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Judy Goldberg on What I Learned From My Solopreneur Journey


Judy Goldberg is the Founder of Wondershift, and Author of Wake Up and Wondershift and is an inspirational solopreneur. We're grateful to have had the chance to sit down and share insights from their solopreneur journey on The Industry Leaders.


Could you begin by telling us about your background, what led you to become a solopreneur, and what specific industry or niche you've carved out for yourself?"

For six years, I taught both in the states and in Costa Rica. During my time as an educator I was introduced to two philosophies which shaped my views on human intelligence and the way we learn.


1. Howard Gardner's theory of multiple intelligences, which challenges the traditional view of intelligence as a single, monolithic entity measured by IQ tests. Gardner's theory suggests that there are multiple distinct types of intelligence, each representing different ways in which individuals can be intelligent.


2. The International Baccalaureate (IB) methodology which is designed to foster international-mindedness, critical thinking, and inquiry-based learning. This methodology aligned to my values, and I observed my students to be open-minded, reflective, caring, and equipped to succeed in a globalized world. The two methodologies reshaped my views on human intelligence and the way we learn. Since then, my career has been dedicated to creating dynamic and interactive learning experiences, synthesizing research, and imparting valuable skills and knowledge. After my tenure in education, I transitioned to the corporate sector, where I effectively applied these principles to enhance the performance of leaders and teams. Twelve years later, during a bike ride at the gym, I read a powerful quote, which made me realize I was ready to set up my own business and share my talents with more than one company at a time. The powerful words that lit me on fire? “A year from now, you will wish you had started today.” Rooted in humanity, Wondershift offers clients a unique combination of expertise and deep care. I provide research-based tools with experiential opportunities that hold people at the edges of their discomfort - all as a means to unlock new thinking, strategies, ways of working and growth. My unique combination of talents allows my clients to grow in the moment in ways that engender lasting change. Wondershift brings learnings from a myriad of industries and I believe that benefits all partners. Therefore, I do not tie the company to any specific industry or believe in a one-size-fits-all approach.


Starting a business is often a leap into the unknown. In your early days as a solopreneur, what were some unexpected challenges you faced, and what strategies did you develop to overcome them?

So many! Technical Challenge: After spending 10 hours working on a new program that I was quite proud of, my computer crashed. This was back in the day when automatic save was not an option. Lesson learned, backup your computer and then back it up again. Perfectionism Challenge: My confidence internally was strong with people who knew me and my capabilities so well. With new clients who did not know me at all, I sometimes froze and came up against time crunches because I did not want to share an ‘unfinished’ product. When I switched to a partnership model I shifted my whole approach. By collaborating with others, I learned you don't have to get it right, you just have to get it going. Launch it, adjust it, and share in the process as a way to build connections and a better product. Intellectual Safeguarding Challenge: I took pride in the thoroughness of my proposals, often outlining specifics for clients of what a session may look like. After sharing my proposal and meeting with a new client to answer their many questions, I noticed they were taking copious notes, almost word for word as I described the session I had designed. This seemed a bit strange. They called me after and said, “Thank you, we are going to do this internally instead of hiring an external facilitator.” I came to find from an inside source that they used my ideas and session flow. From now on, I trust my gut. If something feels right, it probably is. If it doesn’t, it probably isn’t. It’s that simple. And I do not include as many details in my proposals.


Can you share a pivotal moment where you realized that your unique approach was actually working? What did you learn from that experience, and how did it shape your journey?

I remember the first time I introduced Archetype Cards as a tool to visualize the future to a leadership team in the Netherlands. It was a team of skeptics who scoffed at first and asked me why I brought Tarot Cards to their strategy meeting. My relationship with a few of them was strong so I laughed it off and asked them to be open and engage in the session. If they deemed the day useless, they could tell me at the end of the day. They loved every minute, participated in fresh dialogue, engaged in spirited debates, and challenged each other regarding their aspirations for the future and the archetypes that would need to be activated to get there. As the day came to an end, they wanted to continue the conversations over dinner and cascade a similar session with their entire team. I learned to trust my experience and instincts and to be more aware of why resistance may surface and how to respond and move through it with the person in partnership.


Your success hasn't come overnight. Could you delve into the key principles and practices that you've found most critical in building your business as a solopreneur? What differentiates your method from others?

The key principles and practices that I’ve found to be most critical in building my business are centered around values, curiosity, mindset, and staying awake. Let me explain each a bit more in detail. Values. I put in the work, thought, and time to define my personal and business values and I live true to them every day. They inform the decisions I make, the clients I take on or don’t, what I stand for, and how I operate my business. And I have a trusted circle who keeps me honest in moments when I need a gut or accountability check. Curiosity. This trait led me to a role at Discovery Channel, a company known for fostering curiosity since its inception by John Hendricks in the '80s. Curiosity is intrinsically tied to asking questions, exploring “what if…”, and suspending judgment and has fueled my creativity and business. It's driven me to delve deeper into perceived challenges, adapt readily to new perspectives, expand my network beyond expectations, and inspire critical thinking from diverse viewpoints. Mindset. One catch phrase you may hear from me often is, “Mindset Matters”. It matters greatly. It can improve, hinder, or transform your day. During the first year of launching my business I adopted a monthly mantra that I repeated daily.


These mantras effectively countered negative thoughts by redirecting my attention and energy to my strengths and what was possible. Today I concentrate on applying three specific mindsets: growth, beginner’s mindset, and abundance. Staying Awake. This doesn't imply sleep deprivation. Staying awake involves staying current and well-informed about global events, my clients' industries, and more. Through reading, listening, observing, conducting research, and taking notes, I demonstrate my value as a connected and knowledgeable partner to the leaders I collaborate with. Perhaps my differentiator is best said by a client, “You have a multiplier effect. You’re prepared and well researched and articulate and you have a sense of generosity and playfulness and curiosity that is infectious and inspires confidence and connection. I am drawn to partnering with you and appreciate how effective you are with me and the team.” I truly see wonder in the every day. I apply that sense of possibility to everything I do, and foster it in myself, my business, and with my clients. It is a bedrock of who I am, how I behave, and how I see the world, and I believe it differentiates me from others who are just offering services.



Running a business solo requires a blend of skills. How have you balanced the demands of various roles like marketing, product development, and customer service? Can you share any tools or strategies that have been particularly effective?

I became a certified Practitioner of David Allen’s methodology, Getting Things Done (GTD) before launching WonderShift, and owe much of my success to the GTD framework and core principles. One key practice is the importance of getting tasks out of my head and into a trusted system. This reduces mental clutter, alleviates stress, and allows for greater mental clarity and focus. Other tools and strategies: Prioritizing an AGM (Annual General Management) Meeting with an accountability partner. For 8 years straight, my solopreneur friend, Sophie, and I come together for 4-6 days to review a two-page business agenda that covers everything from goals, a values check, financials, stop-start-continue exercise, contract and pricing review, mental and physical wellbeing, and so much more. I am more conceptual and visionary, and she is more structured and detail oriented, so we can challenge and stretch each other in every aspect of our business. We have both seen year-on-year growth and both believe our AGMs are key to our success. Build and maintain a strong network. 95% of WonderShift’s business comes from my network. Prior to launching WonderShift, I invested time and energy into building strong relationships with peers and leaders at both Discovery and Sony Pictures. These colleagues knew my areas of expertise and built a strong word-of-mouth marketing engine for WonderShift. That engine, combined with connections across my field of leadership, Organizational Design, strategy, and coaching have granted me an abundance mindset, shared resources, and accountability partners. Amazing accountants who keep me honest, educated, and interested in all of WonderShift’s financials. The company I hired is a women owned business, which aligns with my values to uphold and promote women and marginalized persons. Operational Advantage.


As a solopreneur, I don’t have an IT or support infrastructure. So finding systems to solve various business challenges is critical. For instance, Evernote is the best for note taking for me. Easy to search, categorize, organize, share when needed with my assistant and others who I bring into projects. And Canva! I cannot rave enough about Canva and what it offers for me to create professional materials, marketing content, visuals, etc. It takes time to get stuck in and learn about the many features and is worth every minute. As I evolve my business, offerings, and products I am still learning how to best wear all the hats needed to run a business, what to do when I mess up, and how to celebrate even a small success.


Reflecting on your journey, what's one lesson you learned the hard way that you wish you had known when you first started? How would you advise other aspiring solopreneurs?

Dig into the Money - what you have, what you need, what will make you nervous, what will make you breathe easy, the payment terms you agree to, the process to get paid. In the beginning there is excitement when signing with your first few clients. You sign an NDA, a contract, you share a proposal, and you get on with delivering on the outcomes you promised. Then you get paid. Well, not exactly. You send the invoice and are told it needs to go to a different person or via their internal system or needs a PO number that someone forgot to submit. The list goes on as do the weeks or months until you get it sorted. All to say, just because you do the work does not mean the money will come in when you think it will. This was my first lesson in invoicing and payment terms, and I soon realized that there were going to be months when I was not going to make any money, which is very scary! If you are an aspiring solopreneur, here is what I would advise based on my experience: - Review your invoicing process: Ensure that your invoices are clear, accurate, and include all necessary information; payment terms, contact information, required references, PO #s.


- Clarify payment terms upfront: Ask so that you can be crystal clear about payment terms, specific internal approval processes or PO numbers, etc. Ask to invoice half up front and half at the end of an engagement if you need to. And be clear about your own needs, parameters, and payment boundaries.


- Use invoicing software: I now use Xero.com to automate my invoicing, to send reminders for overdue payments and track payment status.


- Include late payment penalties: Include clauses in your contracts or invoices that outline consequences for late payments, if you feel this is helpful.


- Have a cash reserve: There may be months with delayed payments; it's wise to establish a cash reserve or emergency fund to ease any nervousness caused by delayed payments.


- Follow up promptly: If a payment is delayed, follow up. It could be a mistake, human error, or glitch in the system. Always be professional in communication throughout the process.


- Charge what you’re worth: Match the work and energy with a price point that merits your involvement and shows you value yourself. If getting paid becomes a real issue for you seek legal advice to ensure you protect your rights and interests.


Innovation is often key in entrepreneurship. How have you fostered creativity and innovation in your business? What tips can you offer to those seeking to continually innovate in a rapidly changing market?

My best tip is to be curious. It is one of the core values I hold most dear, and has pushed me the farthest in my personal and professional journey of discovery. Brian Grazer, author to A Curious Mind: The Secret to a Bigger Life said, “Curiosity is the tool that sparks creativity. Curiosity is the technique that gets to innovation.” I believe this to be true. Specifically, my curiosity drives me to examine the impact of the micro moments, apply inverse and reverse thinking, take field trips to understand the way things work (e.g., sound studio, a canning facility, glassblowing workspace, 3D printing lab, etc.), engage in interactive digital art exhibits, talk to strangers, and so much more. This means I’m ALWAYS learning and growing, flexing my discomfort and stretching my brain. When I remain curious and connected, my business does too. For example, I recently released “Wake Up and Wondershift”, a new - and I think, rare - book designed to guide people to uncover blocks, build awareness, and achieve their desired shift in business or life. The very intentional design fosters curiosity, flexibility, growth, mindset, and repeated engagement - all things I know to be keys to lasting transformation. In addition, I’m working on the Wondershift experience - a unique and innovative five-month immersion designed for people ready to commit to a new vision for their lives.


Looking forward, what are your plans for the future of your business, and how do you see the landscape for solopreneurs evolving in the next five years?

My plans for the future of Wondershift are to:


- Launch the 5-month Wake Up and Wondershift journey.


- Test out and learn about 1-2 new technologies each quarter to determine what might have an impact on me and my business: AI tools, Cybersecurity tools and practices, Data Visualization tools, Augmented reality, etc.


- Build a stronger online presence with a focus on my new book, Wake Up and Wondershift and by providing insights and exercises for people to make their desired shift in life. A Wake Up and Wondershift series may also be in the future. Stay tuned!


- Collaborate with global peers to diversify income streams with new products and services.


- Continue to read, learn, commit to professional development to expand knowledge and skills. In the next five years:


- Data will continue to be an area of focus for most companies, and because most things are tracked, I think solopreneurs will be tracked as well. Perhaps there will be ratings and reviews for each solopreneur like restaurants do on Yelp looking at the whole person, not just the work you deliver. This will go beyond the testimonial and could get tricky.


- Health and wellbeing will remain top of mind so anything a solopreneur can do to support wellness, emotional intelligence, and values-based leadership will be paramount, and will elevate the provider above those who are using data in a vacuum.


- Niche products and services seem to be sought after, so specialized solopreneurs will do well. Because the landscape is changing, I think Solopreneurs…


- Need to be clear on their core values.


- Should be able to describe how they adhere to ethical and sustainable practices.


- Know the causes they care about and why.


- Will need to be more flexible with pricing to adapt to economic changes.


For those who want to know more about you, your work, or perhaps even become a client or collaborator, how can they best get in touch or follow your journey?



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