KEEP ON DREAMING UP
For the ambitious "I CAN’T DO JUST ONE THING" people who constantly have all the ideas and crave multiple businesses, projects, and income streams to feel whole.
I help you build a sustainable ecosystem and an aligned rich life.
KEEP ON DREAMING UP
KEEP ON DREAMING UP
My mission is simple: to help the "I CAN’T DO ONE THING" people build a sustainable ecosystem between their ideas, income, lifestyle and execution. To reduce the scatter and burnout and make the “scattered” become your superpower. I know this because I am one of you.
You have multiple businesses, projects, or big ideas but they feel scattered and don't speak to each other
You feel unclear and overwhelmed but your ambition keeps you creating anyway
You are in a deficit all the time.
You're unclear about your impact, mission, or what your unique magic actually is and how to channel it all into something sustainable or an aligned rich life
Ideas are constantly roaming but not landing, or you struggle to execute and sustain effectively
You have habits that aren't working and they're keeping you from great leadership and growth
Life and work feel fragmented—not functioning as a successful ecosystem
You're dealing with fear of change, doubt and scarcity mindset.
There's a pull in your heart that you don't know how to answer
You're missing pleasure, presence, and being seen in your “I can’t do one thing” mind.
Don’t feel seen in other programs and offers.
Does This Sound Like You?
We've been offered a script on life that doesn't match what's in our hearts.
When ambitious people who can't do just one thing try to force themselves into linear paths and it's exhausting. But when your multiple businesses, your creative projects, your work, and your life are aligned and functioning as one ecosystem—there's ease, clarity, and rich living that feels good. When the ideas come, we don't shut off, we can’t so the energy becomes diffuse creating overwhelm and frustration. We keep moving towards some semblance of success. So building an aligned ecosystem really matters.
“Sheri has been central to my personal growth, emphasizing the interconnected balance in all aspects of life. Her guidance and programs helped me better understand the motivators behind relationships—both romantic and professional; through her guidance I was able to foster deeper romantic relationships and be more focused in my founding journey at the same time, leading to a more fulfilling, balanced life".
Andrei I. - Startup Founder + Consultant
I work with ambitious entrepreneurs, leaders, and high-achievers who feel wired to create multiple opportunities and income streams.
You might already be running a business and wanting to start something new, have exited or left a job and ready for the next impactful step, balancing a corporate career with side passions, or wanting to build something entirely new. You've tried really hard to juggle all the pulls you have and even niche down, but it doesn’t feel authentic at all. Your mind actually rallies against you (no matter how much you meditate and intention set). Plus, it’s doesn’t match the pull of life.
LUCKILY, THIS IS YOUR TIME AND THE WAVE OF THE FUTURE.
Where I Meet You
I work with ambitious entrepreneurs, leaders, and high-performers who can't do just one thing. You might be running multiple ventures, juggling a corporate career with creative outlets, the office generalist or building something new while maintaining what you've already created. Whatever the case, you're ready to build and grow in a way that feels aligned.
Multiple Efforts, No Cohesion
You have business, projects, or income streams not to mention life responsibilities and wellbeing needs, but everything feels scattered and draining.
Diversifying & Expanding
Building additional revenue streams, growing deeper in your current business, or adding new ventures that align with your ecosystem
Wellbeing & Lifestyle Goals
You want your success to support the life you actually want—pleasure, presence, relationships, and feeling good and I provide the aligned tools specific to you where you are.
What Stays, What Goes
Clarity on what's draining your energy versus what deserves your focus
Savvy Systems
It’s important to have the right systems, knowing when to outsource/hire, tech tools and foundation to sustain all the ventures and creative efforts.
You're wired for doing multiple things. The world tells you to "niche down" and "focus on one thing," but that's felt right for you. I help you design an ecosystem where all your varied interests, businesses, and creative outlets work together—so you can thrive doing what you love, sustainably.
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"Working with Sheri has been truly transformative for me. When I started working with her, I didn't even know the questions I had about myself. I just knew I wasn't happy, and thought perhaps someone with her talents and deep empathy could help shake things up for me. Well we shook things to the core together for sure! I've been going through a lot of my life not understanding my worth, and my purpose. I think to an extent I performed as a comedian in most social situations, the way many codependent people do. That's now drastically changed since working with Sheri. Suddenly I can ASK for things. I can listen and not feel the need to perform. That that happened in my 40's is something I will never be able to repay her for. As a result, I feel and understand my value now. I walk more confidently into any conversation. I understand that I may not be for everyone, but that doesn't matter. Provided I stick to my mission and my values, I'm exactly where and who I'm supposed to be. And that feels amazing. Thank you Sheri."
– Raphael W. - Entrepreneur
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It has always been a good experience working with Sheri Chiprout. She is a source of reliability and integrity that I have experienced throughout the many years I have known and worked with her.
John C.
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“I want to thank you from the bottom of my heart for supporting me so fully during the biggest transition of my life! After ending my marriage, selling my house, quitting my job, and moving across the country with no plan at all - you really helped me to ground and set up new roots in order to grow the life of my dreams! You encouraged me to fully tap into and trust my Self while establishing some much needed discipline through small daily steps that really added up. I am beyond grateful for you and your gifts and your work!! You definitely have the capacity to meet anyone where they are at and help them get to where they want to be!” Thank you, thank you, thank you!”
Alexandra B.
What Becomes Possible
When we work together, your varied endeavours stop competing for your energy and start working together as a powerful ecosystem. You move from scattered and exhausted to clear and strategic. Whether you're diversifying your income, pursuing vertical expansion, launching a creative project alongside your corporate career, or integrating multiple businesses you're already running—everything aligns. Your professional success matches your lifestyle. Work, life, and impact function as one cohesive whole. You increase your capacity to receive opportunity and abundance. You stop feeling like you're doing too much and start feeling like you're doing exactly what you're meant to do. Life becomes rich in every sense—financially abundant, deeply fulfilling, full of pleasure and presence. You live your big dreams with less burnout. way more resourced and feel seen in your way of executing.
Tools for Transformation
I do this through unique and transformational methods I've cultivated over years, professional and business expertise, and curated experiences. While I bring many tools to our work together, these methods are parts of the Keep On Dreaming Up formula:
Heart Magic
For inner clarity, awareness, alignment, feel-good rich living, expanded manifestation, and opportunity and abundance.
Turn To Gold
For building a new income path and business, expanding an existing one, or creating a hybrid approach to income.
Get Connected
A masterclass to help you create meaningful, high-impact in-person experiences for your business. Drawing on my 20 years of event curation expertise to add connection and community to your ecosystem.
A Multi-Faceted Approach
I've always had multiple things going—work, business, events, and study at any given time. Going all in on one thing works for some people, but for me it's never been attainable. I need more. The desire and pull never changed, even when I tried to fight it(also a mani-gen!). That's how I know it's wiring, not a choice.
The past few years have also taught me that diversifying income isn't just smart—it's essential in the world we're in now. But the doubt in the face of constant "niche down" advice? Very real. I've learned the hard way, but I come by this honestly.
My ability to see and support the whole of you comes from a deeply multifaceted background. I've run company operations and sales, built my own side businesses, studied modalities like Yoga and Reiki, created countless experiences—often overlapping 2 or 3 at a time. I've been a trusted support and experience creator for founders and entrepreneurs for many years.
I can spot the gaps between your energy and effort, and I'm very direct about what doesn't work. Sometimes building a sustainable ecosystem means letting go of things that don't align—even if they're "good ideas."
So I bring together:
25+ years in business management across industries, giving me practical expertise in strategy, sales, systems and operations.
20 years curating and managing experiences and events that bring people together in memorable ways.
7 years of coaching and leading group experiences and workshops rooted in the spiritual space and entrepreneurial events.
My own personal transformations that shaped the inner awareness tools I have embodied, studied, and now share.
This combination allows me to look at your entire ecosystem—not just your business or just your life, but how it all works together. I meet you with both the practical business acumen and the inner transformation tools to support aligned, sustainable success as a “I’m not just one thing” human.
The urge to create and build is intense maybe even obsessive, so it should be cup, energy and wealth filling, not depleting.
So go all in but with the right results.
Ready to Begin?
I run intimate 3-month Keep On Dreaming Up cohorts (6-8 people max) that launches quarterly. Next one will be Q2 April 2026. Each cohort includes the Dream Up Ecosystem Audit Mapping.
Not ready for the full cohort? Start with the $500 Dream Up Ecosystem Audit to see your whole picture clearly.
(This fee is waived if you join the next cohort.)
You can also book a free Dream Up Chat to explore if this work is right for you and learn about the next cohort opening.