When You Start Questioning the Choices You’ve Made

What if the doubt doesn’t mean you chose the wrong path, but that you’re ready for the next version of it?

Last week, I had lunch with two incredible women.

We had been trying to get together for a while, and when we finally did, we didn't spend much time on surface-level conversation.

We went deep.

All three of us are building businesses. We want to make money. We want to make an impact. We want the work we're doing to matter.

And all three of us were struggling with something.

The specifics are theirs to share, not mine, but as we talked, I realized we were each wrestling with a version of the same question:

Am I still going about this the right way?

Not Should I throw everything away and start over?

Not Have I completely screwed up my life?

Just...

Is the way I've been doing this still the way I want to do it?

We listened to each other. We shared. We laughed. We cried a little.

And because they were willing to be honest about what they were questioning, it became easier for me to be honest about what I had been questioning too.

Turns out, I had a lot to say.

My Inner Dialogue Had Been Going Wild

I've talked a lot about our inner dialogue.

The stories we tell ourselves matter.

I know this.

I coach on this.

And apparently, I needed a refresher course.

Over the past few months, I've been balancing a lot.

I've been hosting my show and handling everything that comes with it. I've been coaching 1:1 clients. I've been doing executive consulting. I've been promoting my book. I launched a new Facebook community. I've kept up with newsletters, blogs and social media. I've been working through my speaker mastery course whenever I can find the time.

And somewhere in all of that, my inner dialogue started getting louder.

Should I pause the show?

Should I stop consulting?

Should I write a children's book?

Do I actually want to speak on bigger stages?

And eventually:

Did I make a mistake going out on my own in the first place?

That one got me.

What started as legitimate questions about my business turned into a full-blown interrogation of nearly every decision I'd made over the past year.

I was spiraling.

One Question Became an Indictment of Everything

When I left my previous career and committed to building SheHandlesIt, I knew there would be risk.

Part of that risk was financial.

I've shared before that building this business required me to take on debt. My husband and I had worked hard to become debt-free, and now we're working hard to pay that debt down so we can rebuild again.

During my little 48-hour funk, I turned that into ammunition against myself.

If I had just worked harder...

If I had stayed longer...

If I had just stuck it out...

We wouldn't have this debt.

Then the story got bigger.

If I hadn't been selfish and decided I needed to start my own thing, maybe we'd have that second house in the mountains by now.

See how quickly that happens?

I went from questioning whether I wanted to pursue bigger speaking stages to blaming myself for our financial position and wondering whether I'd made a mistake leaving in the first place.

One tiny seed of doubt blossomed into a complete meltdown.

And for a minute, I believed the story.

Then I Remembered Why I Left

Staying was an option.

I could have stayed.

But I wanted to leave for a reason.

Actually, for a lot of reasons.

And staying would have kept me exactly where I was without solving any of what I was experiencing.

The truth is, it wasn't my job that was draining me. My job simply didn't offer enough of what fueled me anymore.

I was coming home exhausted and so tense that I felt like a tea kettle ready to blow.

And sometimes I did.

My kids would need my attention at night, and I had nothing left to give. I'd lose control of my emotions and then hate myself for it.

I was going through the motions in survival mode.

On paper, I was building a great life.

But I wasn't really living it.

I was the one holding the duct tape, trying to keep everyone and everything else steady.

Eventually I had to ask myself a hard question:

How well am I serving my family, my company or the people I lead if I no longer feel aligned with the life I'm living?

Leaving wasn't about selfishly choosing myself over everyone else.

In many ways, it was the opposite.

I knew I couldn't be the wife, mom or leader I wanted to be if I stayed exactly where I was.

Leaving gave me back joy.

It gave me back happiness.

It allowed me to experience my life again instead of simply managing it.

None of that stopped being true because a year had passed.

Sometimes You Need to Say the Shit Story Out Loud

Eventually, I talked to Brian.

But I was intentional about how I said it.

I didn't walk into the conversation saying:

I screwed everything up. This is all my fault.

Instead, I said:

“I know this isn't true, but I feel like I put us in this position.”

There's a difference.

I wasn't pretending the feeling didn't exist.

But I also wasn't declaring the feeling a fact.

Then I listened.

Brian let me cry. He let me talk about the guilt I was carrying around putting our family back into debt after we'd worked so hard to get out of it.

And then he looked at me and said:

“That's not how I see it. Look at what we are building.”

Same situation.

Same debt.

Completely different lens.

I was staring at what this year had cost us.

He was reminding me to look at what we were building because of it.

Sometimes the lens we're looking through is skewed.

That's why we need people we trust enough to tell them what's actually going on inside our heads.

Not people who will simply tell us what we want to hear.

People who know us.

People who have watched us.

People who love us enough to say:

“Bitch, you know that shit story you're telling yourself isn't true.”

Sometimes we need reassurance.

Sometimes we need someone to challenge us.

And sometimes we need to hear ourselves say the story out loud so we can finally hear just how false parts of it really are.

I Wasn't Questioning the Decision. I Was Questioning the Timeline.

That realization came during a long walk.

I kept thinking about what was actually bothering me.

And eventually I got underneath it.

I wanted to be further along.

That's it.

I wanted the debt gone already.

I wanted the business making more money already.

I wanted to feel further ahead financially than I did.

And because I wasn't where I thought I should be by now, I started questioning whether I'd made the wrong decision altogether.

Then I reminded myself of something pretty important:

I've been doing this for one year.

One.

365 days.

I was comparing one year of building this version of my life to roughly 25 years spent building the previous one.

How is that a fair comparison?

So I did something I encourage my clients to do all the time.

I treated myself with compassion and grace.

Instead of focusing exclusively on how far I still wanted to go, I looked at how far I'd already come.

And I thought:

If I've done all of this in one year, imagine what I can do in another.

That didn't magically erase the debt.

It didn't suddenly answer every business question.

It didn't mean everything I was doing was right.

Actually, quite the opposite.

Once I stopped beating myself up, I could finally see what really did need to change.

The Spiral Was Wrong About What Needed to Change

This is where I think we sometimes get ourselves into trouble.

We feel uncomfortable and immediately assume the discomfort means we're on the wrong path.

But what if that's not what it's saying?

What if something on the path simply needs adjusting?

At lunch, my friends and I talked about something many entrepreneurs struggle with: how easy it can be to give away the things we do naturally and then struggle with how to charge for them.

As we talked, I started mentally listing the things I tend to offer for free.

Workshops.

Webinars.

Virtual meetups.

Panel moderation.

Emceeing.

Speaking.

Group conversations.

And suddenly I realized:

Those are some of the things I feel most aligned with.

You know what wasn't on the list?

Business consulting.

Don't get me wrong. I love working with business owners. I love helping someone get out of their own way. I love the conversations about leadership, clarity, people and what needs to change.

But walking through financials?

Troubleshooting someone's marketing?

That's work a previous version of me was much more interested in doing.

And maybe I've outgrown parts of it.

That doesn't make taking those clients a mistake.

I needed income while I was building SheHandlesIt. Those clients trusted me, supported my business and helped me get here. I am incredibly grateful for them and for what that work allowed me to build.

But gratitude doesn't require permanence.

Something can have been exactly right for one chapter of your life and still not belong in the next one.

I Can Handle It. But I Don't Want to Handle All of It.

This may be one of the biggest changes in me.

For a long time, I can handle it was practically a personality trait.

Give me more.

I'll figure it out.

I'll carry it.

I'll make it work.

And technically?

I still can.

I could keep consulting.

I could keep coaching.

I could keep hosting the show.

I could keep writing.

I could keep creating content.

I could keep speaking.

I could keep building communities and running workshops and squeezing another thing onto the calendar.

I can handle it.

But if I'm being true to myself?

I don't want to handle all of it.

And that's enough.

Just because I'm capable of doing something doesn't mean it deserves my time, energy and experience.

Some of what I've been carrying was necessary to get me here.

Now I get to be more selective about what comes with me.

Maybe I Don't Want the Stage. Maybe I Want What I Thought the Stage Represented.

There was another uncomfortable realization hiding underneath all of this.

I've spent a lot of time saying I want to speak on bigger stages.

And I do want to speak.

I want to tell my story.

I want to challenge the way people think.

I want to help someone sitting in an audience question whether they're actually living the life they want.

And yes, I want to be paid for the experience and value I bring.

But somewhere along the way, I think I started confusing the stage with the impact.

They're not the same thing.

The hardest thing for me to admit was that I may actually create more of the impact I want in a smaller room.

I saw that at the retreat.

I see it when I facilitate workshops.

I see it in deep conversations.

I see what happens when people don't just listen to me, but interact with me and with one another.

At first, questioning the big-stage goal scared me.

Am I afraid?

Is this imposter syndrome?

Am I creating an excuse so that if I fail, I can say I never really wanted it anyway?

Those were fair questions.

But after sitting with them, I realized I wasn't trying to shrink the dream.

I was getting clearer about what the dream actually is.

I want to make an impact.

I want depth.

I want real conversations.

I want to create spaces where people leave thinking differently than when they walked in.

Sometimes that may happen on a big stage.

Sometimes it may happen with ten women sitting in a circle.

Both count.

Playing Small Doesn't Always Look Small

This realization also forced me to admit something else.

I had been playing small in places I didn't recognize.

Not because I wasn't doing enough.

God knows that wasn't the problem.

I had been playing small by giving away some of the work I feel most aligned with because I hadn't fully understood the value I brought to it.

After the retreat, I know differently.

I know I can create impact through group coaching.

I know I can help multiple people at the same time.

I know people don't have to show up to a free Zoom for me to create meaningful conversations and transformation.

I'd been focused heavily on getting 1:1 clients.

So guess what I kept getting?

1:1 clients.

Now I'm working on changing that.

I'm removing traditional consulting as an offering and building out group coaching while adding more depth to the way I present my 1:1 work.

This isn't about figuring out how to make people pay me more money.

It's about building a business that makes money from the work I actually want to commit my time, energy and experience to.

There's a difference.

And I think every time we level up, we're asked to admit where we've still been playing small.

Sometimes playing small looks like being afraid to try.

Other times it looks like continuing to do everything you're capable of doing because choosing what you actually want feels scarier.

Questioning Yourself Doesn't Always Mean You're Lost

Here's what those 48 hours taught me.

Not every moment of doubt means you're on the wrong path.

Sometimes doubt is asking you to take another look at the path and decide what still belongs on it.

Maybe you're questioning a career you once desperately wanted.

A business you worked hard to build.

A relationship.

A goal.

A version of success you spent years chasing.

Before you decide the original choice was wrong, get curious about what you're actually feeling.

Maybe the decision was right then.

Maybe you've changed since you made it.

Maybe the destination still feels right but the way you're trying to get there doesn't.

Maybe you're not regretting your decision at all.

Maybe you're frustrated with your timeline.

Maybe you've simply reached the point where the version of you who got you here can't be the only one deciding what happens next.

Coaching Reflection: Tell the Story Out Loud

If you're in your own funk right now, don't immediately make a life-changing decision from inside it.

But don't ignore it either.

Get quiet.

Then pay attention to how you're talking to yourself.

There's a big difference between:

“I made a terrible mistake.”

and:

“I know this may not be true, but right now I'm afraid I made a mistake.”

One is a verdict.

The other creates room for exploration.

Then tell the story to someone you trust.

Someone who loves you enough to care about your feelings but respects you enough not to simply agree with everything you say.

And then actually listen to them.

Ask yourself:

What part of this is fact, and what part is fear?

Am I questioning the decision or the timeline?

Does the goal no longer fit, or does the way I'm pursuing it no longer fit?

What did this choice give me that can't be measured on a spreadsheet?

What once served me that I may have outgrown?

If “I can handle it” isn't the standard anymore, what do I actually want?

You may discover that you really do want to change direction.

That's okay.

You may discover you're exactly where you're supposed to be.

That's okay too.

Or, like me, you may realize you don't need to start over.

You just need to realign.

The Next Level May Require a Different Version of You

A year ago, I knew why I needed to leave.

That why was real.

The fact that I questioned myself a year later doesn't erase it.

I didn't make the wrong choice.

And I don't need to keep making every choice that helped me survive the first year of building something new simply because those choices worked then.

I'm clearer now.

Clearer about the work I want to do.

Clearer about how I want to make money.

Clearer about the kind of impact I want to make.

Clearer about what I want more of.

And maybe even more importantly, clearer about what I don't want anymore.

It took about 48 hours of self-doubt, imposter syndrome and some old wounds rearing their ugly heads to get me there.

Apparently, they needed one more opportunity to remind me who was in charge.

And eventually I had to look at them and say:

No. Again, sis. I'm in control.

Not because I have everything figured out.

But because this time, I'm willing to listen to the questions without letting fear write the answers.