So, You Want to Quit Your Job and Start a Blog?
Portrait Taken in Milwaukee Wisconsin by Jessi Esselman
Photo by Jessi Esselman

There’s quitting your job, there’s starting a blog, and then… there’s quitting your job to start a blog (or to freelance, create content, etc). In December of 2018, I left my first full-time post-grad job (to be fair, it was an internship) with nothing but a brand new blog and a full list of new year’s resolutions. Sounds promising, right? Yeah, my dad’s thoughts exactly.

At the time, The Wisconsinista was only about six months old. It had accrued a bit of an Instagram following since its debut in June, but had never seen the likes of a paid collaboration or sponsored post. I purchased my website’s domain on January 1st, transferred all the content from my free WordPress site over to it, and had zero page views to start out the year. I didn’t have a job or other incoming cash flow, but my goal was to take the entire year off of “work.” So how the heck did I do it?!

Look, I promise to be 100% real with you guys, because if this is something you really want to try, you have to know how other people really made it work, even if that means learning their situation is more complex than it appears at first glance. You can totally peace out now if reading anything besides a zero-to-hero ground roots success story isn’t for you. I didn’t do this on my own and I’m not above admitting it.


Arguably the most important part of this whole thing, right? In my experience, you need solid financial savings (relative term; you can define how much that is) to fully embrace a season of freedom. I feel like I read/see clickbait Facebook ads all the time about people who quit their job with no savings + debt and found success without a 9-5. Their stories may be true, but that situation is not optimal. I know I wouldn’t risk it with those chances. So how did I make it work?

I’ve never felt comfortable sharing this next fact before (and I still don’t), but honesty is of utmost importance if I want to thoroughly discuss this topic with you: I don’t have any debt. I’ve never had any debt. Not from college, credit cards, car payments – none of it. I have my parents and scholarships to thank for a good portion of my college funding, but I took other steps, too. I went to a public, in-state university less than an hour from my childhood home. I lived at that childhood home for portions of college. I lived with roommates for the other portions.

I worked, too. Not constantly. Not when the workload would tank my grades and threaten the need to re-take a class. I did anything I could to pass my classes the first time, take classes that met as many GERs as possible, and graduate as early as I could. That alone saved me thousands. I worked almost full-time every summer and part-time as the school year allowed. Most importantly, that money I earned? I didn’t spend it.

In the Yellow

Okay, that was clickbaity. I did spend some of the money I earned; I spent a lot of it. I didn’t, however, spend virtually any of it on things I didn’t absolutely need. My number one rule that I always jokingly tell people is never to pay for water, since it is available for free at bubblers (read: water fountains) virtually anywhere and all you need is a reusable water bottle to capitalize on it. The bigger picture I use that tidbit to emphasize is that a little planning can go a long way in the money-saving game.

I read somewhere that there are two ways to accumulate more money: 1) work more and 2) spend less. If you want to take some time off of work, the latter will be your focus. There seems to be a growing acceptance for taking time off these days, with praise given for gap years spent traveling the world, but no one seems to talk about how much longer you can get away with not working if you don’t spend all your money on vacations. If you literally just take some time to stay at home and grind away on your blog instead. Or brand. Or practicing witchcraft. Whatever you want. I’m not here to judge!

This idea of living neutrally (not saving but not really spending), or “in the yellow,” isn’t in any Pinterest pin I’ve seen while searching for blog posts about time off. For as much as we spend time dreaming about days off and complaining about our packed schedules, the idea of opting not to work simply to rest isn’t esteemed as an option somehow. Whatever. We’ll make it trendy. Live neutrally and feel free to say no to anything that isn’t an investment in your future.

Along the Milwaukee River in Downtown Milwaukee Wisconsin by Garrett Black
Photo by Garrett Black

Work for Fun

While I’ve never regretted my decision to leave that first job (internship) in my field of study, I did want to get out of the house a bit once I’d been totally off for over a month. For the sole reason that I truly wanted to, I decided to resume my part-time seasonal post as the office manager with a local boat tour company for the 2019 season (March-September).

Just because you want to steer clear from a mundane, corporate position for the year doesn’t mean you can’t pursue a job as a hobby during your break. If it’s a job that you think is fun, why not give it a try? Even if the money isn’t great, it’s still way better than the spotty checks you may or may not get from your new blog. It is a great way to save for equipment you might want (I’m currently in the market for a good vlogging camera) and may even give you something to write about!

You might also learn in the process, like I did, that working a fun job part-time and blogging part-time is a good balance. Your in-person job will give you a reason to get out of the house and make friends in a work environment that is much less stressful than a corporate one. It will also keep you from getting sick or bored of blogging and thus keep you motivated to stick with it long-term!

Be Intentional

Lastly, it’s important to realize that making money blogging is not an overnight process. Just like with any other career path, the first step is to get the proper education or training. You can opt to splurge on a blogging course or just do research and train yourself, but recognize that both options are way cheaper than paying college tuition, so it’s a pretty decent investment in yourself either way.

Your “training” may also take the form of watching YouTube videos from industry experts, figuring out how to design a website and blog, writing guest posts on more established blogs for the exposure, or accepting product from a company as compensation in exchange for a sponsored social media or blog post. These will all build your portfolio and grow your audience so that you can eventually pitch yourself as a great candidate for a paid partnership.

This does not mean, however, that you should accept every collaboration opportunity that comes your way. Be intentional about your partnerships and realize that developing a consistent and honest personal brand is also a critical part of your training. Stay away from products you don’t already use or believe in, as well as companies that expect spammy amounts of sponsored content in exchange for “gifts” alone. They’re not really gifts anyway when you get them in exchange for work – they’re compensation!

How to Quit Your Job and Start a Blog Pinterest Pin

Ready to start blogging and take a leap of faith in your career? It can be scary, but preparation is key. To get you started, here are some travel blogger pro tips to help you travel more for less. Now, it’s time to start crushing your goals and living your dreams!

This Post Has 2 Comments

  1. Chelsey! Great post. I recently left the 9-5 to concentrate on my outdoor adventure events company. Very scary but I’m totally in agreement with the make / spend dynamic and how the adjustments you make can dictate your success.

    1. Cindy,

      Thanks so much for your comment! I’m definitely learning that it takes risk and hustle to manifest lifelong dreams, but it can be so worthwhile. Best wishes for you and your company!

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