The Embarrassing Reality Of Working For Myself

Is building an online business or YouTube channel worth it?

After a decade of self-employment, I’m opening up about the challenges, the freedom, and the real strategies that helped me earn a living on my own terms.

From weekly meetings with myself to finding the right mentors, I’m sharing what works and what I wish I’d known sooner.

Okay, I have to be honest with you about something.

Sometimes I wonder if I’m doing the right thing by encouraging people to start an online business or grow a YouTube channel.

There. I said it!

I know that sounds a little wild coming from someone who literally teaches video strategy for a living.

But stick with me, because this is not the highlight-reel version of entrepreneurship.

This is the weird, awkward, bumpy, and genuinely embarrassing reality of what it actually takes to earn a living from your own online business.

And I’m feeling extra reflective right now because this week marks 10 years since the last day I was ever employed by someone else.

So yes, we are absolutely celebrating!

But we’re also getting really honest.

Because if you’re building an online business, or even just thinking about it, you deserve the full picture, not just the pretty parts.

Now, I’m pulling back the curtain on a decade of self-employment and sharing the things I wish someone had told me a whole lot sooner.

It’s one of my most personal episodes yet, and I think you’re really going to love it!

VIDEO: The Embarrassing Reality Of Working For Myself

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How I Became Self-Employed

I didn't start my business because I had everything figured out.

My business and YouTube channel started while I was working a full-time job. My kids were super little, and my husband had a wacky shift schedule; somewhere in the middle of all that, I started feeling like I wanted to become a content creator.

At first, I wanted to be a blogger.

Then I thought, maybe I should make YouTube videos too.

That instinct turned out to be a really good one.

About a year and three months into that little side hustle, my position at my full-time job was eliminated.

The company restructured, relocated, and eliminated my position.

Suddenly, the decision about whether I should eventually leave my job wasn't entirely mine anymore.

Throughout the next 10 years, I've asked myself the same question more times than I can count:

Should I just go get another job?

I've asked myself that at least once a year.

It's not because I don't love what I do.

It's not because the business isn't working.

Being self-employed is simply hard in ways that are difficult to understand until you're actually living it.

There isn't always a clear path.

Nobody is necessarily standing over your shoulder telling you what needs to happen next.

You have to create that structure for yourself.

The Hardest Part of Being Self-Employed? Managing Yourself

One of the biggest things I wish I had figured out sooner was self-accountability.

When you're employed, someone else usually provides some kind of structure.

A boss, manager, or supervisor might say, “Here's what we need from you this week.”

You have deadlines, meetings, responsibilities, and people expecting you to complete certain things.

When you're self-employed, that external accountability can disappear.

At first, that feels like freedom.

You can do whatever you want!

That freedom can become a problem, though, when you don't have a structure that tells you what actually needs to happen.

There are definitely days when I open my computer and go down whatever rabbit hole I feel like.

In fact, on the morning I recorded this episode, I woke up and watched the final episode of Outlander before doing any work.

I stayed in bed with my coffee and watched the series finale because I wanted to avoid social media spoilers.

And honestly?

That was fine.

The problem isn't taking a morning off.

The problem is when taking the morning off turns into taking the week off, and then the month starts getting away from you.

Being self-employed requires enough structure to give you freedom without letting that freedom derail the business.

That's something I've gotten much better at over the years.

My Monday Meeting With Myself

Every Monday morning, I have a meeting with myself.

Yes, really!

I've borrowed some principles from Gino Wickman's Entrepreneurial Operating System, or EOS, and adapted them to make sense for a business my size.

My business is essentially me plus two people who work remotely from other countries.

I don't have a giant leadership team.

Instead, I've taken the pieces that make sense for me and built my own weekly agenda.

Here's what that looks like.

1. Start With Personal Good News

The first thing I do is write down at least one thing I'm grateful for.

Usually, it's something that happened over the weekend with my family.

That tiny step helps me start the week by noticing something that's already going well before I jump into business mode.

2. Look for Good News in the Business

Next, I write down something that's working inside the business.

Maybe someone inside Video Brand Academy has shared a win.

Perhaps a podcast episode was recently published.

Sometimes it's simply something that happened in the business that I'm genuinely excited about.

Taking a moment to notice those things keeps me connected to the progress that's already happening instead of immediately focusing on the next problem.

3. Review the Calendar

Then I look at my calendar.

Of course, the appointments are already there.

Still, if I don't consciously review them at the beginning of the week, they can sneak up on me.

I might suddenly realize I need to leave the house for an appointment even though it has been sitting on my calendar for three weeks.

Writing those commitments down at the beginning of the week helps them stick in my brain.

4. Choose Three Things to Complete

This is one of the most important parts of my weekly agenda.

I choose three things I want to complete that week.

Not three things I want to work on.

Three things I want to finish.

There's always more than three things that need to happen in a business. That's just reality.

Most weeks, I don't complete all three.

Something else comes up. A priority changes. An unexpected project becomes more important.

That's okay.

The goal isn't to predict the future perfectly.

The goal is to start the week with a clear idea of what matters most.

5. Keep Track of Bigger Projects

I also have a list of bigger projects for the year.

I think of these as “rocks,” borrowing another concept from EOS.

They're essentially projects I want to implement, complete, or integrate into the business.

Those priorities can change throughout the year, but having the list gives me a bigger-picture view of where I'm going.

It keeps me from looking only at whatever happens to be directly in front of me today.

6. Track a Few Important Metrics

Finally, I track a few basic metrics.

New leads.

Sales.

Videos published.

Things like that.

I'm not spending hours analyzing the numbers every Monday.

Instead, I'm simply recording the information so I can see what's happening over time.

Then I move on.

Why I Don't Use Time Blocking

You might notice something missing from my system.

Time blocking.

I'm not a big fan of it for myself.

When every hour of my day has a specific boundary, I immediately see those boundaries as rules I'm about to break.

And because I'm the person who created the rules, I'm also the person who can break them.

Instead, I prefer to look at my week as a whole.

I know where I have meetings and appointments.

I know the three things I'm trying to complete.

Then I have some flexibility within the week to figure out when the actual work happens.

That gives me structure without making me feel completely constrained.

For me, that's a much better balance between freedom and accountability.

Keep Your Priorities Where You Can See Them

Creating a weekly agenda isn't enough if I put it away and forget about it.

My weekly agenda stays in front of me throughout the week.

When I used a paper notebook and bullet journal style, this was easy.

Now that everything is digital, I've had to get a little more creative.

I have a small vertical monitor positioned below my camera, and I use it as my accountability monitor.

My weekly agenda is right there.

I can see what I said I wanted to accomplish.

I can see my priorities.

Most importantly, I can remind myself what I'm supposed to be doing instead of letting whatever happens to be interesting at that moment take over.

It's almost impossible to ignore.

Almost.

How I Use AI to Stay Accountable to Myself

I've also started leaning more heavily into AI as part of this system.

My weekly agenda lives in Obsidian, and I've connected my Obsidian setup to Claude Code.

I also have it connected to ClickUp and my email.

When I sit down and think, “What am I supposed to be working on right now?” I can literally ask Claude.

It can look at what I've said I need to do, what's in ClickUp, what's overdue, and what I've already committed to.

Then I can decide what I'm actually going to work on.

Here's the interesting part.

I'm not really accountable to the AI.

The AI is simply something I created to help me create accountability for myself.

Once I tell it, “Okay, this is what I'm going to work on,” I have this little mental connection that makes me want to finish it so I can go back and say, “I got it done.”

That small feedback loop helps me stay on track.

Sometimes I Need to Zoom Way Out

Another thing I’ve learned about myself is that I sometimes need to see the entire business, not just a task, project, or the next item on my to-do list. To make that possible, I’ve created mind maps, used sticky notes on the wall, and tried different ways of visually mapping how everything fits together.

I've tried different ways of visually seeing how everything fits together.

Right now, I use ClickUp for project management, and I have several operations lists organized around different areas of the business.

There's growth, which includes things like content, launches, promotions, offers, and lead magnets.

There's fulfillment, which covers delivering on the offers and what's happening inside Video Brand Academy.

Then there's admin, which includes things like paying team members and doing taxes.

I have a ClickUp dashboard where I can see those areas together.

It isn't necessarily the best way to manage every individual project.

That's not why I use it.

I need to see the whole thing.

When I can see the business on one page, my brain can go, “Oh yeah. This is what we're doing.”

Without that bigger picture, I can feel like I'm floating around inside a business that I created without knowing exactly where I'm going next.

The “Now What?” Stage of Being Self-Employed

That's actually where I am right now.

I've built the business to this point.

And now I'm asking:

Now what?

I have a hundred different ducks, and none of them feel like they’re in a row.

So naturally, my first instinct is to add another duck: start this, try that, build this thing, or add another project.

The problem is that I can have the best intentions in the world while still focusing on what I feel like doing instead of what the business actually needs.

That's the shift I'm beginning to make.

Instead of constantly asking:

What does Meredith want to do today?

I'm starting to ask:

What does the business need to have happen?

That separation between myself and the business is new territory for me.

For a long time, the business was simply an extension of me.

Now I'm starting to think about what the business itself needs in order to keep growing, keep building momentum, and keep moving forward.

It's a different way of thinking.

I'm still figuring it out.

Being Self-Employed Doesn't Mean Doing It Alone

One of the things that has contributed to my personal and business growth over the last 10 years is having other business owners around me.

People who understand what it is like to build this kind of business, who I can bounce ideas off, who can coach me, and who I can support in return.

People who get the weird, awkward, bumpy parts of entrepreneurship because they are experiencing them too.

That kind of camaraderie makes being self-employed feel a lot less lonely.

I've also stayed connected to a larger business community through my mentor, James Wedmore.

One thing I've appreciated about Business By Design is having a more comprehensive framework for the business side of my business.

There are so many people teaching different strategies.

One person teaches webinars.

Another teaches YouTube.

Someone else teaches lead magnets.

Another person teaches a completely different way to generate traffic.

You can end up creating what I think of as the Frankenstein effect.

You take one strategy from here, another from there, and another from someone else. Eventually, you're trying to make a bunch of pieces work together even though they weren't necessarily designed to fit together.

I've certainly learned from many different people over the years.

Having a more cohesive system for the business side gave me a path to follow when I didn't know what I was doing.

The YouTube and audience-growth side is my area.

The business-building side is where that framework and mentorship have been particularly valuable for me.

Would my business have been successful without it?

I'm sure I would have figured things out somehow.

But I don't know if I would have enjoyed the process as much.

And that matters.

Would I Choose Being Self-Employed Again?

After 10 years, would I do it all over again?

Absolutely.

There are probably hundreds of things I would do differently if I knew then what I know now.

That’s just part of the journey.

We figure things out, live and learn, adapt, change, improve, and tweak along the way.

Then we do it all again.

The biggest reason I would choose being self-employed again is actually pretty simple.

I would always wonder if I could do it.

Could I start a business from nothing, grow it enough to earn a living, and make this unconventional online business actually work?

Now I know the answer: yes, I did it.

I can check that off the bucket list.

The next question is what happens beyond simply earning a living.

That's the transition I'm in now.

I'm figuring out what the next level looks like, what the business needs from me now, and who I am as the person running it.

I don't have all of those answers yet.

And I think that's okay.

Conclusion

Ten years of being self-employed has taught me that entrepreneurship isn’t a straight line.

Some seasons are exciting. Others are stressful. Some weeks you feel incredibly productive, and other weeks you find yourself watching television in bed before you have done a single thing on your to-do list.

Sometimes you feel completely clear about where the business is going. Other times, you wonder what you’re even supposed to do next.

That doesn’t necessarily mean something is wrong. It means you’re running a business.

For me, the key has been building enough structure to create stability without taking away the freedom that made me want to be self-employed in the first place.

My Monday meeting with myself gives me direction, my weekly agenda keeps me accountable, and my visual business map helps me see the bigger picture.AI tools help me stay on track. Community and mentorship help me feel less alone and give me people to learn from.

Those structures don’t eliminate the weirdness. They make the weirdness manageable.

After 10 years, I can honestly say that I would choose this path again.

Even with the awkward parts, the uncertainty, and all those ducks that still refuse to get in a row!

Because I would always wonder what might have happened if I hadn’t tried.

So here’s to 10 years of being fully self-employed. And, as I joked at the end of the episode, fully and basically unemployable at this point. 🥂

If you’re building your own business right now, you don’t have to have everything figured out.

Build the structure that helps you stay accountable. Find people who understand what you’re doing. Give yourself enough freedom to enjoy the business, but enough structure to keep moving it forward.

Then keep going!

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