The Art Of Letting Go: How Savvy Business Leaders Grow By Delegating

Delegation is more than a skill, it’s an art. It requires self-awareness, trust, and a willingness to evolve. But for many leaders, it’s also the key to unlocking new levels of creativity, impact, and growth.

We asked entrepreneurs from the Dreamers & Doers community to share the most challenging things they had to let go of in their businesses and how they finally did it. You’ll learn about the fears they faced, the systems that helped, and the mindset shifts that made all the difference.

Let these stories serve as your reminder: You don’t have to do it all, or do it all alone, to be successful.

Founder & CEO of Forward Collective Group, a global management consulting firm partnering with entrepreneurs and business leaders to build companies people love to work for and buy from. 

I was afraid of sacrificing quality for the sake of efficiency. I’d had a ton of false starts with new hires and felt it was easier to do everything on my own. I was wrong!

I realized that my area for growth was creating a better selection process and onboarding experience to ensure new hire success. The result was phenomenal social media management to start the year, which got me tons of leads, new clients, and social impressions to drive my 2025 business goals.

CEO & Founder of Ask a Chief of Staff, a boutique executive search and career development platform focused on placing and empowering strategic operators—primarily Chiefs of Staff—into roles that accelerate leadership teams and scale startups.

The hardest part to let go of was being the default person for every decision. As a founder, it’s easy to feel that no one can care as much as you do, and I clung to operational control far too long. Letting go felt like losing touch with the heartbeat of the business, but in reality, I was holding back growth.

Building a team I deeply trust and shifting from “how do I do this?” to “who is best equipped to own this?” changed everything. Letting go doesn’t mean you’re less involved; it means you’re focused on the highest-leverage things only you can do.

CEO of Dora L. Rankin Consulting LLC, providing high level support for women who want to live their purpose and create wealth by customizing coaching for women in all stages of business, from high level corporate women starting consulting companies to venture backed startups. 

The first and hardest thing to let go of was knowing I couldn’t and didn’t have to do everything. I had to be very introspective and truly inventory my role, focusing on activities that generated revenue and outsourcing the rest. Today, I am the CEO, and I delegate all aspects of the company except for vision, growth, and strategy!

CEO & Founder of The Hive, the team behind your growth—empowering entrepreneurs, elevating businesses.

My company helps other founders delegate, and recently, I had to put that into practice myself. As we aimed to grow, I had to step back from being directly involved in client accounts. I couldn’t keep being the final touchpoint for everything! The hardest part is knowing that—no matter how ready you are and how many systems, documents, and processes are in place—something will inevitably slip through the cracks. Watching that happen is tough, but what matters most is staying focused on the bigger vision and making thoughtful adjustments as you move forward.

Founder & CEO of BAUCE Magazine, a lifestyle site for self-made women creating and curating content, resources, and tools that help black female entrepreneurs build million-dollar enterprises.

The hardest part of my business to let go of was the content creation, especially the writing—I absolutely loved that part! But I hit a wall eventually! Trying to create all the content alone was burning me out fast. I got serious about delegating after attending a women’s conference where a panelist said, “You can go faster with a team than doing it alone.” This powerful statement completely transformed my perspective and has remained with me, helping me focus on the abundant opportunities that come with building a larger team and empowering me to delegate more systematically. 

Remember that good delegation isn’t about giving up control; it’s about creating space for your unique genius to shine while empowering others to grow alongside you. 

Chief Swag Officer & Co-Founder of Go To Market, the anti-boring branded merch and swag experts changing the way the world handles swag and designing sustainable branded merchandise shops that reflect our clients’ brand values. 

For many tasks and jobs in my business, it was not only easy for me to delegate but a relief to do so because it freed me up to do the things I love. Still, I held on to financial tracking with a white-knuckled grip until recently—five years into running my business! It was hard for me to let go because I was holding onto the idea that your financials are supposed to be a secret, even from people who can help you grow. I finally realized that, if I want to grow as a leader, I need to let go of all the administrative tasks that were bogging me down—not just the ones that are easy to delegate.

Founder & CEO of Em Dash Content Studio, a boutique team of expert writers and strategists that help businesses show up on search and establish themselves as thought leaders.

It was hard for me to let go of client communication. As we grew, it became harder to manage client communication on a day-to-day basis, and I had to delegate this task to operations. I was open and transparent about the shift, making sure to have introductory meetings with my Director of Operations and each client. I also assured clients that I would still be involved and that they could come to me with questions or concerns at any time. 

Founder of Jasz Rae Digital, a HubSpot consultancy that helps sales and marketing teams turn their tech investment into real revenue through smart strategy, streamlined systems, and clean data.

Letting go of the backend implementation and data cleanup was tough because I used to do it all myself, and I’m meticulous about the details. But I realized that spending my time there was keeping me from the strategic work that lights me up and delivers the most value for my clients.

What helped most was realizing that delegation doesn’t mean stepping back. It means leveling up. I began building a team of specialists who care just as deeply as I do, and now I get to lead the vision while trusting others to execute with excellence.

Founder of BeeKyn, a playdate matching and scheduling platform that helps caregivers connect with new families based on shared interests, kids’ ages, and availability—and effortlessly coordinate with friends they already know. 

The hardest thing to let go of was perfection. It sets an impossible bar and delays putting something valuable into the world. Embracing progress over polish meant accepting that growth comes from feedback and that imperfect action is how real momentum builds.

This was my mindset shift: letting go doesn’t mean losing control. It means trusting your vision enough to let others help bring it to life.

CEO & Founder of Spark the Fire Grant Writing Classes, an internationally recognized professional development company that guides leaders to improve their grant writing skills to fund causes that make the world a better place.

My passion is teaching people to write grants, but I realized I can’t grow the company and grade all the grant proposals. I hate to admit it, but working ten-hour days, seven days a week is what it took to realize something had to give.

Hiring teaching assistants was a feat of trust and letting go, but I’m so glad I did it. Every time a student comments about how helpful their TA is, I know I made the right decision. Now, I wish I had done it a long time ago!

Founder & CEO of Better Together Agency, transforming communications by integrating AI tools to optimize operations, develop campaigns, and address systemic biases in generative AI. 

Relinquishing control of operational and new business tasks was my greatest challenge because I worried that delegating might mean losing touch with day-to-day insights that fuel our purpose-driven work. I feared that stepping back from these frontline activities would disconnect me from the pulse of our agency and the nuanced understanding that drives our advocacy-centered communications.

Adopting Notion—which provides visibility without micromanagement—as our project management platform, transformed my approach to delegation. It created a perfect balance between maintaining strategic oversight and empowering my team to own their responsibilities and bring fresh perspectives to our work.

Founder & CEO of 100 Degrees Consulting, providing CFO and bookkeeping services to nonprofits around the globe.

The hardest part for me to let go was client work. I started my business because I genuinely loved the work, but I eventually hit the ceiling of my time, energy, and capacity. I knew that in order to grow the business and make a bigger impact, I couldn’t be the one doing all the work anymore.

Letting go was hard because I worried clients wanted me, specifically. The mindset shift came when I realized that delegating wasn’t about stepping back from quality—it was about building a team that could uphold and even enhance it. Once I hired the right people, developed a strong training plan, and built systems to standardize our work, it became much easier to let go. I saw that I could still ensure excellence without doing everything myself, and that trust in my team was the key to truly sustainable growth.

Founder & CEO of Ninety Five Media, a woman owned and operated digital marketing agency specializing in creating high converting content that’s 3x’s our clients’ growth. 

The hardest part of my business to let go of was client communication. As a young founder, I took pride in building relationships and being the direct point of contact, but I quickly realized it wasn’t scalable. Letting go felt scary at first, but I knew empowering my team to manage those touch points would ultimately serve our clients better than I could on my own.

I let go of the idea that I was the only one who could do it “right” and started trusting the systems we built and the team we hired to execute them. ClickUp became a game-changer for creating visibility and accountability across our workflows. Pairing that with a strong onboarding process helped me feel confident that nothing would fall through the cracks. This shift has made delegation less about giving something up and more about creating space to lead.

Founder of Searchlight Digital, an all-women search marketing agency that specializes in taking the scary out of SEO through done-for-you marketing support that boosts online visibility and increases conversions.

For a long time,I believed that as the face of the company, I also had to be the only point of contact for my clients.

What changed my mindset was putting my clients’ experience and results ahead of my own ego. If someone else on my team was able to reply faster and provide better service than I could, it was my responsibility to keep my client’s needs at the forefront of my decisions. We solved so many miscommunications, dropped balls, and bottlenecks by making the switch that I wish I did it sooner!

Having systems, automations, and training in place to help empower my team to succeed has allowed me to make sure that my high standards are embedded into everything we do—without having to do it all myself!

Founder & Managing Principal of Kōvly Studio, the brand and marketing agency for experience-driven brands.

I joke that my business was my firstborn child, so giving up true ownership of responsibility to anyone else was extremely difficult. But bringing on the right team has hands down been the most helpful shift. I’m so grateful for my team and the dedication and commitment they bring every day, which allows me to feel completely comfortable with them taking the lead in different areas.

Founder & CEO of Sage Haus, helping busy parents reclaim time by building their village, recruiting house managers and family assistants to lighten the mental load and support families in implementing home systems that streamline household management and improve partner collaboration.

The hardest part of my business to let go of was writing every single caption on social media. I wanted the voice to feel so authentically me, like you were hearing from a real mom in the thick of it instead of a brand. But once it started feeling more draining than energizing and I found a social media manager I could trust, letting go felt like a weight lifted. I finally had space to focus on what only I can do.

Even as someone who teaches delegation for a living, the real shift came when I stopped expecting people to do things my way and started trusting them to figure it out their way. Delegation isn’t just about handing off tasks—it’s about handing over ownership.

All individuals featured in this article are members of Dreamers & Doers, an award-winning community that amplifies extraordinary women entrepreneurs, investors, and leaders by securing PR, forging authentic connections, and curating high-impact resources. Learn more about Dreamers & Doers and get involved here.