Five Years in Business: Lessons on Growth and Motherhood

Five years ago, I left teaching.

I did not have a perfectly mapped-out five-year plan. I was not thinking about building a team, hosting a podcast, creating a community for moms in business, or becoming known for Dubsado.

I mostly knew one thing: I could not keep doing what I was doing.

Leaving teaching was not an easy or impulsive decision. I had spent years preparing for that career, and I lost sleep for months worrying about whether I was making a huge mistake.

But I also knew I needed something different.

Looking back now, I never could have predicted where that one decision would lead me.

That is probably why I had such a hard time recording this podcast episode. I originally planned to share five lessons from five years in business, but every time I tried to record it, the episode felt forced.

The last five years did not happen in five neat lessons.

They happened through pivots, random opportunities, becoming a mom, meeting the right people, changing my mind, asking for help, trying things that did not work, and slowly becoming more confident in what I am building.

So instead of forcing my story into a list, I sat down at our actual kitchen island with the person who has watched all of it happen: my husband, Nick.

And we went back to the beginning.

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I Did Not Leave Teaching Because I Had Everything Figured Out

When I left teaching, I was terrified.

I had gone from college straight into a structured school schedule. Someone else told me where to be, what needed to get done, and when my workday started and ended.

Then suddenly, I was home.

I had one client.

And I was supposedly a business owner.

I remember sitting on the couch thinking, “Okay…what do I do all day?”

There was so much freedom that it almost felt uncomfortable. I could get coffee at 10:30 on a Tuesday. I could work outside. I could set my own schedule. But without the structure I had followed for my entire adult life, I had no idea what my days were supposed to look like.

I started as a virtual assistant because it gave me somewhere to begin.

I never thought virtual assisting would be the final version of my business. I didn’t know what that final version was yet.

I built my first website without knowing what I was doing. I sat on the couch and taught myself Dubsado. Nick and I set up my first office, then moved it what felt like twelve times over the next five years.

It was awkward, uncertain, and far from polished.

But it got me moving.

That is something we do not talk about enough in business. You do not need to know exactly what your work will look like five years from now before you can begin.

Your first offer does not have to be your forever offer. Your first version just needs to give you a place to start.

My Business Changed Because My Life Changed

Virtual assisting eventually evolved into blogging and Pinterest. I built websites, learned Dubsado, experimented with different services, and added retainer clients.

Then my life changed too.

I became pregnant with Madelyn.

The decision to become a business owner had always been connected to the kind of life I wanted someday. Even while I was teaching, I remember wondering how I would balance that career with being the kind of mom I wanted to be.

Entrepreneurship felt like it could give me another option.

What I did not realize was how much becoming a mom would change what I needed from my business.

My time was more limited. My capacity had changed. And work that once made sense no longer fit the life I was building.

Before having a baby, I could look at a service and think, “This makes money, so I will keep doing it.”

After having a baby, the question became, “Does the amount of time and energy this requires actually make sense?”

At the time, I had several blogging retainers. That recurring income felt safe, but producing every blog and managing Pinterest required a lot of hours each month.

The work was profitable. It just was not supporting the life I wanted anymore.

That was one of the first times I understood that a successful offer is not only one that makes money. It also needs to make sense for your time, your energy, and the season of life you are in.

Becoming a Mom Did Not Magically Create Work-Life Balance

I wish I could tell you I perfectly prepared my business for maternity leave, stepped away for three months, came back refreshed, and everything ran beautifully without me.

That is not what happened.

I was still early in business. I did not have a company that could operate for months without me.

I had clients. I needed income. And I was trying to figure out how to work while also learning how to care for a newborn.

There were days when I called Nick because Madelyn would not sleep, I had work that needed to get done, and I genuinely did not know what I was supposed to do.

We made plans like, “You will come home at three, then I will work.”

Those plans lasted approximately two days.

We tried babysitters. We changed schedules. We figured out naps. We found childcare. When something stopped working, we adjusted again.

That has been one of the biggest lessons of motherhood and business. There is no perfect schedule, childcare arrangement, or right way to build a business as a mom.

You figure out what works for your family, and you adjust when it stops working.

That flexibility has mattered through every season since. It mattered while we were raising a toddler. It mattered while we moved, renovated a house, and spent months answering questions about plumbing and childcare between client calls.

Owning a business did not make those seasons easy. But it gave us more options for making them work.

Then I Walked Into a Room That Changed Everything

One of the biggest turning points in my business happened when I booked a ticket to an in-person conference.

There was not a major strategy behind it. I simply decided to go.

Then I walked into a room filled with women who were moms and incredibly successful entrepreneurs.

I felt completely out of my league.

These women understood their brands. They understood marketing. They walked into brand shoots knowing exactly which photos they needed, which props to bring, and how they were going to use every image.

Meanwhile, I was basically thinking, “Oh, we are taking pictures? I guess I will wear something nice.”

I had no idea what I was doing.

But being in that room completely changed what I thought was possible.

I met women building businesses in photography, branding, coaching, calligraphy, and so many other industries. They were ambitious. They were successful. They were also moms.

They were not choosing between motherhood and building something meaningful. They were figuring out how to make room for both.

And I remember thinking, “Wait. You can do this?”

That conference gave me more than business advice. It expanded what I believed was possible for my own life.

Getting Off the Internet Changed My Business

For a long time, I thought growing a business meant sitting behind my computer and posting on Instagram.

The internet played a huge role in helping me build this business. But getting into rooms with other people changed it in a completely different way.

I met people who became clients.

I met people who became close friends.

I met mentors who helped me see my business more clearly.

During a hot-seat coaching session at that conference, I talked about the blogging and Pinterest retainers I was still holding onto. They brought in reliable income, so letting them go felt terrifying.

But as I talked through what I wanted next, the answer became obvious.

I could not keep building the next version of my business while holding onto every piece of the old one.

Sometimes growth means adding something new.

Sometimes it means finally letting go of what no longer fits.

I Stopped Trying to Build Everything Alone

Another big change was learning to ask for help.

When I started as a virtual assistant, the idea that I might one day hire a virtual assistant of my own felt almost impossible.

Then I hired a few hours of support and realized how much could change when I stopped trying to carry every task myself.

I have worked with wonderful assistants over the years, including Virtual Bliss and now Rock Solid Virtual Assistants. Billie has become my right-hand woman for marketing, and I have also added support with client work.

Delegating did not come naturally. I had to learn how to explain my process, trust someone else with work that mattered to me, and let go of the belief that taking care of my clients meant doing every single thing myself.

But building a team gave me room to start this podcast, meet more people, support my local community, and think about what I want the business to become next.

Support costs money. It also gives me back something I can never create more of: TIME.

My team helps me serve more clients without lowering the level of care I want every person to receive. It also creates more time for my family, my ideas, and the work that truly needs me.

The Part I Wish I Understood in Year One

I think about this all the time.

When I started my Instagram account, I had zero followers.

Literally zero.

Nobody knew what I was doing. I barely knew what I was doing.

Now I can look around and see clients, friendships, a team, a podcast, a community, and opportunities that would not exist if I had not made that first decision to leave teaching.

But none of it happened overnight.

If you are in year one watching someone in year five, you are looking at five years of decisions you did not see.

Five years of awkward first attempts.

Five years of changing offers.

Five years of investing before it felt comfortable.

Five years of meeting people.

Five years of figuring out what I am good at.

Five years of becoming the person who can run this version of the business.

We all want to skip that part.

We want the confidence now. We want the clients now. We want the audience now. We want the clear offer now.

But sometimes it really does take time.

Five Years Later, I Am Still Not Done

The funny thing about reaching five years is that I do not feel like I have arrived.

I feel like I am standing at the beginning of another chapter.

Dubsado is still a major part of my business. I care deeply about every client who trusts me with the behind-the-scenes pieces of their work. I want them to leave with a business that feels easier to run, a client experience they feel proud of, and more time for the people and priorities outside of work.

But I am also thinking bigger about systems, client experience, strategy, mentorship, and community.

Made for Mothers has introduced me to women who are asking many of the same questions I am.

How do we build successful businesses and still have lives?

How do we grow without constantly being online?

How do we get real time back?

How do we become more ambitious without building businesses that consume us?

I do not know exactly what the next five years will look like.

Five years ago, I could not have pictured this version either.

You Do Not Need to See the Whole Path

If I could go back to the version of me sitting on the couch with one client, building a website and wondering what she was doing, I do not think I would give her a perfect business plan.

I would tell her to keep going.

Take the opportunity.

Change the offer.

Walk into the room even when you feel underqualified.

Ask for help.

Let go of the thing that is no longer working.

Build the childcare.

Build the systems.

Meet the people.

And give yourself more time than you think you should need.

Your first version does not have to be your forever version.

You do not need to know what year five will look like from year one.

You just have to be willing to start.

Listen to the full podcast episode to hear Nick and me talk about the decisions, detours, and people that shaped my first five years in business.

And if you are ready to build systems and a client experience that better support where your business is headed, explore all the ways you can work with me here.

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Podcast Show Notes: kellymccracken.co/podcast