When to Stop Figuring It Out Alone: The Case for Coaches, Mentors & Masterminds
Felicia Wright knew how to educate children. She had taught in the Clark County School District, homeschooled her own children, tutored families, and built a microschool around what parents said they needed.
Then she became an employer.
Running The Learning Outpost required more than designing meaningful learning experiences. Felicia had to manage bookkeeping, use QuickBooks, and pay employees correctly. The mission had not changed, but the decisions surrounding it had.
“You got the education down, but you got tolearn the business side,” she explained.
Through SPN’s LaunchPad Innovation Ecosystem, advisors visited her school and offered targeted feedback. Felicia later began working with me as her business coach and strategic advisor. In describing that period, she connected our work to practical responsibilities that were new to her as an educator, including QuickBooks and payroll.
Know When Resourcefulness Is No Longer Enough
Her experience illustrates an inflection pointI have seen repeatedly across nearly three decades of working with founders and leaders: resourcefulness can get an idea started, but it cannot make one person proficient in every discipline the organization will eventually require.
The useful question is not simply, “Do I need help?” It is, “What kind of outside perspective does the decision in front of me require?”
Match the Help to the Decision
Founders often begin with the person who is most accessible or encouraging. That may feel productive, but the wrong kind of counsel can leave you with more ideas and no clearer decision. Start by naming the function that is missing.
If the outcome is clear but you do not know how to execute it, you likely need a technical specialist. Bookkeeping, payroll, legal compliance, technology, and facility requirements usually call for defined expertise, not general advice.
If you are entering terrain someone else has already crossed, a mentor can help you anticipate what lies ahead. The mentor’s value is not having your answer. It is recognizing the difference between a normal difficulty and a costly detour.
If the constraint involves how you are seeing, deciding, delegating, or leading, a coach may be more useful. Good coaching does not transfer ownership of the decision. It exposes assumptions, recurring patterns, and tradeoffs so you can exercise better judgment.
A practitioner peer or mastermind serves another function. It gives you access to people building under comparable conditions. Peers can challenge the belief that your experience is unique and show you how others are approaching similar decisions.
Participants in the LaunchPad InnovationEcosystem mastermind I facilitate have described this value in practical terms. Eddie Kornegay, executive director of the Center for Poverty Solutions, reported that the mastermind became part of his day-to-day management process. He connected it to executing a 90-day plan, launching the Center’s project, and building infrastructure around the work. Arianne Craig Jolla, founder of CA$HAcademy, described a different result: “I’ve begun to consistently test the assumptionsI have about myself and my business.”
Some problems call for neither a coach nor a peer. If a rule, agency process, or public system is constraining your model, consult a policy or legal expert. If the problem requires several organizations to contribute different capabilities, you may need an ecosystem partner or convener. That distinction is important: outside guidance strengthens the founder’s judgment; an ecosystem mobilizes capabilities beyond what one founder can provide.
Choose Counsel That Strengthens Your Judgment
The title matters less than the function. Ask whether you are missing an answer, a skill, perspective, accountability, access, or a relationship. Notice whether this is an unfamiliar task or the same problem returning in different forms. Decide what you should be able to see, choose, or do differently after receiving counsel.
That expectation should shape whom you choose. Does this person understand the conditions in which you are building? Will they challenge your assumptions without taking the work away from you? Will their involvement strengthen your judgment or make you increasingly dependent on theirs?
Do not wait until everything is visibly breaking. Choose one decision you have been carrying for too long. Write down what is missing, then seek the person whose experience, perspective, or access matches that need.
Good counsel should leave you more capable ofleading after the conversation is over.
Amanda Pascale is a strategic growth partner and founder of Lionhearted Enterprises, where she advises founders and CEOs navigating consequential growth and building the organizational capacity for what comes next. Her 25-year career spans business, entrepreneurship, public policy, philanthropy, and social impact.
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When to Stop Figuring It Out Alone: The Case for Coaches, Mentors & Masterminds
7 min read
Felicia Wright knew how to educate children. She had taught in the Clark County School District, homeschooled her own children, tutored families, and built a microschool around what parents said they needed.
Then she became an employer.
Running The Learning Outpost required more than designing meaningful learning experiences. Felicia had to manage bookkeeping, use QuickBooks, and pay employees correctly. The mission had not changed, but the decisions surrounding it had.
“You got the education down, but you got tolearn the business side,” she explained.
Through SPN’s LaunchPad Innovation Ecosystem, advisors visited her school and offered targeted feedback. Felicia later began working with me as her business coach and strategic advisor. In describing that period, she connected our work to practical responsibilities that were new to her as an educator, including QuickBooks and payroll.
Know When Resourcefulness Is No Longer Enough
Her experience illustrates an inflection pointI have seen repeatedly across nearly three decades of working with founders and leaders: resourcefulness can get an idea started, but it cannot make one person proficient in every discipline the organization will eventually require.
The useful question is not simply, “Do I need help?” It is, “What kind of outside perspective does the decision in front of me require?”
Match the Help to the Decision
Founders often begin with the person who is most accessible or encouraging. That may feel productive, but the wrong kind of counsel can leave you with more ideas and no clearer decision. Start by naming the function that is missing.
If the outcome is clear but you do not know how to execute it, you likely need a technical specialist. Bookkeeping, payroll, legal compliance, technology, and facility requirements usually call for defined expertise, not general advice.
If you are entering terrain someone else has already crossed, a mentor can help you anticipate what lies ahead. The mentor’s value is not having your answer. It is recognizing the difference between a normal difficulty and a costly detour.
If the constraint involves how you are seeing, deciding, delegating, or leading, a coach may be more useful. Good coaching does not transfer ownership of the decision. It exposes assumptions, recurring patterns, and tradeoffs so you can exercise better judgment.
A practitioner peer or mastermind serves another function. It gives you access to people building under comparable conditions. Peers can challenge the belief that your experience is unique and show you how others are approaching similar decisions.
Participants in the LaunchPad InnovationEcosystem mastermind I facilitate have described this value in practical terms. Eddie Kornegay, executive director of the Center for Poverty Solutions, reported that the mastermind became part of his day-to-day management process. He connected it to executing a 90-day plan, launching the Center’s project, and building infrastructure around the work. Arianne Craig Jolla, founder of CA$HAcademy, described a different result: “I’ve begun to consistently test the assumptionsI have about myself and my business.”
Some problems call for neither a coach nor a peer. If a rule, agency process, or public system is constraining your model, consult a policy or legal expert. If the problem requires several organizations to contribute different capabilities, you may need an ecosystem partner or convener. That distinction is important: outside guidance strengthens the founder’s judgment; an ecosystem mobilizes capabilities beyond what one founder can provide.
Choose Counsel That Strengthens Your Judgment
The title matters less than the function. Ask whether you are missing an answer, a skill, perspective, accountability, access, or a relationship. Notice whether this is an unfamiliar task or the same problem returning in different forms. Decide what you should be able to see, choose, or do differently after receiving counsel.
That expectation should shape whom you choose. Does this person understand the conditions in which you are building? Will they challenge your assumptions without taking the work away from you? Will their involvement strengthen your judgment or make you increasingly dependent on theirs?
Do not wait until everything is visibly breaking. Choose one decision you have been carrying for too long. Write down what is missing, then seek the person whose experience, perspective, or access matches that need.
Good counsel should leave you more capable ofleading after the conversation is over.
Amanda Pascale is a strategic growth partner and founder of Lionhearted Enterprises, where she advises founders and CEOs navigating consequential growth and building the organizational capacity for what comes next. Her 25-year career spans business, entrepreneurship, public policy, philanthropy, and social impact.