I always dreamed of quitting my job. I thought about it when I arrived at work each morning, imagining what my last day would feel like. I thought about it as the morning crawled by at an agonizing pace, even as I refilled my coffee a second, third, and sometimes fourth time to fuel a brain numbed by tedium. I especially thought about it at the end of each day, after my legs were asleep from sitting and I had a precious few hours left in the day to do what I really wanted to do, let alone what I actually needed to do.

Okay, it wasn’t that terrible. But I really wanted to quit my job.

So I did. After almost four years in an industry that wasn’t right for me, I struck out on my own and became a full-time freelancer.

It seemed like the right time. I was newly-pregnant with our first child, and I already had a few years of blogging and freelance experience under my belt. How hard could it be? Plus, if I worked from home, my husband and I wouldn’t have to pay for childcare. Based on what we’d heard from friends who did pay for childcare, that would be a huge, money-saving perk.

Turns out you need a lot of huge, money-saving perks when you quit your job to start a new small business.

My work-at-home experience so far has had its ups and downs. For one thing, I get to determine my daily schedule instead of letting someone else do it for me. I’m saving hundreds of dollars on gas since I’m no longer commuting nearly two hours each day, and I’m steps away from the kitchen, where the coffee pot chugs happily along to refuel me with fresh coffee each hour.

But I’ve made some serious mistakes, too. Mistakes I wish I’d been wiser to before I started working from home.

Here are a few things I wish I’d done before I quit my job (and gave up a rather paltry, but still steady, income):


1 – I wish I’d saved more.

I realize this is one of the golden rules of quitting a job, but as a frugal saver (and personal finance nerd) I thought I’d already saved enough. Not quite. Basic living adds up quickly, and if you’re not prepared to cover your expenses somehow, it gets overwhelming. Fast.

2 – I wish I’d developed a more detailed plan.

Don’t get me wrong; I had a plan. But it wasn’t nearly detailed enough. I needed to write a plan and adapt it to a manageable timeline so I had specific goals to work toward each day, week, and month instead of waking up every morning and floundering as I multitasked my way into exhaustion.

3 – I wish I’d set a daily schedule from the start.

Speaking of detailed plans… Working from home is a dream for those of us who crave freedom. If we don’t want to be chained to our desks all day, we don’t have to be. However, unless you’re inherently self-disciplined, it’s easy to let that daily freedom make you lax in your work. I’ve tried scheduling my day a few different ways so far, but I’m still looking for the perfect fit. When my daughter was born several months ago, my scheduling took on an entirely new dimension!

4 – I wish I’d started earlier.

I began laying the foundation for my blogging and writing career while I still had my day job. But I approached it far too casually. I wrote when I felt like it, not every single day (like I should have). I wrote, blogged, and networked inconsistently instead of starting small and building up steady momentum. I let the comfort of my day job keep me from moving forward consistently. It’s easy to do. But if you have a job you’d like to get out of, start working toward your goals now instead of waiting until that glorious quitting day you’ve been dreaming about.

5 – I wish I hadn’t let fear hold me back.

Reaching out to other entrepreneurs and bloggers is intimidating, especially for an introvert like me. I consider how nice it would be to work with writers and small business owners I admire, but then I imagine how much all of those “no”s might sting.

The problem with shrinking back in fear like that is that I’m making assumptions about others, assumptions that are most likely wrong. Sure, I’ll get rejected along the way. All writers do. (That’s just one of the perks of the job.) But most people are more than happy to not only hear me out, but help me out. There have been too many moments when I let my fear of rejection keep me from reaching out to someone who might have been a great connection.

Working from home can shake your nerves. It can make you question your professional purpose and leave you feeling more financially insecure than ever.

But speaking from experience, you learn a lot more in a vastly-condensed amount of time. You learn about your industry, yourself, and your highest priorities. Plus, the potential payoff is so much larger than settling for a job that isn’t right for you. And not just financially — personally, too.

Interested in learning from more of my mistakes? Ink Blots & Happy Thoughts: 20 Lessons Learned in My First Year of Freelance Writing is currently available on Amazon.

Have a friend or colleague who’s ready to plunge into a new small business? Do them a favor and share this article with them using the social buttons.

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Meghan Bliss