👋 Hi my name is Roslyn, I’m a 2x founder and executive coach. I help founders fall in love with building their companies again. Learn about working 1:1 here.

Hi there,

One of my biggest (and ongoing) challenges as a founder is letting go of control. Historically, control has felt safer for me (and my nervous system). And yet, I’m coming to understand that trying to control things keeps me from a more intelligent and easeful flow of life.

Today I’m talking about letting go of control in the context of your team. As leaders we need to learn to delegate and trust, so that our company can grow bigger than just us.

Today we’ll cover:

• The deep down reasons we struggle to let go of control

• What thoughtful delegation can unlock for us (and how holding tightly stifles growth)

• The inner and outer work of letting go of control and empowering our team

But first…

I’m hosting a free masterclass for purpose-led entrepreneurs on October 9th on how to finish the year with intention, focus and flow. Sign up here.

And if you’re in NYC this Friday, I’m hosting a female founder coffee walk, to create meaningful conversation and community amongst some incredible founders in the city. RSVP here.

Where we go deep on the outer work or the inner work of building a startup.

How to Let Go

So your business is growing. You’ve hired a team around you to help fuel that growth. 

But instead of feeling lighter, you notice you’re still holding on tightly. Maybe you’re struggling to fully delegate, or you’re delegating but can’t resist hovering, worried the work won’t meet your standards unless you’re directly involved.

Deep down, you know this isn’t sustainable. It keeps you stuck in overwork, robs you of time for the high-impact work only you can do, and prevents your team from taking ownership and growing into leaders themselves.

And yet… letting go of control feels harder than it should.

This is something I see over and over with my clients, and it’s something I lived through as a founder myself. My guess is you’ve felt it too at some point, right?

Today, I want to unpack why this happens, the costs of clinging too tightly, and what you can do to delegate with more trust and ease, from a practical, emotional and spiritual lense.

“WHY AM I LIKE THIS?!”

If you’ve ever asked yourself that while struggling to let go of control, you’re not alone. Founders often bump up against the same patterns when it comes to delegation. 

Below are a few of the most common ones I see with clients (and have experienced myself). 

As you read through them, just notice (without judgment!) if any of these feel familiar.

1. PERFECTIONISM (FEAR OF IMPERFECTION AS A THREAT)

For some of us, the drive for “perfect” execution runs deep. Handing work off feels dangerous because if it’s not done flawlessly it could mean failure: of a task, a project, the whole business, or even of ourselves as leaders. Underneath that is usually fear. 

If things aren’t perfect:

• The business will die and I’ll be unsafe.

• I’ll be judged as [inadequate, a bad leader, not good enough, etc.]

• I’ll be rejected by my business partners / investors / team

2. PEOPLE PLEASING: PROTECTING OTHERS FROM DISCOMFORT

We may resist delegating because we assume our team won’t like the work, especially if it’s’ something we personally find boring/frustrating. In reality, that’s often just projection. I used to do this with admin tasks I didn’t enjoy, and guess what? They weren’t a good use of my time, and they left me burnt out.

At the root of this belief: If I make someone do something they don’t enjoy, they won’t like me and I’ll lose their approval/loyalty. Or they’ll quit.

3. FEAR OF BURDENING OTHERS

On a similar note, some of us may have also internalized the belief early on that “my needs are a burden.” Delegating can unconsciously feel like putting pressure on others, making them carry something heavy. Instead of asking for help or assigning work, we over-function, doing more than is sustainable, while quietly resenting that no one is helping.

4. IDENTITY & SELF WORTH TIED TO DOING

Many of us built our companies by initially doing everything ourselves, so we sense our value is wrapped up in execution. Delegating threatens that identity. 

If I’m not the one doing, am I still needed? Am I working hard enough? Will people respect me?

Subconsciously we’re equating “not doing the task” with “not being valuable”

5. NERVOUS SYSTEM PATTERNING: CONTROL AS SAFETY

On a subconscious level, our nervous system may equate control with survival. If we grew up in an environment where things felt unpredictable, taking charge became the way to feel safe. Delegating then isn’t just a work decision, it triggers old wiring that says:

If I’m not in control, bad things will happen.

6. LACK OF TRUST & CLARITY IN TEAM

Delegation can also feel scary if our team isn’t fully proven or expectations aren’t clearly defined. In early-stage startups, processes and standards can sometimes still be unclear so delegating can feel like setting things up to fail.

THE DOWNSIDES OF NOT DELEGATING

Okay so because of one, or many (or all) of the reasons above, you’re not delegating as much as you could be. Why is this a problem?

While it’s not your fault, if you want your company to continue to grow and flourish, it is your responsibility to figure out how to disrupt these patterns. 

Otherwise you’ll be faced with the following issues:

• Your team isn’t empowered to grow. Without opportunities to stretch, they may become disengaged or even leave.

• You can’t focus on your highest-impact work. Time spent in the weeds keeps you from strategy, growth, management or however you contribute best.

• You burn out. Carrying everything yourself leads to exhaustion, resentment, and health risks.

• Execution slows down. If everything funnels through you, progress slows and opportunities get missed.

• Culture suffers. Lack of trust leads to micromanagement, stifling creativity and ownership.

THE UPSIDES OF DELEGATING

On the flip side, what do you stand to gain if you can figure out how to gently release that control?

• Your team develops faster. Delegation builds skills, confidence, and leadership in others. They might make mistakes, but then they learn from them and grow.

• You free up energy for higher impact. Letting go gives you space to focus where you add the most value.

• Momentum increases. With more people moving projects forward, things get done faster.

• You protect your wellbeing. Sharing the load sustains your energy, clarity, and creativity.

• Culture strengthens. Trust and ownership cultivate innovation, collaboration and loyalty.

• External confidence grows. Investors and customers see a scalable company, not a founder bottleneck.

Okay so all of this sounds good right? So… how can we actually let go of control?

HOW TO LET GO AND DELEGATE

I’ll make suggestions from both the outer and inner work perspectives.

THE OUTER WORK: BUILDING STRUCTURES & TRUST

Delegation feels more possible when you know your team can succeed without you. 

Here are a few ideas for how to do this:

• Play to your team’s strengths: Map your team’s zones of genius and notice where they enjoy tasks you don’t. They actually want you to delegate these opportunities to them!

• Delegate outcomes, not tasks: Share the “why” and “what good looks like,” then let them figure out the “how.” This empowers them and gives them the opportunity to learn and grow.

• Coach for growth: Show how their work connects to the company strategy and their personal development plan. This empowers and energizes them and helps them feel more ownership and leadership around their responsibilities.

• Hire for ownership: Choose people who naturally take initiative, and let go of those who don’t.

• Create space: Step back (even have days where you’re unreachable) so others can build confidence and solve problems without you. (Taking that vacation fully off allows you to see what your team can do without you. It’s probably a lot more than you think).

• Support, don’t micromanage: Weekly or biweekly progress and support check-ins keep things aligned without micromanaging.

• Normalize mistakes: Frame errors as part of the learning process and encourage open communication + retrospectives.

• Systematize: Document processes, create decision-making filters (e.g. for hiring, spending, prioritizing), and record Looms so knowledge isn’t dependent on you.

THE INNER WORK

While the above list can help us feel more comfortable trusting our team, if our resistance sits at the subconscious or nervous system level, then the inner work will be just as necessary to success here.

Here’s how we can work with what’s happening on a deeper level.

1. WORST CASE SCENARIO JOURNALING

This exercise helps us pull our fearful thoughts out of the subconscious level and into the light where we can understand it and work with it. 

i) What’s the absolute worst thing that could happen if I let go of control? List all the what if’s. 

For example, if I let my employee own this partnership without my supervision, they might mess it up or misrepresent our company. We could lose the partnership, which might hurt growth and reputation, making it harder to raise our next round. And then the company might die and I’d be seen as a failed leader without income or credibility. 

ii) If the worst-case scenario were to come true, how would it threaten your identity, self-worth, sense of belonging or safety? 

For example, it would challenge my identity as a capable, valuable leader and threaten my financial security and chance at financial freedom.

iii) If the worst-case scenario came true, are there any alternative positive beliefs you could take away instead?

If we lost the partnership, maybe it wasn’t aligned anyway. If fundraising failed, perhaps it’s a sign to focus on profitability.

iv) If it came true, what are the positive aspects in your life that could support you through it? (Loved ones, coaches, investors & community, referrals from great customers/clients,  alone time in nature, other income portals, other skills you could utilize, etc.). 

For example, my skills, network, loved ones, and ability to generate income in other ways (consulting, new ventures) would still be there.

*This journaling exercise is from To Be Magnetic.

2. PARTS WORK

This exercise helps us understand what your “protector parts” (e.g. perfectionist, people-pleaser, etc.) are trying to protect you from.

i) Identify the part of you that’s trying to control things in order to protect you.  

For example, maybe a people-pleasing part keeps you from delegating a task because it wants to keep your employee happy.

ii) What’s its job? How does it do its job? 

Maybe it’s job is to rationalize to keep you from delegating: “It’s just 30 minutes a day.” Or “If I delegate, they might hate their job and quit.” Or “It’ll take too long to train them.”

iii) What is it trying to protect you from experiencing? From feeling? 

Maybe it’s shielding you from feeling disliked, rejected, or inadequate as a leader.

iv) Show loving appreciation for this part’s good intentions. Love it and accept it exactly as it is.

Say to this part “I can see how hard you’re working to keep me from feeling rejected, judged and inadequate. I really appreciate your efforts and positive intention”. (Even if you don’t agree with how they’re doing it, it’s important that this part feels valued exactly as it is, without you trying to change it or convince it to act otherwise).

v) Allow yourself to experience the feeling it’s trying to protect you from feeling. Show yourself compassion. 

Reconnect with the feeling of being rejected and judged in your body. Put a hand over the body part you feel it in. Breathe deeply into that space. This is likely a younger hurt part that remembers how it feels to be rejected, judged, unlovable, not good enough. Show that part the loving compassion they deserve (and didn’t receive at the time). You can say something like “I really get how hard it is to feel rejected in this way. I’m here with you. I accept and love you exactly as you are”.

3. NERVOUS SYSTEM REGULATION

Often, our urge to control comes from not feeling safe. This can show up as a fight, flight, freeze, or fawn response. 

In a moment where you notice yourself wanting to hold tightly, micromanaging or resisting delegating, try this:

1. Notice how you feel in your body. 

• How is my posture (open, relaxed, vs. tense, collapsed)?

• How is my breathing? (deep, slow versus shallow, rapid)

• What sensations do I feel in my body?

• What’s happening in my emotions? (fear, anxiety, frustration, scared, dissociated) and where do I experience those emotions in my body?

2. Take a moment to step away from your laptop and move your body.

Consider how you feel in your body and how it might feel good to move.

• If you’re anxious, restless or worried (flight response) shaking out your body from head to toe, going for a walk, or slowly walking around your space and orienting to it might feel good.

• If you’re angry or frustrated (fight response), punching a pillow, vigorous shaking, strong exhalations or primal sounds can feel good.

• If you feel numb or dissociated (freeze response), gentle movements (wiggling fingers & toes, rolling shoulders), pressing your feet onto the floor, a body scan, rocking or swaying or light stretching can feel good.

• If you’re noticing yourself people-pleasing or over-accomodating (fawn response) you could try pushing your palms away from you or taking a power stance (wide stance, hands on hips, stand tall, chest open).

These practices can help you complete your body’s survival response in small, titrated ways, instead of staying stuck in it.

3. Reconnect with your values and inner wisdom.

Once you’re feeling more safe and relaxed in your body, from this place, think about what action feels most in alignment with your goals and values. Consider what action feels light, open, or good in your body.

Is there a way to test this action out in a small, manageable step?

4. TRUST & SURRENDER

As a founder who has traditionally loved to try to control outcomes (FYI, not possible lol!), one of my biggest (and ongoing) lessons has been learning to surrender and trust that the universe might have a better plan for me than anything I could engineer myself.

Can you relate? 

If so, here are a few practices that have been helpful:

i) Reframe challenges

When setbacks arise, see them as opportunities for growth (instead of seeing yourself as a victim of external circumstances). 

• Ask: “How am I being given the opportunity to let go of old patterns?”. “How do I want to respond to this?” 

ii) Build trust in the universe

Observe and build your awareness of when things work out better than you could’ve planned.

• Notice the moments where you hear your intuition and try following it. Notice when things work out better than you originally imagined. (You can start small here and build trust up to bigger decisions and situations).

iii) Leaning into spiritual practices

Like meditation, prayer, journaling, or gratitude practice. 

• I’ve recently been meditating on this song: “I Release Control”.

• Check out last week’s newsletter on daily practices for more inspiration.

iv) Consuming spiritual content

I find consuming spiritual content on a daily basis really shifts my mindset to trust and openness to the flow of life.

A few books that have spiritually expanded me include:

• The Surrender Experiment by Michael Singer 

• A Return to Love by Marianne Williamson

• Outrageous Openness by Tosha Silver 

• And my friend Becca’s brand new memoir It’s Gonna Get Messy (so great and relatable - it comes out in a week!)

I hope you’ll follow your intuition on which of the above actions and exercises feel good for you, and give them a try!

FEMALE FOUNDER WALK

I’m excited to be hosting the first of a series of Female Founder Walks this Friday, September 26th, starting in the West Village.

My goal with these walks is create space where purpose-led founders can learn from one another, connect deeply and feel supported through the demanding, soul-expanding journey of building a business.

Each walk will have a discussion theme and this one is around blocks. We’ll be chatting about:

• As we move into Q4, how do you want to move forward in your business? What would feel like meaningful progress or alignment for you?

• ​What blocks do you feel are keeping you from moving in that direction?

• ​How does this block tend to show up day-to-day, in your energy, focus, or the way you lead?

• ​If this block were trying to protect you from something, what might that be?

• ​If you imagine this block lifted, what becomes possible for you and your team?

Deep & meaningful chats + coffee + movement outside sound fun?

You can find out more about the event and RSVP here.

Q4 RESET: END THE YEAR WITH INTENTION, FOCUS & FLOW

I’m hosting a ​60-minute masterclass for purpose-led entrepreneurs on October 9th.

​As we head into Q4, maybe you’re feeling the pressure to finish strong, the chaos of competing priorities and that creeping sense that you’re running out of time…

​This masterclass is your chance to pause, reset, and end the year on your terms: with clarity, alignment, and focus. It’s for founders who want to grow sustainably, without burning out, and create the kind of business (and life) that actually feels good.

​I’ll walk you through a 4-part framework for closing out the year with clarity, confidence, and capacity:

• ​Reconnect with your why

• Refocus on what matters most

• Align your team & time

• Strengthen the foundation (aka you and your capacity)

The founders who finish strong don’t try to do everything — they get clear, focused, and aligned.

​This is your chance to end 2025 with intention and ease, so you can step into the new year with momentum, clarity, and confidence.

RSVP here.

• 1:1 Coaching: Head into Q4 feeling focused and in flow. Book a free coaching consultation to learn how we’ll work together on this.

• Group Coaching: Click here to stay in the know on when our next Within Group Coaching cohort launches.

• Let’s be friends: on LinkedIn and Instagram. I share more startup content and what’s going on behind the scenes there.

• Finally, tell me how you liked this newsletter. I read every piece of feedback.

Appreciate you!

With love,
Roslyn 💚