Jessica Williams's Blog

July 17, 2025

Automate: Simple Systems That Lighten Your Side Hustle Load

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Some days, it’s just me, my side hustle, and a mountain of to-dos.

That’s why I’ve learned to lean on little automations. Not the fancy kind, but the “thank you, tiny robot friend” kind. The ones that take something off my plate quietly, in the background.

This is the kickoff to my Side Hustle A to Z series: a mini project where I’m sharing small, doable tips for building your side hustle in a way that supports your life too.

No overwhelm. No all-or-nothing energy. Just one little shift at a time.

And we’re starting with one of my favorites:

A is for Automate.

Why automate?

Because honestly? I’m tired. 😂

I’m juggling a job, caregiving, and building something of my own — and I don’t have energy to waste doing the same task over and over again when a tiny system could do it for me.

Think:
🌀 Set it and forget it.
🧠 Save your brain for the good stuff.
💆🏾‍♀️ Protect your energy like it’s sacred (because it is).

Some automations I love:🗓 TidyCal lets people book time with me without the email back-and-forth. I can set my availability once and let the system handle the rest.🏥 Amazon Subscribe & Save delivers Ensure for my grandma every other week (along with other household staples). Bonus: Alexa reminds me when stuff’s running low.📅 Buffer lets me queue up LinkedIn posts when I’m in the mood to write, so they go out while I’m working, caregiving, or lying in bed watching Sweet Magnolias.💸 Autopay for bills. Because who has time to remember due dates anymore?Related: you can  automate savings  + prescription refills too!⌨ Text replacement on my phone and laptop. When I type zadd, it fills in my full address. Magic.

These might seem small, but together? They make me feel like I’ve got a tiny team working behind the scenes, even when it’s just me and my phone at 9:43 p.m.

Not sure where to start?

Here’s a tiny automation you can try today:

➡ Set up text replacement on your phone for your email, address, or favorite hashtags.
(iPhone users: here’s a 43-second video on how to do it)

Takes 2 minutes. Saves you dozens over time.

Or ask yourself this:

What am I doing over and over again that makes me whisper,
“There has to be a better way”?

That’s your automation cue.

You don’t have to automate everything.
But even one small system can help you reclaim your time, energy, and a little peace.

And that’s the point of all of this, isn’t it?

Not just building a side hustle, but building a life that feels more you.

So if you’ve been feeling behind or overwhelmed or like it’s all too much…
Let the robots help. 🤖

Your future self will thank you.

💬 What would you love to automate?

Got a favorite time-saver you swear by? Something you’d like to automate but haven’t figured out yet?

Drop a comment and let’s swap ideas, because sometimes the best tips come from fellow side hustlers figuring it out in real-time.

P.S. This is part of the Side Hustler’s A to Z Survival Guide series: one small shift each week to help you grow your side hustle in a way that’s sustainable, joyful, and real.

Next up: B is for Breaks. Because… we all need them
.

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Published on July 17, 2025 18:40

The Side Hustler’s A to Z Survival Guide

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Side hustling while living your life? Whew. It’s a lot.

Welcome to the Side Hustler’s A to Z Survival Guide: a cozy little series where each letter of the alphabet gets its own tip to help you build a side hustle without burning out.

This is not your “wake up at 5 a.m. and do 12 things before breakfast” kind of vibe.
(Because seriously, who has that kind of time?)

It’s for the tired, the busy, the start-and-stoppers.
The folks balancing a full-time job, caregiving, errands, and still trying to make space for something of their own.

Each week (ish), I’ll share one small shift to try. No pressure, no all-or-nothing thinking, just doable ideas you can try in the margins.

Start where you are. Come back when you need a boost.

Try what works. Skip what doesn’t.

Let’s build something that fits your life.

✏ The A to Z Lineup (so far…)

🔁 A is for Automate
Tiny systems that take tasks off your plate (thank you, robot friends)

🧘🏾‍♀️ B is for Breaks
Rest isn’t a reward. It’s the rhythm that keeps you going

📝 C is for… (coming soon!)
(Bookmark this page — new letters added weekly-ish!)

Want these by email?

I send each new letter through my #jesspicks newsletter, along with curated tools, personal notes, and a little encouragement for the week ahead. 💌

P.S. Got a favorite tool, habit, or mindset shift that’s helped your side hustle feel more doable? Tell me about it! I’m always collecting gems to add to future letters.

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Published on July 17, 2025 18:38

April 15, 2025

Read This Before You Take Your Side Hustle Full-Time

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I saw a post the other day that said:

“Your side hustle is your escape plan.”

And while that’s true for some, it's not the only way.

Maybe you’re in a toxic job (been there).
Maybe you’re looking for more freedom.
Maybe you’ve always dreamed of working for yourself.

But that wasn’t my story, and it might not be yours either.

For a long time, I thought my side hustle was just the first step:
Start small. Grow big. Quit your job. Live the dream.

That’s how it goes right?

But then life happened. I found a job I really loved.
I became a caregiver.
I tried full-time entrepreneurship. Didn’t love it.

Turns out, I like:

Steady incomeHealth insurance (and PTO is great!)The stability that lets me care for myself and the people I love

My side hustle stopped being an “exit strategy” and became a creative outlet—a space to explore, experiment, and build something meaningful without the fear of losing everything.

What changed?

I realized that the ”all-or-nothing” approach wasn’t for me.
I used to believe full-time was the only path, that I wasn’t a ”real” entrepreneur unless I went all in. But when I ran my business full-time, I didn't love:

The constant worry about where the next dollar was coming fromSaying “yes” to everything just to pay the billsThe overwhelming pressure

Could that change someday? Maybe. But right now, I’m choosing to keep my business as a side hustle—on purpose.

Because it gives me:

Freedom and stability.The ability to say no to what doesn’t feel right.The space to grow at my own pace, with room to rest and recharge.

And I’m allowed to honor that.

Let’s be real: Going full-time isn’t always as glamorous as it looks on social media.

Here’s what people often leave out:

You trade stability for a different kind of stress.That passion project can start to feel like a burden.It can be isolating and overwhelming.

Some folks thrive in that “leap and the net will appear” energy.
Me? It’s not my jam.

What if your side hustle is enough?

Not everything has to go big. (And yes – going home is absolutely valid)
It's okay to love your job.
There's more than one way to be an entrepreneur.

Sometimes the most powerful thing you can do is say is, “I’m building this in a way that works for me.

Maybe that means:

Being present for your family.Prioritizing your health and self-care.Saying no to clients that aren't aligned. (all money isn’t good money)Having fun with your work again.What do you want?

Before you take that leap, ask yourself:

What’s really driving this decision?Do I want to leave my job—or do I feel like I should?What kind of stability do I need right now?What would make me feel truly supported?

You’re allowed to grow slow. You’re allowed to keep your job. You’re allowed to build something on the side. You’re allowed to say, “This is enough for me.”

That doesn’t make you less of an entrepreneur. Or less committed. It puts you in control.

Because the truth is: The best business is the one that fits your life—not the other way around.

There’s no one-size-fits-all path.
Are you building something on the side? Full-time? Somewhere in between?
I’d love to hear what your journey looks like.

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Published on April 15, 2025 11:49

March 14, 2025

The 5-Minute Side Hustle Boost: Practical Tips for Busy Entrepreneurs

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When Life Gets in the Way, Take 5!

Life’s busy, right? Between your day job, personal life, and what can seem like a neverending list of responsibilities, it's easy to feel like your side hustle always comes last. But what if I told you that five minutes could make a difference? Yes, even just 5 minutes!

I was inspired by Chris Guillebeau’s recent newsletter about the 5-Minute To-Do List—a concept where you keep a list of small tasks that can be knocked out in 5 minutes or less. It’s perfect for those moments when you have a tiny pocket of time and want to take advantage without feeling overwhelmed.

As someone who is constantly juggling a full-time job, caregiving for my grandmother, and my business, I've learned that small pockets of time are gold. So, as I continued to develop my own 5-minute list, I figured “Why not create a version of this specifically for other jugglers like myself?”

This list is designed to help you “Take 5” throughout your day and turn small moments into meaningful progress on your side hustle.

For Motivation (when you need a quick boost)Write down one tiny win from the past week (no matter how small)Create a folder of screenshots with positive customer feedback to revisit when you need a smile Listen to some upbeat music to get energizedMake a quick list of 3 reasons why you started your side hustle (or review that list for a reminder to keep going)Record a voice note hyping yourself up (or if you’re a ChatGPT fan, ask it to describe you as if it were your drunk bestie. Trust me, it’s fun!)Find and save an inspirational quote that resonates with your current seasonGrab one of my mini pep talks!For Prioritizing Tasks (when you feel overwhelmed)Make a visual schedule to see where you can fit in side hustle timeDo a brain dump of everything that’s on your mind, then circle the ONE thing that matters mostChoose one task to finish today (even if it’s a small part of a bigger project)Reschedule tasks that don’t need to be done right nowCreate a “Done” list to celebrate the progress you’ve made.Think through a typical day and figure out what times you are most productive.  Block out 15 minutes of that slot for side hustle tasks tomorrow.For Working at Your Own Pace (when you feel behind)Give yourself permission to take breaks and recharge. Tomorrow is another day.Take a photo of your workspace/progress to document your journey (this becomes a powerful reminder of how far you've come)Unfollow or unsubscribe from accounts or people that make you feel behindWrite down one reason your current pace is right for you and your circumstancesAsk for more time on a deadline that’s causing you stress (most people are more understanding than you'd expect)Create a “not doing right now” list — a parking lot for your ideas so you don't forget themFor Focusing on What Matters (when time is limited)Help Future You by asking: “What can I do now to make my life easier later?” Figure out your most important task that needs to get done today and commit to working on it for 5 minutesCheck your calendar and block out two 15-minute slots of “side hustle time” this weekPick one task that you can batch with similar tasks to save time (e.g phone calls, social media posts)Look at your to-do list and see if there is something you can delegate (e.g. could you order dinner or ask a friend to handle an errand?)Set a timer, clear out distractions, and do just one of these 5-minute activitiesFor Marketing without Overwhelm (when you need visibility)Set up a Google Alert for your industry keywords so you can stay informedShare one quick tip, insight, or win on your preferred platformMake a list of 3 simple ways people can work with you (write it on a post-it note and stick it on your laptop)Reach out to 1-2 folks that you could collaborate withRecord a quick voice note with a content idea to work on laterCreate a simple email signature that promotes your business – include your services and website link (it's a simple way to market without directly marketing)  Bonus: it works even when you’re not directly marketing!)Why This Approach Works for Side Hustlers

The beauty of these 5-minute tasks isn't just that they're quick. It's that they help you:

Maintain momentum even during busy seasonsBreak through some of that mind gunk when you're feeling stuckBuild consistency without needing big chunks of timeReduce overwhelm by focusing on just one small actionCreate progress that motivates you to keep goingHow to Make “Take 5” Work for YouStart with your biggest pain point. Feeling unmotivated? “Take 5” to boost your mood. Overwhelmed by marketing? “Take 5” to make it easier.Keep this list somewhere visible or create your own version of this list on your phone.Don't try to do everything. Pick just ONE thing that feels right for today.Track your 5-minute wins in a simple journal or notes app. After a month, you'll be amazed at how much you've accomplished.

Remember, slow progress is still progress. Every 5-minute action adds up to meaningful momentum over time.

Think about what’s weighing on you right now or what your side hustle needs most. Which of these tasks would help YOU move forward today? What would you add?

Let me know in the comments!

Want more side hustle support that fits your busy life? Sign up for #jesspicks where I share practical advice for building a business while keeping your day job.

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Published on March 14, 2025 19:56

May 28, 2024

3 Side Hustle Strategies Inspired by the Minions (They’re Not Just Cute!)

Juggling a day job with a side hustle can feel challenging at times, right? You're pouring your heart into this passion project (or that extra income stream), but there never seem to be enough hours in the day. Before you throw your Macbook out of the window, let's see if we can take some inspiration from the Minions.

Remember that first time you saw Despicable Me and fell in love with the Minions? Me too! Theyre more than just cute characters, though. As I was re-watching Minions the other day (because, lets be honest, they never get old!), I realized these little guys have some surprisingly big lessons for us.

1. Team up.

Remember when Gru’s moon-stealing plans were on hold because he had no money? Then, what happened? A tiny Minion offered up his piggy bank (in the most adorable way, of course!), and suddenly, the whole Minion crew followed suit. It was an awww-worthy moment, yet it gave Gru the motivation to keep going.

The Side Hustle Takeaway: Connect with other side hustlers online or in your community. Bounce ideas off each other, share resources, and celebrate each others wins. Sometimes, all it takes is one person to know youre not alone. Building a support system can make all the difference in your side hustle journey.

What online communities or groups have helped you connect with other side hustlers?

2. What's your “banana”?

We all know the Minions go bananas for, well, bananas! To them, bananas = happiness. Whats your side hustles “banana”? Is it the creative freedom of pursuing a passion project? The satisfaction of building something from the ground up? Maybe its the stability you feel from diversifying your income streams. My banana (or my why) is about letting folks know that they can build a business in a way that works for them, and there is not a one-size-fits-all scenario.

The Side Hustle Takeaway: Identifying the why behind your side hustle is essential. When the going gets tough (and it will!), remembering your “banana” will keep you motivated and focused on your goals.

What is the driving force behind YOUR side hustle? Share your “banana” in the comments!

3. Embrace experiments and adventure.

The Minions are always up for anything, even if it lands them in some tricky situations (remember hitching a ride with bank robbers?). But heres the thing: they always make the best out of every situation. Even getting thrown in the dungeon becomes a fun adventure for them!

The Side Hustle Takeaway: The side hustle path is rarely smooth sailing. There will be unexpected challenges and setbacks. The key? Embrace the unexpected, learn from your mistakes, and find the silver linings. Remember, sometimes the best detours lead to amazing discoveries.

Building a side hustle alongside your day job is not easy, but the rewards are totally worth it! Keep these lessons from our favorite yellow friends in mind as you navigate the highs (and sometimes lows) on this journey.

Now it’s your turn! What unexpected lessons have you learned on your side hustle journey? Share your experiences and tips in the comments below – lets build a supportive side hustle community together!

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Published on May 28, 2024 04:38

May 20, 2024

Side Hustle Overwhelm? Me Too. Let’s Fix That (In 30 Minutes, Seriously)

Let’s face it, juggling a job, a business, and life can feel overwhelming sometimes. That can look like:

You could feel stressed out.You could be procrastinating on a task for whatever reason.You feel stuck and unsure of what your next steps should be.You’re just tired.You're ready to crawl under the covers and hide from the world for a day or three.

Not to mention the dozens of emotional support Internet tabs you have open (31 for me!) and the neverending to-do list.

Sound familiar?  

But here’s the good news: we can gain control of the chaos in just 30 minutes. Yes, you read that right, 30 minutes!

So, grab a coffee (or your beverage of choice, because #adulting) and let's break down this overwhelm.

Part 1: Identify What’s Causing Your Overwhelm (10 Minutes)

Overwhelm doesn’t always announce itself. Sometimes, it sneaks in, and you just feel some kind of way – stuck, stressed, or simply exhausted.

But once you know you feel that way, we want to get clear on what’s causing it. Here’s how:

Brain Dump Time! Grab a pen and paper (or your phone, whatever is easiest for you). Set a timer for 5 minutes and write down EVERYTHING swirling in your mind.  Don’t think; just write – tasks, worries, fears, ideas. The point is to get it all out of your head so we can start making sense of it.
Review: After 5 minutes, close your eyes, take a few deep breaths, and review your list. Are there any recurring themes? Do specific tasks make you take a deep breath?  Or make you wonder how in the world you can get them done? Those could be the ones triggering your overwhelm.

Real Talk: It's okay if your list looks like a jumbled mess. The point is to get it all out of your head and onto paper (or screen) so we can start making sense of it.

Part 2: Prioritize your To-Do List (15 Minutes)

Now we know what we are working with.

Prioritize: Grab your brain dump list and a fresh sheet of paper. Set a timer for 5 minutes. Scan your list and identify 2 to 3 urgent tasks for your side hustle this week. These are your “Top Priority Tasks.” Think of them as the VIPs of your to-do list.
Now, let’s baby-step this business: Let’s make those top priorities feel less…big. For each task, ask yourself: “What’s the smallest, most actionable step I can take right now to move this forward?” This step should take 15 minutes or less to complete. Write down this first baby step next to its corresponding task. Repeat this for each of your VIPs.

💡 Feeling overwhelmed by even the baby step? Break it down even more! Can you identify a 5-minute action item within that first step? Remember, progress is the goal here. Not perfection.

Part 3: Celebrate (5 Minutes)

Once you’ve identified a baby step for each of your top 3 tasks, give yourself a high-five and spread some virtual confetti. 🎉

You’ve identified what’s causing you to be overwhelmed, prioritized your side hustle tasks, and created a to-do list with actionable, bite-sized steps. And all in 30 minutes.

Know what that is? A HUGE accomplishment! 🏆

Bonus Tip: Take a moment to schedule these baby steps into your calendar. Block out three 15-minute sessions to make progress on those VIP tasks over the next week.  Let me know how it goes.

Focus on those small, achievable steps. Consistent action, no matter how small, will move you closer to your side hustle goals. Remember, it's about progress and building momentum. Keep swimming.

Share your biggest side hustle overwhelm trigger in the comments below! Let's manage this together, one baby step (and cup of coffee) at a time. We’ve got this!

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Published on May 20, 2024 06:49

November 20, 2023

The Best-Kept Productivity Secrets: Batching Tasks, Timers, and Saying No

Do you feel you constantly juggle too many tasks and never finish anything? You’re not alone. This blog post will discuss some of the best-kept productivity secrets, including batching tasks, using timers, and saying no. I’ll also share tips on ensuring you live a life that fills your soul.

Say “No”

It’s also important to remember that you can’t do everything. Sometimes, you have to say no to focus on what’s important. I’ve been working on this lately, and it’s been beneficial. One of my friends said, “Sometimes living a life of yes means saying no.” And I think that’s such a good rule of thumb.

Related: 4 Tips for Saying No Without Feeling Guilty

Batch Similar Tasks Together

One of the best ways to increase productivity is to batch similar tasks together. This means grouping similar tasks and completing them all at once. For example, if you need to make some phone calls, do all your calls in one sitting rather than spread out throughout the day. Batching saves you time and energy because you’re not constantly switching tasks, and helps you be more efficient.

Do Things That Fill Up Your Cup

Make sure you’re doing things that make you happy and help you recharge. I’m still working on this, but I know it’s essential. For example, dancing brings me joy, so I try to dance every day, even just for a few minutes.

Step Out of Your Comfort Zone

Take steps out of your comfort zone. I’m not saying that you need to parachute out of a plane (because I will not be doing that. Also soo afraid of heights), but do something that stretches you a little bit. Then, even if the experience sucks, you will have learned something that can serve you in the future.

Use Timers

Another excellent productivity secret is using timers. They help you stay focused on a task and avoid getting side-tracked. For example, if you’re working on a project that requires your full attention, set a timer for 30 minutes and work on the project until the timer goes off. Then, take a break for a few minutes before continuing with your work.

Create Your Own Definition of Success

And finally, success may look different to you, and that’s OK. A couple of years ago, I was so busy with my day job that I barely had time for my business. I wanted to do something consistently for my audience to provide value. That’s how the idea for my #jesspicks newsletter was born. I feel successful as long as I get an issue out every week. It doesn’t matter if it goes to 50 people or 500 people. What matters is that I’m doing something that I love and that helps others.

So there you have it, my friends: a few of my best-kept productivity secrets. Do you have any to share? I’d love to hear them!

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Published on November 20, 2023 07:20

November 18, 2023

10 Productivity Tips for Working from Home

An oldie but goodie interview with Adam Grant. While the focus is on working from home, there are some great productivity tips as well, like these:

Get creative outside of work. Make time for a hobby – something you can do purely for the joy and recharge properties. Mine are dancing, reading, and jigsaw puzzles.Focus on attention management versus time management.

“You can't control the number of hours you have in the day,” says Grant. “All you can do is try to focus as much of your energy as possible on the people and the projects that really matter to you.”

Another good point that Adam mentioned that made me scratch my head a bit is that your most creative energy is probably at a different time of day from when you’re most productive. 🤯

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Published on November 18, 2023 07:09

November 11, 2023

30 Places to Find New Clients

Ellen shared 30 places to find new clients. For me, just thinking about this past year, this is where mine have come from:

#jesspicksSocial Media – specifically LinkedIn, Instagram, Twitter, FacebookMy weekly dance classReferrals from existing clients

Also, my coworking space is a speaking client!

Where have you found your clients? What else would you add to the list?

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Published on November 11, 2023 07:08

November 7, 2023

Side Hustlers: Discover Your Most Productive Time of Day

Most productivity articles recommend that we wake up early, establish a morning routine, and get moving. While these tips can be helpful, it’s essential to understand that such advice may not work for everyone.

There isn’t a “one-size-fits-all” solution to productivity, as the right time for you may vary. For instance, waking up early may not be the best time to get work done if you don’t operate at your highest energy level.

Some folks may do their best work in the afternoon, while others may feel energized late at night. It’s all about discovering the time when you’re most productive and using it to optimize your day.

As a morning person, I do my best work between 7:30 a.m. and noon. While I can still be productive in the afternoons, it requires more effort.

This distinction is even more critical for side hustlers since you have limited time.

If you’re a morning person, for example, you might consider waking up a bit earlier and dedicating an hour to your business before work. Alternatively, you could use your lunch break or work on your side hustle during the night when everyone else is asleep.

To figure out when you have the most energy, pay attention to how you feel throughout the day and note those times when you’re feeling in the zone. It might be in the morning, after lunch, or even late at night.

Everyone’s different, so finding your peak energy is a personal journey.

Once you’ve figured out your high-energy period, schedule your most important tasks during that time.

Whether working on your side hustle, tackling challenging projects, or getting your creative juices flowing, tapping into those peak energy hours will help you get things done faster and better.

Remember, being productive isn’t always about waking up at 5 a.m. and taking cold showers or sticking to a strict routine. It’s all about knowing your energy patterns and working with them.

By honoring your natural rhythm, you’ll be able to get more done in less time.

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Published on November 07, 2023 04:00