Side Hustle Pro

504: How to Go From Side Hustle to $1 Million | My Coaching Session with Dielle Charon

March 6, 2026

Key Takeaways Copied to clipboard!

  • Monetizable skills are most easily found in areas related to health, wealth, and relationships, or by leveraging existing work skills and hobbies. 
  • The coaching industry, despite criticism regarding sketchy marketing, is growing rapidly, and ethical practitioners should participate to elevate the industry. 
  • Moving from a six-figure income to seven figures requires significant mindset shifts, including increased visibility, overcoming people-pleasing tendencies, and claiming one's authority and identity. 
  • The primary desire for most podcast creators is to start or fund a business, making entrepreneurship the core motivation beyond just podcasting itself. 
  • Money objections in sales often mask deeper, unarticulated niche-based objections, which can be uncovered by addressing the three pillars of purchase: answered questions, inevitable results, and relatable case studies. 
  • The perceived 'steady paycheck' of a 9-to-5 job is a lie perpetuated by white supremacy to discourage Black women entrepreneurs from building their own wealth and becoming direct competitors. 

Segments

Dielle’s Background and Realization
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(00:02:58)
  • Key Takeaway: Dielle McMillan transitioned from a social worker role earning $2,500 monthly with six-figure debt because institutional work undervalued her skills and didn’t align with her desire to build a family.
  • Summary: Dielle started as a social worker at Duke University, earning only $2,500 a month despite having a Master’s degree. She quickly realized the corporate/academic structure was not sustainable due to low pay and long commutes. This realization prompted her to explore various side hustles, including life coaching and website building, to find an alternative income path.
Identifying Monetizable Skills
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(00:08:34)
  • Key Takeaway: Skills that people pay for are often found in three areas: monetizing current work skills at a higher rate, leveraging hobbies, or fulfilling requests friends and family frequently ask for help with.
  • Summary: To identify a monetizable skill, one should first consider what they already do at work and charge significantly more for it as a business. Second, hobbies present opportunities for monetization, especially for creatives. Third, frequently requested favors from family and friends often reveal an unrecognized, marketable skill set, as demonstrated by a client whose relationship advice became her coaching niche.
Coaching Industry Criticism and Growth
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(00:14:08)
  • Key Takeaway: The coaching industry faces skepticism because it is relatively new and suffers from sketchy marketing, but its continued rapid growth means ethical practitioners should join to improve its reputation.
  • Summary: The coaching industry is often criticized because it is new, similar to how Uber was initially viewed with suspicion. While unethical business practices exist, every industry has bad actors, and the upside of coaching is significant. Participants can choose to be part of the solution by providing ethical, service-based frameworks.
Overcoming Pricing Mental Barriers
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(00:18:41)
  • Key Takeaway: The belief that one’s community cannot afford high prices is countered by evidence that women of color within Dielle’s network have collectively brought in over $40 million, proving an economy exists for their services.
  • Summary: To overcome the mental block of charging high rates, entrepreneurs should recognize that their potential buyers exist across diverse financial situations, not just mirroring their own past struggles. Dielle’s clients have collectively earned $40 million, demonstrating that people are actively paying premium rates for coaching and education. Entrepreneurs must avoid inferring the entire market mirrors their personal financial constraints.
Reframing Job Security and Sales
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(00:22:52)
  • Key Takeaway: Entrepreneurship is the primary vehicle for financial safety for women of color, as jobs are designed to retain talent, not guarantee long-term security, and selling oneself to get a job is already a form of sales.
  • Summary: The idea that a traditional job provides safety is outdated, rooted in mindsets from previous generations; true financial safety comes from entrepreneurship. Furthermore, individuals already sell themselves extensively during the job application process, including resume building and networking. This existing sales muscle can be redirected to build an independent business.
Six to Seven Figure Growth Blocks
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(00:29:46)
  • Key Takeaway: Scaling from six to seven figures is often blocked by the need for increased visibility through thought leadership, overcoming people-pleasing related to growth, and identity shifts required for higher organization and creativity.
  • Summary: Growth to seven figures demands greater visibility, often requiring the production of more intellectual property and thought leadership content. People-pleasing can manifest as fear of scaling client numbers or making relationship dynamics (family, team) uncomfortable. Identity barriers arise from feeling unprepared for the increased organization or creativity needed at the next level.
Seven-Figure Business Model Simplicity
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(00:46:04)
  • Key Takeaway: A simple seven-figure business model involves five launches per year—three for the foundational beginner program and two for the advanced offer—supported by a lean team of an OBM and a coaching assistant.
  • Summary: The core seven-figure model requires five launches annually: three for the beginner program and two for the advanced offer, which can be substituted by a converting ad funnel. Overhead can remain low, requiring only the owner, an Online Business Manager (OBM) for operations, and a coaching assistant to manage client support.
Improving Sales Messaging and Positioning
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(00:51:28)
  • Key Takeaway: Sales conversion is determined by the quality of messaging and sales assets, not the frequency of execution, meaning updating a webinar slide deck for an hour is more valuable than running a poorly converting weekly webinar.
  • Summary: If sales actions are causing burnout without sufficient return, the focus must shift to improving the conversion mechanism, such as the slide deck or sales page messaging. Updates to these assets should be treated as short, focused tasks, ideally taking no longer than a week. For Nikayla’s class, the messaging needs to explicitly state the business-building goal, as the primary desire for most is entrepreneurship, not just podcasting.
Defining Podcast ‘Why’
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(00:54:02)
  • Key Takeaway: Entrepreneurship is the underlying desire for most podcast starters.
  • Summary: Listeners often seek podcasts to open career doors or start a business, with 90% wanting the podcast to serve as a marketing tool or generate revenue. The core desire is often to be an entrepreneur, not just a podcaster. Positioning must incorporate the business goal to align with this primary motivation.
Webinar Messaging Alignment
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(00:55:20)
  • Key Takeaway: Webinar messaging must address top objections like content creation uncertainty.
  • Summary: Misalignment between ad copy (e.g., ‘get paid to podcast’) and webinar content (e.g., focusing only on exit plans) can confuse prospects. A common objection is not knowing what to say, which should be addressed, even if the detailed solution is in a separate program like Podcast Moguls.
Objection Handling Strategy
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(00:59:42)
  • Key Takeaway: Money objections often hide underlying niche or belief-based barriers.
  • Summary: When price is cited as an objection, it is often a default response rather than the true barrier. True purchase triggers involve answering all questions, making belief in the result inevitable, and seeing relatable case studies. It is beneficial to hypothesize what the objection would be if money were not an issue.
Seven-Figure Growth Steps
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(01:02:16)
  • Key Takeaway: Scaling to seven figures requires optimizing current funnels before expanding efforts.
  • Summary: Next steps for growth include establishing a clear business model with defined launches and ad funnels, and hitting specific metrics. Focus should be on doubling current conversions (opt-ins and webinar sales) rather than immediately expanding activities. Cultivating the identity of being the number one educator solidifies authority.
Maintaining Business Identity
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(01:03:12)
  • Key Takeaway: Sustaining a successful identity requires constant recommitment and reviewing past wins.
  • Summary: Holding onto a successful identity involves redeciding and committing, reinforced by constantly reviewing accomplishments, from client messages to awards. This practice eventually makes the identity automatic, similar to an established personal trait like being a parent. Mindset work is continuous regardless of business success level.
Lightning Round Insights
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(01:04:56)
  • Key Takeaway: Creativity and challenging employment stability are keys to entrepreneurial success.
  • Summary: Dielle Charon recommends her journaling ecosystem for mindset work and Stacey Baiman’s series on belief for business resources. Audacity in business stems from creativity and the willingness to try new angles and solutions repeatedly. The concept of a ‘steady paycheck’ is a lie that masks the inherent risk Black women face in traditional employment.