Managing a single business is already a handful, but overseeing several? That’s a whole different ball game. Speaking from experience — having owned over 30 businesses — as CEO, adding new ventures has become almost second nature. Over time, I’ve gathered numerous strategies (and some rather amusing anecdotes) that make juggling multiple businesses not only feasible but truly rewarding. Here’s my playbook on what has been most effective for me.

1. Time management is your superpower

Time is the most precious resource for any entrepreneur. For someone overseeing multiple companies, it’s critical to master time management. I allocate specific time blocks to each business or priority task — for example, during my early days of running two companies, I reserved mornings for one and afternoons and evenings for the other. This method reduced distractions and kept my focus sharp on what’s most important each day.

I’m a strong proponent of the 80/20 rule: concentrate on the 20% of activities that deliver 80% of the results, and don’t hesitate to delegate or eliminate the rest. Technology plays a crucial role — my digital calendar (and handwritten one) help keep both me and my businesses operating smoothly and efficiently.

Capitalize on every spare instance. I tend to review emails, proposals, or agreements while cooking or eating. This simple tactic ensures I remain productive and avoid squandering time on tasks I can tackle quickly during downtime. Every minute is valuable!

2. Delegate like a pro

No one can do it all — nor should they try to. I’ve learned, sometimes the hard way, that identifying what to delegate and to whom is essential. I focus on my strengths, such as brainstorming and strategic planning, while leaving specialized tasks to experts.

Assembling teams of skilled, reliable individuals is a must. If employing full-time staff isn’t feasible, skilled freelancers and virtual assistants are readily available with just a few clicks. One of my real estate marketing businesses involves significant content creation and marketing for luxury properties in California. Outsourcing tasks like graphic design or video editing allows me to concentrate on growth strategies.

3. Prioritize ruthlessly

Trying to juggle everything will only make you dizzy. That’s why prioritization remains one of my top skills. Every business I run gets its own set of goals, usually mapped out each quarter, and these guide my daily and weekly priorities. Not everything is urgent; knowing how to identify genuine emergencies versus issues that can wait is burnout prevention 101. And if a similar task pops up across several businesses — like a round of contract reviews or a big content-planning session — I tackle them together to maximize efficiency.

4. Get (and stay) organized

Organization is the thread holding this circus act together! For each venture, keeping communication, files and workflows in order — saving hours that would’ve otherwise been wasted hunting for that one lost document — is crucial. Documenting processes is also clutch; clear operations manuals empower my teams and simplify onboarding when it’s time to grow. Additionally, every Friday, I dedicate 30 minutes to decluttering my desk, cleaning out my inbox and closing open loops in my schedule. This process has saved my sanity more than once.

5. Protect your work-life balance

Let’s be real: with multiple businesses, the temptation to work nonstop is strong, but burnout isn’t an option. I set firm boundaries. Although I love to work 24/7, I still take time to relax — usually, when my body says I have to. And I still make sure to pencil in downtime regularly, from daily exercise to mealtime and fun events.

I also try to work in business industries that I genuinely love. When I invest in hobby-based ventures, it never really feels like work. Let’s say you are a baseball card collector and you turned it into a business venture — you could attend card-collecting events and visit hobby shops as part of your workday. Blending passion with business keeps things exciting and fulfilling. These recharge moments fuel the energy and creativity I need for the week ahead. And, when those wins — big or small — come rolling in, I always take a breath to celebrate the progress. It’s a great morale boost that reminds me why I love the hustle.

6. Stay flexible and keep learning

If I’ve learned anything across my 30+ businesses, it’s that adaptability is a must. Every venture throws new curveballs and every mistake is another lesson in disguise. Sometimes, I would take on too much or get hung up on tasks I should have let go, but every stumble made me a better business owner. Keeping up with market trends, being open to pivots and investing in self-development — whether by attending conferences, coaching platforms, diving into leadership books or connecting with other entrepreneurs — makes me more effective and keeps my companies ahead of the curve.

7. Enjoy the ride

Juggling multiple businesses can feel like a high-wire act (and sometimes, it is), but with planning, the right team and an openness to learning, it’s absolutely possible — and incredibly rewarding. No entrepreneur starts as a master juggler. Skills build over time, and the satisfaction that comes from watching your business thrive is second to none. So, trust the process, enjoy your wins and go show the world just how much you can accomplish!

Whether you’re just starting or already deep into the entrepreneurial juggle, I hope these tips can help you make the most of your amazing adventure.