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After finding success in one business, entrepreneurs will often dip their toes in one or more other businesses, either as the founder, a board member or in another leadership capacity. While this can be very rewarding to do, it can also be the cause of a lot of stress if not managed properly. Overlapping schedules, a bursting to-do list and not nearly enough time for everything that needs to get done can quickly turn a rewarding endeavor into an overwhelming one.
So how do serial entrepreneurs do it? According to the business leaders of Rolling Stone Culture Council, the secret lies in the following 12 tips. Here, they expand on each one, offering up their best advice for any aspiring entrepreneur on how to juggle multiple businesses and responsibilities at the same time.
Focus on What Will Have the Biggest Impact
Out of all the tasks you’re juggling, what responsibility will make the most impact on the world? Bring your focus there. Stay disciplined on what serves the earth and our communities. That would be my advice. – Philip Wolf, Cultivating Spirits
Get Your Timing Right
It’s all about timing. Odds are that your daily agenda will commonly have overlapping obligations. It’s best to lean into that, starting with a list of the most urgent priorities. Create a calendar that ensures that your more formidable roles and tasks coincide with less taxing duties or less pressing engagements while also ensuring tasks are realistically within your daily, weekly or monthly capacity. – Magen Baker, Bell + Ivy
Build Highly Competent Teams
For serial entrepreneurs, the key to managing multiple businesses effectively is to build highly competent teams. By doing so, you can stay high-level and meet the demands of each venture, empowering your teams through trust and strategic direction. This approach ensures businesses thrive under strong leadership, freeing you up to explore new opportunities with confidence. – Shirin Etessam, OML
Ensure You’re Bringing Real Value
Before committing to a new enterprise, you must consider the value you can bring to it. Growing a portfolio of businesses can be highly rewarding and even future-proof your success. However, it’s crucial to avoid having it become a false economy that consumes too much of your revenue-generating operations’ time. – Michael Klein, cannabisMD
Get Total Alignment From Your Team
Team, process and automation are everything for running multiple businesses. Trust people who can have conversations and make decisions on your behalf, clear waypoints where you are directly involved and invest in tools to replicate processes. Most of all, ensure everyone is clearly aligned with your vision so you can work on the businesses and not in them. – Tim Jack, Rise
The Rolling Stone Culture Council is an invitation-only community for Influencers, Innovators and Creatives. Do I qualify?
Have a Strategic Plan and Stick to It
Juggling a number of businesses as an entrepreneur can be tricky, but the key to success in boosting your bottom lines is having the right professionals in place to help scale your ventures and set realistic goals for growth. Strategic planning is important; in other words, don’t take on too much at once and don’t try to do everything yourself. Have a plan and stick to it with devoted teams. – Paul Fitzgerald, Salt & Pepper Media Inc.
Approach Work as Play
It’s critical to keep the brain stimulated, especially as an entrepreneur. You can’t forget to leave space for play. The key to success with a side gig or new endeavor is just that: Approach it as play. Take calculated risks, but let them be driven by passion, not by the rules you have to live by in your “normal” work life. And as always, surround yourself with people who want to do cool stuff. – Sarah Jenkins, The Romans New York
Keep Your Business Ventures Related
Diversification is important, but don’t over-diversify. When you dip your toes into another business, make sure it’s related in some way to your primary business or industry. For example, I run a cannabis PR firm, sit on the boards of multiple cannabis advocacy organizations and am involved with multiple dispensaries and smoke shops. I avoid getting distracted by totally unrelated undertakings. – Evan Nison, NisonCo
Define Clear Roles and Delegate
Entrepreneurs must delegate effectively, fostering capable teams for each venture. Clear communication and defined roles empower teams for smooth operations. Prioritize time management, leverage technology, and adapt regularly to balance diverse business demands. – Sonia Singh, Center of Inner Transformations
Bring on a Partner Who Can Help You
An important part of continued success is learning to balance responsibilities. What often seems to make the most sense is bringing someone on board who has an understanding and who can help run the day-to-day operations. This allows you more time to focus on the overall needs, branding and strategy of the business and continue growth based on what the goals at hand are. – Chris Bianchi, CB Entertainment
Learn From One Business and Apply It to the Next
We can find knowledge almost anywhere. Take what you learn in one business and apply it to the next one because many of the principles are very similar. Even if you need to pivot slightly, you can almost always learn lessons in one field and make yourself more valuable in another. Don’t be afraid to think outside the box and find similarities where others might miss them. – Julie McQueen, CarbonTV
Take Better Advantage of Your Time
Focus on time management. This means letting go of certain things — perhaps doing a video call versus a lunch, or taking a train versus driving so you can work. Plan meetings and errands geographically near each other. Delegate to someone you trust and/or want to give more responsibility to. To save even more time, stop micromanaging. – Susan Johnston, New Media Film Festival®
