My Business is at a Crossroads (And To Be Totally Honest, I’m OK With It)

My business, JL&Co, is at a crossroads.

The truth is, it has been at a crossroads for quite some time.

Since starting JL&Co nearly four years ago, things have been good. Really good!

We’ve figured out our core services, our client roster continues to grow, and excitingly, each year JL&Co earns more than the year before.

And that’s just the business side of things — more importantly, I love the life that JL&Co allows me.. I appreciate the flexibility in my schedule and the opportunity to choose the companies and people I want to work with.

But every once in awhile, I get asked a difficult question that I’m not quite sure how to answer:

What’s next for JL&Co? Do you think you’ll grow even bigger?

I never quite know how to respond to this question, and that’s because at this point, I see two clear paths JL&Co could take — and I’m truly not sure which path I’ll choose.

The crossroads I’m currently facing

JL&Co could take two distinctly different paths — perhaps even more than two, though these are the two most obvious I’ve identified thus far.

Both paths are lovely, challenging and rewarding. Both appeal to me in different ways.

Let’s take a closer look.

Path #1

JL&Co continues to grow and thrive.

We get BIG! We continue to bring on more and more clients. Naturally then, the team expands. Maybe we have 10 employees — maybe one day we have 100 employees!

Perhaps the company stays remote, or one day we have office space. My dream of seeing JL&Co on an office wall comes to fruition.

This feels like the natural path for an agency — a well-worn path many folks I admire have trekked before me. And to be honest, this feels like the most “traditional” path for a business like mine to take. (But since when do I do traditional, let’s be honest.)

Let’s explore the pros and cons.


  • Obviously, JL&Co becomes more profitable. That’s always a priority.
  • JL&Co has the opportunity to make an even bigger impact on the businesses we work with. We get to work with more awesome companies and brands!
  • I get the chance to make a personal difference in the lives of other communications professionals whom I could potentially employ. How cool would that be?!


  • In this scenario, I drift away from the actual work that I love, and step into the role of CEO. Overseeing a full team would take me away from writing, editing and pitching and take me into the role of a manager.
  • Business likely gets a lot more complicated — financially, legally, logistically. If I thought starting a business was difficult, I’m sure things get even tougher once you add full-on employees and office space into the mix.
  • I lose some flexibility and freedom in my schedule.

Path #2

JL&Co continues to grow, but stays relatively small and niche.

We bring on new clients strategically, knowing that at our current size we’ll likely have a cap as to how much work we can bring on, instead becoming more selective about who we work with.

In this scenario, I continue to work with clients/my small team, while running this blog and pursuing other side hustles and passion projects. I continue to work from wherever I want, whenever I want.

This is my current path, and it’s one I’ve come to love.

Time to take a look at the pros and cons here:


  • I get to continue to do the work I love! I stay in the nitty-gritty of the day-to-day work, getting face time with my clients and team.
  • I keep the flexibility in my schedule that I’ve grown to appreciate. (I know for certain this will come in handy when it comes time to start a family.)
  • I have the room and brain space to explore my creativity and passion projects.


  • Perhaps years down the line I feel less challenged continuing to do the same type of work. Maybe I get sick of the nitty-gritty of working with clients and want to step into a bigger leadership role.
  • JL&Co may not thrive as much as it could if I were to choose a different path. It might stay the same, never making an impact beyond what we’re currently doing.
  • JL&Co likely won’t be as profitable as in path #1.

Fighting growth or staying smart?

Awhile back, my significant other Tim said something that stopped me in my tracks.

That analogy hit me hard — it came at a time a year or so back when I was struggling to decide if I should bring on a big client because I wasn’t sure if me and my small team could handle the volume of work.

I started to wonder, “Am I fighting growth?”

I began to ask myself if I was fighting growth because of fear — or because of something else.

In the case of that one particular client scenario, I was fighting growth out of fear, but in the case of my current crossroads, I think it might be something else.

In this case, I think I’m being smart — smart in taking my time to make this decision, smart in protecting the flexibility I wished for on the days I sat at my desk from 8-5.

I’m at a crossroads — and I’m OK with it

So as you can see, I remain at a crossroads.

I can make all the pros and cons lists in the world. I can debate this decision with myself day and night.

But honestly, this is a crossroads I’m totally OK with sticking at for awhile longer, whether that means one year or 10 more years.

I can always choose to grow JL&Co bigger, but once it becomes bigger, I don’t see myself being able to reel it back with success.

So for now, I’ll accept this crossroads for what it is, choosing to feel gratitude that I even find myself here in this place of opportunity and choice.

And when the time comes? Perhaps the choice will be clearer, but for now, I’ll continue to go with the flow, evaluate each new opportunity as it comes and continue to embrace the wonderful life my current path has given me.

Fellow business owners, can you relate? And for everyone, tell me about a time you were at a crossroads. I’d love to hear how you handled it in the comments below.


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Meet Jessica

I live by the saying “Life begins at the end of your comfort zone” and help others do the same to reach their biggest, brightest goals. Read my story here.

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