21 ways to quit your 9-5, work remotely, or work for yourself

If you’re looking to break free and pursue a less traditional career path, have an entrepreneurial mind, or have ever thought about starting your own company, there are a few simple things you can do to find yourself chasing something of your own rather than a traditional 9-5 if you so choose to. 

Shortly after deciding to drop out of community college back when I was 21, I found myself chasing a new alternative to the 9-5 grind working for a tech startup in New York City.

A year later I found myself working remotely while traveling and now find pleasure in working anywhere, but an office. If you're looking to shake up your work routine, here are the 21 things you need to implement to escape your 9-5, land a remote gig, and even start a successful side hustle of your own.

1. Clarify what makes you happy and unhappy at work

The first part of escaping your current state of operations is to make a list of what makes you happy and unhappy in your work environment.

Start by asking yourself the following: why do you want to leave your job, what don't you like about your current position, what are things you enjoy about your current position, what makes you unhappy at work, what makes you happy at work, are there parts of your job that you can't wait to abandon, are there parts of your job that you couldn't imagine your life without, what stresses you out in the office, what do you enjoy about your office, what external stresses do you feel in your personal life, how does work related stress transition into your personal life, and in a perfect world, how would you manage these stresses.

This workout will help you clear your mind of the negative clutter to help pave the path to your new life.


2. Draft a clear outline of your dream life

The next step to breaking out of your current gig is to sit down and draft a clear image of what your dream life looks like.

Ask yourself the following: what is your dream job, what is your ideal schedule, is your dream job one where you can work on your own schedule, is your dream job one where you're your own boss, how much do you want to work a day, week, and month, how important is work life balance, how important is work life flexibility, is your dream job one where you can work anywhere in the world, is your dream job one where you'll be paid to travel, eat, model, or write, and what does your ideal life not have time or space for.


3. Create an actionable plan 

Although plenty of people fantasize about the idea of ditching their 9-5 to pursue an alternative life, many people fail to take the first reasonable step towards that goal. Take the time to create and map out a plan to quit your job, then execute. Don’t forget to be realistic.

Some of the important things to include are: do you need time to advance your skill set to land your dream job, how long will this take, do you have the resources to invest in learning said skills? When will you start, what do you need to start your side business, when, what is your timeline for quitting, what milestones do you need to achieve before quitting, do you need to give your job a significant notice, how quickly do you want to quit, what kind of lifestyle do you want to live, are there things you can cut from your life to achieve this sooner, what are some things you'll need to sacrifice to get there, what are the risks of leaving your job, and how will this affect your career and goals.

Create a timeline with deadlines of small goals you can achieve along the way. Will you create a 3 month, 6 month, 9 month, or 12 month plan? Get specific and make moves.


4. Audit your finances

Speaking of plans, it's important to discuss and plan how this may affect your finances.

Ask yourself: what are your monthly expenses, how will this change if you leave your job, how much money do you need a month to sustain your lifestyle, how much money do you want to make a month, are here things you want to omit from your budget to achieve this goal, and are you prepared for a rainy day.

5. Declutter your life of anything that's holding you down

Decluttering is a great practice when you’re looking to make a major life change. It helps clear both your mind and your living space.

Ask yourself the following: are there people you keep in your life because you feel you have to, not because you want to, are there old habits you've been meaning to rid your life of, and have you accumulated a surplus of things that no longer bring value to your life.

One of my favorite bloggers is Joshua Becker of Becoming Minimalist. I stumbled across his blog years ago and it revolutionized the way I thought about stuff.... or stopped thinking about things I should say.

When you start to rethink the way you think about material goods, you'll feel a huge weight lifted off of your shoulders when you no longer feel guilted into holding onto things and gifts you don’t need.


6. Freelance in an area you're passionate about

Another alternative to a traditional 9-5er is to jump into the gig economy and freelance. Freelance opportunities can be found for entry level to executive level workers. It's all about finding opportunities that fit your needs, skill set, and career goals.

Whether you're in the business of marketing, design, photography, or even homemade goods. There's a way for you to freelance and make a little extra money while gaining more experience and credible references by freelancing.


7. Intern

If you’re looking to escape your 9-5 by entering a new industry, look to gain experience through internship opportunities. Internships at any age or experience level are a great way to enter a new field.


8. Stay on trend with industry news and technology

By keeping up to date with the latest industry news and technology, you'll be able to show your ability to adapt, self-direct and stay up to date with your industry. This is super important if you’re looking to land a remote or tech gig.

Discover what niche news sites exist in your industry. Pull them into a feed through Feedly and read them daily. I also recommend signing up for industry newsletters to read daily.

9. Keep your tech skills up to par to attract remote work opportunities

While continuing to stay on top of your industry, remember to stay up to speed on the general digital tools that are being used in the workplace to keep your productivity up to speed. Some of the popular tools being used in the workplace are:

  • Communication tools: Skype, Slack, and Google Hangouts.
  • Project management software: Teamwork, Asana, and Trello.
  • Calendars: Google Cal, Sunrise, and Calendly.
  • Document management: Dropbox, Evernote, and Google Drive.
  • Coding: Treehouse and Code Academy.
  • Social media management: Hootsuite and Buffer.
  • Email marketing: Mailchimp, Aweber, and Convert Kit.
  • Apps: Postmates, Uber, Lyft, Airbnb.


10. Work for a startup

I've worked for three different startups and I can honestly say this choice was the best decision of my life! Startups are notoriously smaller than most companies which can be great for inexperienced employees to get their hands on a variety of different projects. You'll get to learn more about business, how they operate and how to set and achieve a number of business initiatives.

Employees have greater opportunities to grow with the business and often times are offered equity.


11. Write as much as you can

If I even had the slightest idea how important writing skills are, I probably would have taken more writing courses in college....before dropping out... hehe.

Write daily. Write as much as you can. Write all of your thoughts, goals, dreams, and ideas. It's a form of relaxation and it removes clutter from your mind and stores your greatest ideas where they can be accessed at a moment's notice. If you write a good piece, creative or even informative, turn it into a piece of content for your blog, or better yet, turn it into an eBook that you can sell through your blog.


12. Start and monetize a blog

Start a blog on Wordpress, Squarespace, or Tumblr on a topic that you enjoy. You can blog about a creative passion, sports, or even technology. 

Create a simple content calendar detailing what you'll be posting each month on your blog, create themes and keep holidays, events, and trends in mind when creating content to stay relevant. Spend a few hours a week writing and scheduling your posts in your platform of choice. This will help save you time and assure you stick to a regular posting schedule.

Define your monetization strategy. Decided how you want to make money blogging. Do you plan on using your blog to showcase your writing talents to land freelance opportunities, will you be using it as a lead generation tool to sell art, t-shirts, or other goods? Make sure the proper systems in place to make this possible on your blog, upload your products, and start collecting that cash!

13. Turn your skills, knowledge, passion into a Product That You Can Sell

Take the questions you at get asked the most and turn them into products that you can sell. The options here are endless. You can create: Online courses, Curated communities, Coaching programs, Workshops, Conferences, ebooks and more!


14. Start that business you've always talked about

Hey, no hate. I was you. I understand. If you've been sitting on a business idea now is the time. Start that business. Figure out how you can develop your business around the design of your dream life.

If you currently have a full-time job this is a great thing as you'll have more flexibility to invest in more expensive tools and resources that will help build your businesses and scale effectively and professionally.


15. Convert your current business into an online based business

Whether you're an instructor, a lawyer, or a coach, there are ways to monetize your business online and push your client experience into the cloud. Research or hire someone to do this effectively.


16. Make sure your certs are up to date

There are plenty of untraditional well-paying jobs that simply require you to keep an up to date certification. Look into opportunities to be a bartender, lifeguard, hairdresser, travel agent, or teacher. Discover what certifications and visas are required for you to land that job. Also be sure to keep an up to date passport.

17. Look into work-trade opportunities

Last summer I worked as a dog sitter and had a kick ass opportunity to house sit for an amazing family. In exchange for watching their rather low maintenance dog, I was able to stay in their home for free, was paid for my time, and worked on my freelance assignment.


18. Create projects, portfolio, or a website

If you're looking to grow your portfolio so you can consult, freelance, or work remotely, it's important that you start to build and strengthen your online presence. Create side projects, like a blog or portfolio site. Make sure you have the most up to date samples of your work.


19. Look into remote roles within your current company

If you're happy with your job, but are in need of a shake of routine, look into the opportunity to work remotely through your current company. Organizations are catching on to the desire for work life balance and flexibility. In order to retain top talent, many companies are willing to negotiate alternative working terms if it means they don't lose someone on their team. 


20. Sabbatical year off secured job

There are plenty of people who love their job but feel the need to step away for a bit to refocus and reenergize themselves. If this sounds like you, look into the opportunity to take a sabbatical or extended leave.

21. Take the leap

Sometimes you just have to take a leap of faith and plunge 100% into that dream career or business idea. I can tell you that the biggest thing that held me back from pursuing my entrepreneurial dreams was myself. Let go of your fear.


Bonus Tip: Leverage Your Network

By utilizing tools like Linkedin, email, and social media, you can easily update your network of peers to alert them about your new career changes and job search needs. If you’re new to networking through these social channels, it’s important to understand that you get what you put into them. Take the time to build up a strong rapport and deliver value to your network both on and offline before asking for favors.

  • Did someone in your network get nominated for an award recently? Send them a customized email congratulating them.
  • Is someone in your network looking for a new job? Introduce them to a person hiring for that position.
  • Did someone recently get published online? Share the article on social media.

Taking the time to stay on top of the whereabouts of your network is invaluable. The best part about keeping a strong network is the number of organic inbound leads, opportunities, and introductions that will come your way because of it.

You’ll never truly understand the value of the opportunities
There are plenty of opportunities that could come your way organically through your network once you put in the work to nurture your network, you build rapport, trust, and community and organically funnel the right opportunities.

It’s also important to make sure you’re setting up the right kind of sales funnels for leads that come your way. Create a work with me page, portfolio, canned emails, worksheets, and forms to streamline the process.

This is also another reason why you should keep your site, portfolio, Linkedin, and any industry relevant networking sites up to date on a weekly basis or whenever new content comes out.