ways to monetize an authority blog:

  • Ads
  • Affiliate marketing
  • Consulting
  • Infoproducts
  • Merchandize

But you don’t have to limit yourself. Remember the 3rd W? “Working on whatever you want”.

What interests you the most?


What skills do you have?


How can you help people?

If you can genuinely help people solve their problems, using your expertise, you’ll never have to worry about money again.

The best part is that a blog is like a real estate. It never goes away (unless you stop tending to it) and you can grow it, sell it, remodel it, etc.

It’s definitely a long-term option. A few years of work can lend you a lifetime of freedom and economic stability. But there are also some options to do this fast and have a great ROI in a few months. See #5.

Remember, you’re building something (a long-term asset)

building with tools

2. Freelance Writing

Short Term SCORE: 95 points

Long Term SCORE: 85 points

Potential Yearly Income: $1000-$300k

Short term goals: In your first year of business, aim to have 2-3 regular clients

Long term goals: Build your network and start delegating work


Are you excited about starting a blog? Well, you should be.

But here’s the thing. In order to amass the following and the necessary organic traffic to be profitable, months might pass by.

Yes, no one said is gonna be easy. Anything worth doing is hard.

Fortunately, there’s a way to start making money this week… if you have a knack for scribbling words.

Freelance writing is perhaps the fastest way to make your first $1000 online. 

author writing with pen and paper freelance writing

Here’s how freelance writing works, in 2 easy steps.

Step 1: Find a potential client you want to work with

(Step 1+: Give your business card (your blog) where he/she can take a look at your work)

Step 2: Send an email, connect, talk on the phone.

Keep it simple. Explain what you can do for this person’s business.

Now, do the above x100.

The 3 main paths to make it as a freelance writer:

  1. Copywriting: Writing words that sell – The most complex skill but the most profitable path
  2. Content Strategy: Writing content for other people – The most creative path but harder to make money
  3. Independent Journalism: Writing for newsmedia outlets – Very fulfilling, very hard

You should take into consideration your skills and disposition before you choose. If you hate selling, you shouldn’t be a copywriter, etc.

In the beginning, you might find yourself charging a lot less than your usual hourly rate. Don’t get discouraged. As you move forward become proficient in your craft, your rates will shoot up.

3. Photography and Videography

Short Term SCORE: 80 points

Long Term SCORE: 75 points

Potential Yearly Income: Depends on your niche

Short term goals: Build a social media presence

Long term goals: Work on your own creative projects


girl photographer with camera outdoors freelance photography

The internet is becoming more and more “visual”, with users seeking more and more content. Instagram and Youtube alone amass millions of views per day.

This is where you come in. For most people, photography is merely a hobby. And that might be the case for you as well.

But what if I told you there’s a way to monetize it and perhaps make enough money to quit your 9-5 job?

Long gone are the days where you had to go around town in order to showcase your portfolio. Now, you can upload your work online and the right people will find you. After all, we’re looking for jobs with a flexible schedule.

That said, there’s a lot of competition out there.


So, how are you going to stand out? By choosing the right – for you – photography/videography niche:


  • Portraits
  • Landscapes
  • Events
  • Street photography
  • Photojournalism


You’re not over! Niche down. One quick way to do that is by writing this simple sentence. For example:

“I’m an [event videographer], focusing on [women’s fitness-related concepts] for [local gym brands]

You don’t want to leave anything in their imagination about what you do.

guy photographer with camera outdoors

Use social media or your blog to post your stuff and start networking.


Pro tip: People need to feel a connection with you before choosing to work with you. Don’t be afraid to write a few things about your process.

4. Virtual Assistant

Short Term SCORE: 90 points

Long Term SCORE: 60 points

Potential Hourly Income: $15 – $100

Short term goals: Do this a few hours per week until you’ve gained enough experience

Long term goals: Become indispensable


virtual assistant notes planner

People, more often than not, underestimate what a VA can accomplish. Before you choose to become a virtual assistant, make your own hours, and work for entrepreneurs this is what you’re going to be doing:

  • Strategize and create comprehensive business plans
  • Manage websites and social media
  • Respond to emails and make the sale
  • Create actionable plans to streamline projects
  • Coordinate team to kickstart product launches

Even though this is the best choice if you want a flexible part-time job, this role can evolve to something more permanent.

Keep in mind many companies offering these services.

But entrepreneurs prefer the personal touch of a committed VA. It’s up to you to become indispensable and contribute to the business in a meaningful way.

Don’t be afraid to ask for more. Show your skills and become part of the company!

5. Niche Websites

Short Term SCORE: 50 points

Long Term SCORE: 90 points

Potential Monthly Income: $100-$3000

Short term goals: Create 2 profitable niche sites in 6 months

Long term goals: Create multiple appreciating assets you can sell
Niche websites are the epitome of a flexible job. You do the work for 3-6 months and then you’re making money in your sleep.

Niche Site vs Authority Blog

Niche SiteAuthority Blog
Posts about one niche subjectPosts about things that interest you
SEO: Focuses on keywords with buyer intentionSEO: Focuses on a long term strategy
Pros: Easy to createPros: Huge potential ROI
Cons: Has an income ceilingCons: Will take time
Smaller website requires less workLarge websites, you can get super creative

(share on social media using the image below)

Niche Site Vs Authority Blog pros and cons

Internet marketers used to say that you can create a niche website in one weekend. There’s some truth to that.

In order to find a *profitable* niche, you need to test a lot of different things. That means you’re going to work on multiple sites at once.

But each one will have “bare bones” content: 5-15 posts max, usually reviews of a product. If you start gaining traffic after a few months, you can add more.

Monetization: Affiliate products, ebooks, ads in some rare cases.

Niche sites are the perfect way to test your ideas before you try to create a huge, authority blog!


6. Podcasts

Short Term SCORE: 10 points

Long Term SCORE: 80 points

Potential Income Per Episode: $0 – $3000

Short term goals: Acquire a decent setup, upload consistently

Long term goals: Get a loyal fanbase


Did you know that most podcasters won’t make a dime?

Since most podcasts don’t get enough traction to generate interest from advertisers, they end up shutting down.


But if you truly want FREEDOM and a flexible job, you will make it work. How?


Take advantage of every platform out there. Own every aspect of your show.  

Podcasting should be about a few people talking about interesting subjects. It doesn’t have to be complicated and you certainly don’t have to pander to advertisers.

Some of the most popular podcasts were a product of distaste for the dull, company-controlled radio.

Instead of relying on third parties giving you money, create your own products, your own offers and make them available to your fanbase.

Post your episodes on every platform available and blast your social media with links.

Once you have a few people tuning in every week, you’re set.

100 loyal listeners > 1000 lukewarm fans

7. Social Media Manager

Short Term SCORE: 70

Long Term SCORE: 45

Potential Monthly Income: $500 – $5000

Short term goals: Experiment and grow your own social media page to 1000 followers

Long term goals: Work with multiple big brands.


One of the biggest problems brands are facing at the moment is adapting to the ever-changing social media platforms.

Most companies arrived late to the party and now they have no idea what they’re supposed to do in order to gain traction.

This is where YOU come in.

what does a social media manager do?

I know what you’re thinking: “Me? I have a Twitter account with 300 followers. I certainly don’t qualify to be a social media manager!”

Like everything else, this is a skill and you have to practice daily to become better. Good news is that if you can do it one time, you can do it again and again.

So, here’s the strategy I propose:

  • Create a personal social media page about a subject that interests you
  • Slowly define your audience
  • Learn from your mistakes and adjust
  • Grow your account to a 1000 engaged followers in 3-6 months
  • **Do it one more time**
  • Showcase your work, from beginning to end, to a few different businesses
  • Profit!

Don’t think that you have to be the social media manager of some big, multinational brand. There are many brick and mortar, local businesses that are looking to enter the social media game but have no clue how the internet works.

Start with them!

8. Website Developer

Short Term SCORE: 65

Long Term SCORE: 75

Potential Monthly Income: $10k

Short term goals: “Sell” a functional, user-friendly website

Long term goals: Choose the projects you want to work on


You could argue that this is one of the most “popular” online jobs nowadays. And you’d be correct.

The market is saturated with freelancers who claim they’re able to finish a project in one weekend, only to deliver a “Twenty Sixteen” themed, 1-page WordPress site.

On top of that, there are plenty of relatively cheap services out there that can set up websites with the click of a button.

At this point, you may be thinking that it’s too late to follow this path.

What I didn’t tell you is how many entrepreneurs, startups, and big companies are looking for skilled, versatile website developers that can create UNIQUE sites, with a clear on-brand message.

If you believe you have these traits, then you have nothing to worry about.

And if you can take care of both the front-end and the back-end stuff, you’ll become invaluable.

One last word of advice: It’s very tempting to pump out and sell 100s of Shopify and WordPress pages. But it’ll get boring quick. Too many developers get burned out after their first year. Choose interesting projects, with people you want to work with.


9. Create your own product

Short Term SCORE: 90 points

Long Term SCORE: 90 points

Potential Yearly Income: Millions

Short term goals: Test the market

Long term goals: “Trigger an event”, ie launch a product


If you’ve read this far, you might have noticed the underlying theme of every flexible job that has the potential to break the shackles of 9-5.


Creating a product is the most difficult, but the most rewarding option on this list.

You control everything, from production to delivery.

But before you start buying samples and testing Facebook ads, you need to do your research.

One of the best ways to do that is to “stalk” competitors, people who are already selling what you want to sell.

  • Break down their process
  • Observe how they set up their funnels
  • What kind of ads they run
  • Who are they’re selling to


Keep in mind that it doesn’t have to be a physical product. It can be an info-product, a webinar, a course or even a small ebook.

The point is to create something of value. Something that YOU own.

But what if you DO want to sell a physical product?

Well, you’d need about $50.000 for design, initial samples, inventory, storage space, fulfilment, etc.

And if your product flops? You’ll have A LOT of one thing you can’t get rid off. That’s not good.

Fortunately, there’s a bulletproof way to test if your idea will work, without blowing away your savings account. It’s called dropshipping.

No, it’s not a scam. It’s not about peddling cheap crap or outright illegal products. There’s a legitimate way to do this.

For those of you who are not familiar with the concept, here’s how it works:


  1. You choose a product(s)
  2. You create a store
  3. You send traffic to your store — with ads or social media promotion
  4. People click “Buy Now”
  5. The information they’ve provided (address, phone, etc) are sent to the manufacturer
  6. The manufacturer takes a small cut and delivers the product


You’ll be surprised by how many influencers and well-known brands are using this method.

You need about $500-$1000 to start (you have to run ads eventually) and you can scale from there.

Good news is once you have enough money, you can design your own stuff and you’ll KNOW they’ll do well.

Dropshipping simply mitigates a lot of the initial risk and simplifies the process. Less moving parts, more room for experimentation.

If you don’t churn and burn your customers, you can create a solid brand!

At the end of the day, selling a product separates your income from your time. It really is a mindset shift.


“I need to work 100 hours to earn $2000”




“I need to sell 10 items to earn $2000”


What steps are you taking TODAY to escape the rat race and become financially independent?

If you want to earn your FREEDOM, start working from home and make your own schedule you need to do something TODAY.

Pick one thing from the list and start putting in the work. The most difficult part is to start.


Once you do, you’ll never be able to work a regular job again in your life.