How To Quit Your 9-5, Work Remotely, or Work For Yourself


If you’re looking to break free of the office 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.



Sign up for Flexjobs to search through vetted job listings

I think the hardest part of getting started working remotely is figuring out where to find legit work. When I first started looking for ways to make money online, I thought I'd have to be on alert for scammers and low-paying gigs at all times.

It turns out, there are a number of high quality, vetted remote job boards out there. If you're just getting started working from home, I highly recommend giving Flexjobs a try. Their job boards are super organized and advanced and they do an incredible job curating listings.

Wondering if they'll have an opportunity that fits your career and personal needs? Here are a few industries they post jobs for.

  • Account Management

  • Animals

  • Art

  • Accounting

  • Administrative

  • Advertising 

  • Business Development

  • Creative

  • Computer Science

  • Customer Service

  • Design

  • Data Entry

  • Editing

  • E-commerce

  • Education

  • Engineering

  • Finance

  • IT

  • Public Relations

  • Project Management

  • Recruiting

  • Transcription

  • Wildlife

  • Writing

You can also see a full list of their job categories here.


Clarify what makes you happy and unhappy at work

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

Sit down in a quiet space alone and journal. 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?

  • In a perfect world, how would you manage your stress?

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

Another exercise you may want to consider is thinking about the reality of what it's like working from home. Research other blogs on the pros, cons, and other's experiences.

Also, consider some of the logistics of working from home:

  • Are you organized in the environment you'll be working in from home?

  • Do you have a comfortable work desk and chair?

  • Do you have the right technology to work from home?

  • How loud is your home during the day?

  • What is your wifi situation like?

  • Are you self-disciplined?

  • Are you self-motivated?

  • Are you organized with your work documents?

  • Are you able to push a project forward from start to finish without being followed or managed?


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.


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 will you start?

  • 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 day to day life temporarily to achieve this sooner?

  • What are some things you'll need to sacrifice to get there?

  • What are the risks of leaving your job?

  • How will this affect your long-term 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.


Audit your finances like crazy and budget for your new career, lifestyle, and income

Speaking of plans, it's important to discuss and plan how quitting your job, freelancing, or starting a business may affect your finances. Before quitting my full-time job to freelance, I tested it out for a few months by renting out my apartment, traveling, and picking up clients. Doing this allowed me the freedom of knowing at any time I could go back to my apartment in Manhattan, get a full-time job, and go back to my old life - if that's what I wanted.

Before switching up your career path, it's important to take a hard and close look at your finances. Ask yourself the following:

  • 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?

  • How exactly will you reach this income goal monthly?

  • Are there things you want to omit from your budget to achieve this goal?

  • Are you prepared for a rainy day or if things don't work out?

  • Will you keep or downsize your apartment?


Fix your money mindset by reading No BS Wealth Attraction for Entrepreneurs by Dan Kennedy

One of the best books I've ever been recommended as a freelancer and business owner is No BS Wealth Attraction for Entrepreneurs. If you're looking to reshape your mindset when it comes to money or are entering the freelance or solo business world, this one is worth your time. It talks about the struggles many people face when it comes to money, and simple effective ways to change your mindset if you're done with feeling stuck when it comes to money.

It may not sound like the most exciting read, but it's quick and worth it. No pun intended.



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. 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.

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?

  • Have you accumulated a surplus of things that no longer bring value to your life?

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.


Freelance in a new industry that you're passionate or already knowledgeable 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.

Many people tend to think they need to develop a completely new skill set just to take advantage of flexible work or to earn more money. Sometimes it's better to focus on the skills and experience you already have and how you can leverage them in demand jobs in today's economy.



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.


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.



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.


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.


Get paid to write for major publications and grow your brand credibility

Write as much as you can to improve your craft and pitch your best work to major sites daily. To get started, write down your current thoughts, goals, dreams, and ideas. Mind map in a journal brainstorming topic ideas. I highly recommend getting into the habit of writing by hand, especially if you enjoy writing in the morning. It's an easier way for me to avoid distractions and get my best work done.

If you notice your work performs better when you write about certain topics vs others, consider creating an info product or physical product around the topic. You could also consider writing similar content for your personal blog to drive more traffic to your site.

To pitch an article, go to your site of choice and find the contact information of the editor of the section you want to write for and email them or look for the general submissions or contact form.


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!



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:

  • a print or digital book

  • live online seminars

  • in person workshops

  • online courses

  • curated membership communities

  • coaching programs

  • art

  • t-shirts and other wearables

  • tech

  • food

The possibilities here are seriously endless.

To create an online store you can use:

  • Shopify

  • Squarespace


Start that business you've always talked about

Hey, no judgment! I understand - as I've been there myself. If you've been sitting on a business idea now is the time. Start that business, you don't necessarily need to quit your day job to do it. 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.

  • Set aside a date and time to get organized and create a game plan for your business

  • Stick to your plan and take daily action, you'd be surprised by how far 30 minutes a day can go


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.

You can drive leads and clients your way through:

  • a website

  • writing for other websites

  • being features on other sites

  • Instagram

  • Twitter

  • podcasts

  • email

  • webinars

Research or hire someone to do this effectively.


Make sure your certifications and passports are up to date

There are plenty of untraditional well-paying jobs that simply require you to keep an up to date certification. Discover what certifications and visas are required for you to land unique travel jobs. Also be sure to keep an up to date passport.

A few jobs where certifications are handy:

  • bartender

  • lifeguard

  • hairdresser

  • travel agent

  • teacher

  • travel nurse

  • house sitter

  • dog sitter

  • baby sitter


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.


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 on it at all times.


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. 


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.


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.


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.


Career, LifestyleDestiny Lalane