Over the past 7 years, I’ve been working my butt off to become fully self-employed.

At the time I started, I was a scared, broke traveler living overseas off the butt of my hard (full-time) work, and I was sick of living that paycheck-to-paycheck lifestyle.

I wanted more for myself.

And I knew that if I was going to get there, I was going to have to start challenging myself to be better than I already was. (Notice how I already was good. You are, too.)

That’s when I started looking into self-help development and finding ways to “level up” (yuck) myself. And while that road eventually ended in burnout, I did manage to find a few challenges that stuck with me afterwards.

So while I’ll never suggest you follow my exact same footsteps (because who in their right mind would suggest burning out?), I do want to share with you those challenges that have stuck with me throughout my burnout healing and neurodivergent self-development.

Let’s get into it.

Summary

This blog post’s a long one, but it’s broken up into many bite-sized pieces for you to chew on without getting overwhelmed.

First, we’ll cover why we even bother with challenges in the first place.

Then, I’ll show you my steps for actually remembering to do the challenges at all, and how you can begin to start challenging yourself today.

Third, I’ll walk you through a handful of challenges I’ve kept up with throughout the years for some inspiration.

And finally, I’ll end you out with some reminders to keep with you while you start.

Sound like a good plan?

Then let’s go!

Why Are Challenges Good In The First Place?

There’s nothing about challenging yourself that makes you better than the next person, but it does give you some major advantages in life.

Mainly, challenges:

• keep your mind sharpened on purpose (not aimlessness)
• break you out of living on autopilot
• help you make the first scary steps (and just start)
• boost confidence and self-esteem

Those all sound like great things, right? Right.

But that doesn’t take away from the fact that you have so much work to do before you even begin a challenge. You have to…

1. figure out what area of your life you want to improve
2. figure out how you could take the smallest step towards that goal
3. and then create a list of rules around the challenge that you’ll follow (however long or short)

It isn’t easy, but that’s the point.

Challenges aren’t supposed to be easy.

They’re supposed to challenge you.

So let’s tackle the first and most obvious hurdle for making challenges happen: Remembering to do them at all.

How Do You Remember To Do Your Challenges?

Want the honest truth?

I don’t remember to do my challenges. Not all of them, at least.

As you’ll see at the end of this blog post, I’ve tried dozens of challenges that never made it past the first week of attempts.

Did that stop me from continuing to try new ones? Hell no.

Here’s what I’ve learned about remembering to do challenges as someone with ADHD:

1. They need to be relevant to a desire I already have.

This needs to be something I ruminate on daily no matter what; something I deeply want to change in my life that I can’t help but remembering.

This makes it easy to build a challenge around, because every time I randomly think of that throughout the day, that’s a chance for me to remember my new challenge.

1. Part of the action plan is a Remember Me plan.

That’s alarms, my calendar, my friends, my family, and building the new challenge into my existing daily routine.

But, of course, I had to build that daily routine initially. It didn’t just magically appear.

So if you’re in that space of building your daily routine, here’s where you start: Small.

How To Start Challenging Yourself

I know you’ve heard this advice before, and I’m going to tell you it again. Hopefully, this time you won’t just brush it off and excuse yourself to “not being able to do that” so that you don’t have to try again.

The advice?

Firstly, start small.

Laughably small. So small it’s impossible for you to start.

For example, let’s say you want to start taking daily walks.

For the first month, you’re not going to take walks. Nope. That’s too big.

Instead, for 30 whole days (or more, if you need it), you’re just going to take a step outside. That’s it. Whether it’s two seconds or two minutes or two hours doesn’t matter. All you’ve gotta do to win your challenge that day is step foot outside.

Are you starting to see how small I mean when I say “start small”?

Secondly, you’re going to need multiple reminders to remember your challenge.

I know I said I build my challenges around a desire I already have, but in the craziness of life, sometimes things get forgotten without us even realizing it.

That’s where building multiple reminders comes into play.

For example, to remember to take my meds, I have a daily calendar notification, two nightly alarms, and a boyfriend that asks me every night if I took my meds. (By the way, before I had a boyfriend, I asked a trusted friend to text me every night.)

Thirdly, make sure your timeline is realistic.

This isn’t going to happen in just a few weeks, friend. It takes an average of 21 days to cement a new habit—and this will likely be longer for your neurodivergent brain.

For example, if you have ADHD, it may never cement, and that’s okay. That’s why we build support systems around remembering and don’t just rely on ourselves.

Finally, give yourself grace, for God’s sake.

You may forget or miss an instance—that’s okay! Don’t stop just because you miss a day or two.

We’re all human. Perfection is never the goal. Just trying, day after day, is.

You don’t have to be perfect to make progress.

You just have to get up tomorrow and try again.

Personal Challenges I’ve Used To Get Ahead In Life

Now that we’ve covered how to start and remember your challenges, let’s get into some of the challenges I’ve used over the past 7 years to get ahead in life, shall we?

1. The 100 Rejections Challenge

The 100 Rejections Challenge was actually stolen from Canadian entrepreneur, Jason Comely, and, for me, it goes like this:

In 1 year’s time, I want to gather up 100 rejections.

Sounds crazy at first, right?

But here’s the thing: This challenge absolutely turned my rejection sensitivity on its’ head.

Instead of being scared of receiving rejections, I was now seeking them out intentionally.

This challenge tapped into my competitiveness and novelty (ADHD brain things!) and helped me see that rejections aren’t as scary once they’re part of your game.

And honestly? Rejections are part of the game of self-employment, dating, socializing, job seeking, posting on social media, and so much more.

Rejections are going to come. So you might as well be ready for them.

2. Take Meds Daily

The first time I was prescribed meds, I thought I’d be over the moon to try them, but… I wasn’t.

In fact, I was so mentally ill and undiagnosed that I couldn’t take my meds daily, and told my doctor as much as that. I just couldn’t do it.

This was the first challenge that took me multiple attempts to get right, but, boy, am I glad I tried again.

Taking my meds nightly has become the basis of my entire self-care routine.

If I don’t take my meds, I don’t wake up the next day feeling do great, and that spirals me into a bad week, etc.

So these days, I have a support system built around taking my meds.

I have a daily calendar reminder, two alarms, and a loving boyfriend who reminds me nightly to take them if I haven’t already.

Now, don’t get me wrong: I still miss days here and there, but it’s nowhere near as bad as the first time around.

3. Journal Daily

Journaling daily has been a dream of mine longer than I wanted to write this blog—and that’s over 15 years in the making.

So I finally turned it into a challenge for myself, by giving myself no minimum amount of words to write per day.

That’s right: I could literally write “I don’t know.” for a journal entry, and it’d still count. As long as I still opened that journal and wrote something, it counts.

Nowadays, journalling is actually built into my workflow to help me clear my head before writing these blog posts or The Daily Divergent.

I still miss days when I’m sick or busy, of course, but that doesn’t mean I count it out.

I just come back the next day and get back on track.

4. No Soda

This is more of a rule than a challenge, but I count it as one anyway.

It’s pretty self-explanatory: As long as I don’t drink a soda, I “win” for that day.

It’s not perfect because I still have juice & Starbucks, but I cut out the sugary bevvies at home at the source—where I’d binge them.

This challenge is important, because it’ll slowly evolve to no snacks, no fast food, no candy, no Red 40, etc, but I just accomplished no soda recently, so I’m moving slowly onto the next one.

One step at a time!

5. Percentage-Based Savings/Investing

I have a very basic rule set-up for saving/investing: For every dollar that comes in, 15% of it is saved or invested (check out Dave Ramsey’s 7 Baby Steps to figure out when you should change from saving to investing).

This rule keeps me consistently saving, even if I end up transferring that money back later on for necessities (but NEVER for wants). The challenge is all about building the muscle, not necessarily about predicting costs (though budgeting is good, too!)

I mention this because we don’t all have the luxury of saving money, and I understand that. I’ve been there many times before.

6. Daily Positive Affirmations

Every day before work, I sit down to journal. And every day before I sit down to journal, I read myself a couple dozen positive affirmations.

I know that sounds like a lot, but that’s because I have a lot of negative self-beliefs.

I use those negative self-beliefs to create my positive affirmations (something I’d love to write about sometime soon, because it’s very powerful work).

Here’s an example of the affirmations I use for blogging:

This has been part of my workflow for as long as I started getting serious about being self-employed full-time—so since about 2020.

And yeah, some days they don’t feel like they’re doing anything, while other days I really need to hear one or two of them.

Overall, building powerful reminders into your daily life is a positive influence on you. And I know you could use more positive influences in your life.

Reminders

• I am not perfect at these. You won’t be, either. That’s unrealistic.
• What keeps them real is that I never stop trying.
• I started small—meds daily was first.
• I have tried dozens of others that didn’t stick: exercising for 3x/week, waking up at 6AM daily, no phone for an hour in the morning, showering 3x/week, saving $X/month, and more. Some challenges just don’t make sense for my lifestyle, and that’s okay.
• The fun is in the process, not the end goal. Challenges should integrate with the person you want to become and the life you want to have, not the person or life you already are/have.

Conclusion

At then end of the day, what worked for me may not work for you, but that doesn’t mean you shouldn’t try.

I hope these challenges have at least offered you some perspective on how small a challenge can truly be. (We don’t have to do 75 Hard to feel accomplished out here.)

No matter where you’re starting, you have a small challenge you can start today.

What part of your life do you want to start improving?

What’s one step you could take towards that right now, today?

Let me know in the comments below, and I’d be happy to share the small challenge I’d set up for myself.