How To Know When It’s Time to Hire an Assistant (Before You’re Drowning in Work)

There’s a moment — an unmistakable, gut-wrenching moment — when you realize you can’t keep doing it all. Maybe it’s when you forget to send a final payment reminder to a client and now their dream vacation is in jeopardy. Maybe it’s when you realize you haven’t taken a day off in months, and your family is starting to wonder if they need to book an appointment just to have dinner with you. For me, that moment came on a gold couch in my living room, in the middle of a conversation with my husband that I’ll never forget.

I was drowning.

Not in the slow, gradual way where you can feel the water rising. No, this was the kind of drowning where one second you're treading water, and the next, you realize you're completely underwater, gasping for air. I had built a thriving business, but it had become unsustainable. Every email, every client request, every administrative task was on my plate. And I was exhausted.

Sitting there on that couch, my husband looked at me and said, “This isn’t working. Something has to change.” And he was right.

I had spent so much time trying to be everything to my business that I hadn’t stopped to ask myself if I was running it — or if it was running me. That conversation was my wake-up call. And if you’re reading this, I hope this is yours.

Don’t Wait Until You’re Drowning

The biggest mistake I see travel agents and agency owners make is waiting too long to hire an assistant. They tell themselves, I just need to push through this busy season, or Once I hit a certain revenue number, then I’ll bring someone on. But by the time they finally admit they need help, they’re already overwhelmed, making it even harder to find the right person, train them and set up the systems that will make them successful.

The truth? You want to hire before you reach the breaking point. You want to bring in support while you still have the capacity to properly train and integrate them into your business. Because an assistant isn’t just someone who “takes tasks off your plate.” A great assistant becomes an extension of you — handling client communication, managing details and ensuring nothing falls through the cracks.

But here’s the kicker: hiring an assistant without solid systems in place is like handing someone a map with no destination.

Systems + Assistants = Freedom

When I first hired an assistant, I wish I had known how critical it was to have solid systems in place. I thought, I’ll just hand over tasks as they come up. Big mistake.

Without documented processes, my assistant was constantly waiting on me for direction, and I found myself micromanaging instead of actually getting relief. It wasn’t until I implemented systems — clear workflows, automation for repetitive tasks and structured onboarding — that I finally felt the impact of having an assistant.

And that’s when everything changed.

Now, when a new inquiry comes in, my CRM (Customer Relationship Management system) automatically assigns a follow-up task. When a client’s final payment is due, the system sends a reminder. My assistant knows exactly when and how to jump in because the process is already built.

This combination of automation + delegation is what gives you real freedom. You get to step away from the day-to-day chaos and focus on what actually grows your business — whether that’s booking high-end clients, designing group trips or simply reclaiming your evenings with your family.

An Assistant Is an Investment, Not an Expense

I know what you’re thinking: But hiring an assistant costs money!

Yes. Yes, it does. And so does burnout.

Burnout costs you in missed opportunities because you don’t have the bandwidth to take on new clients. It costs you in mistakes because you’re juggling too much. It costs you in personal time — those moments with your family and friends that you can never get back.

An assistant isn’t just another business expense. They are an investment in your sanity, your business growth and your ability to serve your clients at the highest level. The right assistant allows you to operate in your zone of genius — doing what you do best while they handle the rest.

What I Wish I Knew When I First Started

If I could go back and talk to myself on that gold couch, here’s what I would say:

• Hire before you think you need to. If you’re already feeling overwhelmed, you’ve waited too long.
• Set up systems alongside your assistant. A great assistant paired with automation will change your business and your life.
• Stop seeing help as a luxury. It’s a necessity if you want to scale without sacrificing your sanity.

And most importantly?

You don’t have to do it all alone.

If you’re at that moment — if you feel the weight of your business pressing down on you, wondering how much longer you can keep juggling everything — take this as your sign. The right assistant, with the right systems, can change everything. And the sooner you make that move, the sooner you get back to doing what you love.

And maybe, just maybe, you’ll get to sit on your own gold couch, breathe a little easier and finally feel in control again.