This post kicks off my Blogtober 2019 experience, and it’s also rather more personal than my usual content. TL;DR – Blogtober is an annual month-long content creation challenge that takes place in, you guessed it, October. The objective? Commit to creating fresh new content every day for a month. Challenge accepted. If you’re participating in Blogtober, feel free to connect with me on Twitter 👉 @aspiretowander
When I was a young, innocent, prematurely jaded high school freshman, I started a bespoke handmade jewelry business, hustling special orders and premade prototypes to my enthusiastic customers. I hustled, and dammit, I did so efficiently. I sold my wares to teachers, handbag-loving peers, and eager boyfriends looking for a present within their still-on-allowance budgets — but would still adequately communicate their affections.
Within one month, overwhelmed and bored of Beadalon, briolettes, and needlenose pliers, I shut it all down. I refunded all outstanding orders and wiped my hands clean of this lemonade stand.
But my short-lived fashion accessories empire was not my first foray into entrepreneurship, nor would it be my last. An entire lifetime later, now in my early 30s, I’ve started and stopped more micro-business ventures than I can remember. So far, nothing has stuck— at least nothing so sticky, sustainable, and profitable as to compel me to quit my day job. Note: I do love my job though, so prying me away from the company is a tall order indeed.
The starting, doing, and subsequent stopping is a cycle I’m familiar with, and it doesn’t feel good. The evidence is clear. I need to continue working on:
- the fine art of conquering goals with ease
- building good and lasting habits
- funneling my passions into something profitable and sustainable for my family

And there’s that dang imposter syndrome again.
The last item on the list feels like alchemy, at least when it comes to my side hustles! Day job responsibilities, though? It’s basically like printing money— for the company that is. 😅
Basically, without a system to keep me accountable, I am easily thrown off course, discouraged by none other than that little voice in my head.
Blogtober Mission: 2019
That entrepreneurial spirit and drive that’s motivated me to try oh so many things? It lives on and visits often, whispering sweet nothings into my ear and encouraging me to dream and do beyond the obvious. Beyond the safe.
The reality of it: While I tend to adulting things, I build these side projects. I’ll create and ideate, sometimes haphazardly and often without a clear outcome in mind. I squirrel away free moments and borrow sleep from late nights just to work on my projects, albeit not always with a roadmap or an overarching objective in sight.
I’m going to change that. I owe it to myself and to my family to make sure I’m spending my time effectively— side hustle or not.
I’m going to lean on this year’s collective Blogtober movement to keep myself accountable for three things I struggle with in my side-hustle entrepreneur journey:
Setting S.M.A.R.T. goals
As an active participant in Blogtober 2019, I’m committing to publishing no less than 31 fresh and substantial blog posts and articles— one for each day of the month. Yup, even on Halloween.
Building sustainable habits
During Blogtober, I’m committing to publishing one blog post or article each day. I’ve got a pretty massive list of topics outlined already, and the list just gets longer and longer. It’s time to put a dent in it.

Iterating on my Passion to Profit path
The goal here is clarity. Real talk: this last item is the most complicated, and honestly? The scariest. Details TBD.
Hey there Blogtober. What’s good?
Are you participating in Blogtober 2019? Let’s connect! Drop your link below, or ping me on Twitter.
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