𝗪𝗶𝘁𝗵𝗼𝘂𝘁 𝗮 𝗖𝗵𝗮𝗹𝗹𝗲𝗻𝗴𝗲 𝗡𝗲𝘁𝘄𝗼𝗿𝗸, 𝗬𝗼𝘂’𝗿𝗲 𝗕𝘂𝗶𝗹𝗱𝗶𝗻𝗴 𝗶𝗻 𝘁𝗵𝗲 𝗗𝗮𝗿𝗸

Sofia* grew up in a family that valued community service. They spent the first weekend of every month volunteering near home and a week each summer building homes abroad. Sofia also loved working with numbers. She won math honors in middle school and high school and competed in several national competitions. In college, economics and data science became her favorite courses.

She started her career in the fast-paced world of finance at a major brokerage firm where she excelled but felt unfulfilled. She appreciated being able to work heads-down and analyze large data sets, but after a few years, Sofia missed the aspect of helping others, which was an integral part of her life. Her job demanded long hours, and while she could give a few hours here and there, she often felt exhausted and unrewarded.

Once Sofia decided to leave the brokerage to pursue her true passion, creating a positive social impact, she made two key choices. First, she saved aggressively for her transition, even temporarily pausing charitable giving—a difficult decision she promised to make up for later. Second, she reached out to people to explore ways to combine her financial expertise, personality, and desire to make a meaningful difference.

Almost a year later, on her birthday, she founded Pathway to Progress, a company focused on financial literacy and empowerment for underserved communities. She structured it as a company (versus a nonprofit) to increase her options for sustainability. She wanted to create a BCorp (a certified company meeting high standards of social and environmental performance, accountability, and transparency) one day but initially wanted to focus on a double bottom line, profits and impact.

As Pathway to Progress grew, Sofia faced challenges in scaling operations while preserving her mission's integrity. She needed guidance on balancing her limited budget with increasing impact. Should she invest more in direct community programs or in building her team to create more programs? Her introspective nature often led her to overthink and become stuck in her perspective. While the problem at first seemed like another math equation, she struggled with the absence of a clear-cut answer. Sofia recognized she needed external insights to move her business forward.

She built a challenge network of individuals with diverse backgrounds and expertise. She connected with Marcus Thompson, a seasoned entrepreneur experienced in scaling social enterprises, and Dr. Rachel Kim, an expert in community development and social policy. She also brought in Ethan Lee, an extroverted marketing strategist, to help broaden her audience and increase company visibility. She had first met Marcus and Rachel during her brokerage firm days while planning her next steps.

Sofia sought advice on growth strategies and spending priorities. She explored revenue-generating opportunities that aligned with her mission, such as tutoring and personal finance classes for high schoolers. She also asked about measuring social impact and building referral partnerships with community organizations.

She asked about her dilemma of allocating limited resources to reach her goals. She also asked about ways to generate revenues that supported her mission (e.g. tutoring and classes around personal finance for high schoolers ho could pay), ways to measure social impact, and how to build referral partnerships with community organizations.

Their guidance brought specific solutions and helped her overcome her tendency to overthink, teaching her to balance reflection with action. Sofia's decision-making and leadership improved significantly through her network's feedback. As a result, her company achieved steady growth, expanding into five new communities the following year while eventually providing her with a reasonable salary. Sofia grew more confident in navigating complex challenges while maintaining her mission's integrity.

What’s a Challenge Network?

Success—however you define it—requires two essential types of people in your life.

The first type is familiar: those who support you unconditionally. These people understand your background, struggles, and intentions. When you make mistakes, they offer forgiveness before you've even forgiven yourself. Their unconditional love creates a safety net that strengthens your resilience.

The second type is equally important: those who push you to excel and explore new possibilities. This is your challenge network, a group that offers honest feedback and highlights your blind spots and areas for growth. They emphasize improving your process rather than focusing solely on outcomes, recognizing that while you can't control results, you can control your approach.

Organizational psychologist Adam Grant, who coined the term “challenger,” describes this person as follows:

“Somebody who pushes you because they

believe in you. They are not willing to settle

for something that is not your absolute best work.”

Thomas Waschenfelder puts it this way:

“Surround yourself with people who make you

believe you're capable of far more than you

think you are. This alone can change your life.”

Why Do Introverts Need One?

While every founder can benefit from others pushing them toward their best work, introverts especially need to consider forming a challenge network. Here's why:

Introverts naturally engage in deep introspection, which can lead to overthinking or becoming stuck in their perspectives. A challenge network provides fresh viewpoints and critical feedback, helping break free from limiting thought patterns and consider new ideas and approaches.

Because introverts prefer meaningful, in-depth conversations over casual interactions, a challenge network creates an ideal environment for thoughtful exchanges that match their communication style.

While large networking events can feel overwhelming, a challenge network consists of smaller, focused groups or one-on-one conversations—settings that better suit introverts' comfort levels.

Though introverts may initially find criticism difficult, a challenge network offers a safe space for constructive feedback. This feedback helps build confidence by addressing weaknesses and refining ideas in a supportive yet honest environment.

Introverts are often creative problem solvers, and a challenge network enhances this strength by encouraging them to question assumptions and explore new ideas. This process drives innovation and personal growth—crucial for introverted leaders and entrepreneurs.

"If you want to go fast, go alone.

If you want to go far, go together."

– African Proverb

Build a Challenge Network

Even experienced founders encounter new situations regularly and seek others' advice to make the best choices, especially when navigating complex decisions in unfamiliar territory.

A challenge network consists of people who provide honest, constructive feedback. They help you stay informed about emerging concepts and strategies while pushing your thinking forward—preparing you for future challenges, showing you unexpected opportunities, and preventing hidden risks.

Simply put, these are people who tell you what you need to hear, even when it’s not what you want to hear.

When building your challenge network, prioritize people with strong expertise and direct communication skills over those who are simply agreeable. Though their leadership approaches may differ from yours, they should share a commitment to your growth. Find people willing to constructively point out areas for improvement—those who can deliver honest feedback with good intentions.

Search for role models in your position, industry, and market. These might be professionals a few years ahead of you or those with decades more experience. Also, include accomplished people from outside your industry since their perspectives will broaden your approach.

Your network should include diverse backgrounds to ensure a wide range of ideas. This variety helps you avoid tunnel vision and make better decisions. Beyond different backgrounds, genders, and generations, include complementary personalities. If you're highly introverted, include several extroverts. Balance analytical thinkers with creative problem-solvers and strategic planners with practical executors. This mix ensures your ideas are examined from multiple angles.

By thoughtfully building your challenge network, you create a powerful tool for personal and professional growth that helps you navigate challenges and achieve success on your terms.

When and How to Ask for Help

As a founder, it's natural to swing between "I have it all under control!" and "I'm completely overwhelmed!" This swing may happen several times in a day. Don't wait for either extreme—be ready to learn at any point in your journey.

A challenge network helps you tackle both specific issues (like co-worker conflicts, investor communication, or leadership terminations) and broader strategic questions (such as exploring new markets, developing products, or timing your next fundraise).

Even when everything seems stable, meet with your network at least twice yearly. They might spot opportunities, trends, or risks you haven't noticed—insights you wouldn't know to seek on your own.

Before the meeting, prepare at least five questions to ask. Whether specific or general, having clear questions ensures productive and meaningful discussions.

Be honest. While you may feel pressured to project constant confidence, seeking help demonstrates strength and leads to better outcomes. Remember that everyone you meet has experienced similar feelings of uncertainty, confusion, and anxiety. Their willingness to help shows they're invested in your success.

During meetings, leverage your listening skills. Encourage advisors to share their experiences and insights and actively listen to their feedback. If their advice doesn't seem relevant, don't just wonder—directly ask how it applies to your situation. They might have made a connection they haven't fully explained yet.

If face-to-face meetings feel daunting, try video calls or email. These alternatives let you benefit from advisors' expertise while staying in your comfort zone.

After receiving advice, update your advisors on how their input shaped your decisions. This follow-up shows you value their time and strengthens your relationship.

Key Takeaway: Build a challenge network that pushes you to excel—it's essential for your growth as a leader and your business's success.

How Can I Keep Learning? Choose one person to begin building your challenge network. Reach out to them before next Friday to schedule a conversation in the coming weeks.

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* Sofia's story is a fictional account inspired by various people and situations I've encountered over the years. It was created to provide another perspective on this topic.

Build Scale Grow solves problems for fast-growing startups, specializing in Social Impact, EdTech, and Health Tech and focusing on Introverted Founders.

I wrote this post with AI editing. This is a paid stock image.

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