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The Shame That’s Costing You $100K (Why Successful People Struggle to Ask for Help)

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Are You Losing Six Figures to Founder Shame?

Let me tell you about a client I coached last year: a founder who ran a creative agency out of Brisbane.

She’d built her business from freelance gigs into a thriving team of 12, serving wellness, hospitality, and lifestyle brands. Revenue was nearing $1.5 million, and she’d just moved into a sunlit office in West End. 

On paper, it was a dream.

But behind the scenes, she was overwhelmed. 

Not by workload or cash flow but by the weight of going it alone. 

She made every big decision in silence. No strategy talks with her team. No calls to fellow founders. No honest conversations, even with her partner. She just kept smiling, kept working, kept pretending she had it under control.

Then came the pricing change.

One night, after seeing a post about “value-based pricing” on Instagram, she decided to double her entry-level retainer and cut lower-margin services. 

With ZERO testing and NO real client input. 

Just a solo decision made in isolation.

Three weeks later, four clients left, quietly. 

One said, “We still love your work, but it’s no longer in our budget.” 

Another didn’t renew.

She assumed she’d misjudged the market. What she didn’t know? Two of those clients would’ve stayed for a mid-tier option. 

One later told a mutual contact, “I wish she’d just asked us how we felt.”

That single decision cost her $112,000 in annual revenue.

And the worst part? 

She didn’t tell anyone. Not her team, not a mentor until many months later when she approached me with this problem. 

When she finally did, she said, “I felt like a fraud. I call myself a strategic thinker, but I made a six-figure mistake because I didn’t talk to anyone.”

But she wasn’t a fraud.

She was trapped in what I call success shame, the belief that because you’ve made it this far, you should have all the answers. That asking for help means you’re not cut out for this.

In Australia, where the “quiet achiever” myth runs deep, that shame is even stronger. 

We’re taught to tough it out, not reach out.

But you know what?  

“The most expensive advice is the advice you don’t get.”

Every untested assumption, every silent struggle, every decision made alone it’s a leak in your foundation. 

And over time, those leaks sink your ship. It’s the gap between the leader you project and the person underneath who’s just trying to keep up.

But what if the bravest thing you could do isn’t pushing through but finally saying, 

“I don’t know. Can someone help me?”

Because that’s not a weakness.

It’s the smartest strategy you’re not using.

Isolation: The Silent Success Killer And the Strategic Cure

Let me share another story. This one about a client I worked with in Perth.

He ran a digital marketing agency focused on local service businesses plumbers, electricians, HVAC companies. He’d built a strong reputation for delivering leads, and his team of seven was tight-knit and efficient. Revenue was steady at $900K, but he felt stuck. He wanted to scale to $2M, but every time he tried to raise prices or expand his offer, something went wrong.

Last year, he decided to launch a new premium package: a six-month growth accelerator for high-potential clients. He spent weeks building the offer, crafting the messaging, designing the funnel. He didn’t run it by anyone, not his team, not a peer, not even a past client.

He launched.

Three people signed up. Two churned within eight weeks. One left a Google review saying, 

“Felt more like a sales pitch than a service.”

He was crushed. But instead of pausing to reflect, he doubled down. Hired a new sales lead. Pushed harder on outreach.

Six months later, burnout hit. He took a two-week break and came back to find two more clients had quietly left, and his team was disengaged. Morale was low.

When we started working together, the first thing he admitted was: 

“I don’t talk to anyone about the real stuff. I feel like if I show doubt, it’ll spread to the team.”

That’s the myth so many agency owners believe: that leadership means being the rock. The one who never wavers. The one who absorbs the pressure so others don’t have to.

But most of them don’t realise that isolation doesn’t protect your team.

It hurts them.

Because when you make decisions in a vacuum, you don’t just risk financial loss but you erode trust, create misalignment and slow down growth.

And the data confirms it. A 2023 study of 450 Australian small business owners found that those who made major decisions without external input were 3.2x more likely to experience preventable revenue loss. 

The average cost: $108,000 per year.

And as per the same study, agency owners who actively sought advice from peers, mentors, or advisory groups made 47% fewer costly mistakes and grew 2.4x faster over 18 months.

Because help-seeking isn’t about filling knowledge gaps.

It’s about stress-testing your thinking.

It’s the difference between launching a new offer because you think it’s good and launching it because three other founders have tried it, failed, and told you exactly what to avoid.

But so many agency owners avoid this not because they don’t need help but because they’re afraid of how it will be perceived.

They worry: If I ask for help, will people think I’m not capable?

The most respected leaders I’ve worked with aren’t the ones who have all the answers.

They’re the ones who know which questions to ask and who to ask them to.

And that’s not a weakness.

That’s leverage.

Strategic Help-Seeking: The 4-Step Shame Elimination Framework

Let’s get practical.

Over the past eight years, I’ve worked with dozens of Australian agency owners to break the cycle of isolation. What I’ve learned is this: shame doesn’t disappear with motivation. 

It dissolves with structure.

Which is why I developed the Shame Elimination Framework: a four step system designed to turn help seeking from a source of anxiety into a repeatable, results driven practice.

This isn’t about random networking or vague mentorship. It’s a strategic advisory system built on behavioural psychology, founder-specific pain points, and measurable outcomes.

Let’s walk through it.

Step 1: Strategic Advisory System

The first step is clarity. Most agency owners don’t know where they’re blind. They assume they’re weak in sales or delivery, but the real gaps are often deeper like decision fatigue, client expectation management, or operational scalability.

That’s why the foundation of this framework is the Capability Gaps Assessment. It’s a diagnostic process that maps your strengths against the core competencies required at your current stage of growth.

For example, an agency scaling from $700K to $1.5M needs different skills than one going from $200K to $700K. The former requires team leadership, financial forecasting, and client retention systems. The latter needs lead generation, service packaging, and delivery consistency.

By identifying where your capabilities don’t align with your stage, you uncover the real reasons you’re stuck.

Once you know your gaps, you can build a targeted advisory circle using three archetypes:

  • Peer Advisors: Founders at a similar stage or in adjacent niches. They don’t give answers, they ask the right questions.
  • Expert Advisors: Specialists in areas like finance, legal, or client onboarding. They provide clarity, not opinions.
  • Accountability Partners: Trusted individuals who hold you to your commitments. They don’t care about your title, they care about your follow through.

This isn’t about collecting mentors but about curating a strategic support system tailored to your specific challenges.

Step 2: Vulnerability Practice

Now, let’s talk about the hardest part: actually asking for help.

Most agency owners don’t avoid advice because they don’t need it, they avoid it because they don’t know how to ask without feeling exposed.

That’s where the Vulnerability Practice comes in. It’s not about emotional dumping. It’s about creating structured opportunities to share challenges in a way that feels safe and productive.

So, here’s how it works: once a month, you gather your peer advisors for a 90-minute session. 

Nobody wastes time here…

Instead, each person shares one challenge using a simple format:

  • Here’s what I’m facing.
  • Here’s what I’ve tried.
  • Here’s where I’m stuck.
  • Here’s the kind of help I need.

This ritual normalises struggle. It turns help seeking into a habit, not a crisis response. Over time, the shame fades because everyone is doing it.

Psychologically, this leverages social proof when people see others being vulnerable, they feel permission to do the same. It also reduces the fear of judgment by making support a two-way street.

Step 3: Cost of Isolation Calculator

If you want to eliminate shame, you need to make the cost of silence visible.

The Cost of Isolation Calculator is a simple tracking tool that logs every major decision you make whether you sought advice or not and measures the outcome.

For example:

  • Decision: Launched new service tier.
  • Advised:  No.
  • Result: Low uptake, 3 clients churned.
  • Estimated savings if advised: $45K (based on peer feedback on pricing structure).

Over time, this creates a running tally of how much isolation is costing you. One client calculated he’d lost $190,000 in 14 months by going solo on key hires, pricing changes, and client negotiations. The numbers shifted his mindset from “I should’ve known better” to “I now have proof that asking works.”

This tool is rooted in loss aversion and people are more motivated to avoid loss than to achieve gain. When you see the real cost of silence, the fear of asking fades next to the fear of losing more.

Step 4: Expertise Exchange Protocol

Finally, we address the unspoken barrier: reciprocity.

Many founders hesitate to ask for help because they feel like they’re taking, not giving. The Expertise Exchange Protocol fixes that by turning advice into a two way value loop.

When you ask for help, you also offer something in return. Not money, or favors, but your unique expertise.

Maybe you’re great at client onboarding. You trade that for help with team culture. Maybe you’ve cracked retention for service based agencies. You exchange that for financial forecasting insights.

This isn’t bartering. 

It’s value-based reciprocity. 

It activates the principle of reciprocal altruism when people receive help, they’re more likely to give it. Over time, your network becomes a self-sustaining ecosystem of mutual growth.

And giving advice isn’t just generous but it’s strategic. Teaching forces clarity. Explaining your process reveals blindspots. And the more you give, the more you’re seen as a thought leader, which attracts even better support.

Each of these steps is designed to be stage appropriate. Whether you’re pre-revenue or scaling past $2M, the framework adapts, ensuring you’re not just getting help but the right kind of help at the right time.

From Isolation to Impact: The Founder Who Broke the Shame Barrier

Remember the client I told you about earlier?

When we started working together, she admitted: “I don’t talk to anyone about the hard stuff. I feel like if I show uncertainty, it’ll make me look weak.”

We started with the Capability Gaps Assessment. It revealed her biggest blindspot: client expectation management. She was great at delivery, but poor at setting boundaries and communicating value.

So she built her advisory circle:

  • A peer founder in Melbourne who’d scaled a similar agency.
  • A finance expert who’d worked with creative businesses.
  • An accountability partner who challenged her assumptions weekly.

At her first Vulnerability Practice session, she shared how overwhelmed she felt. She expected judgment. 

Instead, her peer said, “I was there two years ago. Here’s what changed for me.”

That moment cracked something open.

She implemented the Cost of Isolation Calculator and tracked her decisions for 10 weeks. 

And everything changed after that.

She paused a rebrand project after her finance advisor pointed out cash flow risks. She revised her pricing model after her peers shared what worked in their market.

She also launched the Expertise Exchange Protocol where she offered her client communication templates to a fellow founder. In return, she got a referral to a fractional COO who helped streamline her operations.

The outcomes weren’t just financial.

She felt lighter, super confident and more connected.

And she reclaimed the $100K she’d been losing annually and grew revenue by 18% in the next quarter.

But the real win was internal. 

The shame was gone. In its place was a new belief: Asking for help is how I lead.

Building Your Strategic Support System

You don’t need to wait for a crisis to start.

Here’s your step-by-step plan to build your own strategic support system starting today.

#1 Run the Capability Gaps Assessment

Use a simple template. List the 8–10 core competencies for your stage: things like client retention, team leadership, pricing strategy, financial planning. 

Rate yourself from 1 to 5 on each. 

Then, ask one trusted advisor or team member to rate you independently. 

Compare the results. The gaps are your priority areas.

#2 Recruit Your Three Advisor Archetypes

Start small. One peer, one expert, one accountability partner.

  • Peers: Join founder communities like Founders Institute, local CEO groups, or industry-specific networks. Look for people slightly ahead of you.
  • Experts: Use platforms like Intro.co, LinkedIn, or professional associations. Be specific: “I need someone who’s scaled a creative agency past $1M.”
  • Accountability: This can be a coach, a therapist, or a founder friend with high integrity.

#3: Launch Your Vulnerability Practice

Pick a date and invite your peers. 

Set the agenda: one challenge per person, 15 minutes max. 

Use the four-part format and keep it focused. After each share, the group responds with questions with only no advice unless asked.

Do this monthly. Track how your confidence and decision quality improve.

#4: Set Up the Cost of Isolation Calculator

Create a simple log:

  • Date
  • Decision
  • Advised? (Yes/No)
  • Outcome
  • Estimated financial impact
  • Lessons learned

Review it every quarter and watch the pattern emerge.

#5: Activate the Expertise Exchange Protocol

Identify your top three areas of expertise. 

Write them down. 

When you ask for help, offer one in return. 

Like…
“I’m struggling with client retention. I’d love your input. In exchange, I can share my onboarding process that reduced early churn by 40%.”

Track the ROI and measure the reduction in costly mistakes. 

Notice the shift in your mindset.

Mastery by Asking

Let’s recap.

You don’t have to lose six figures to silence. You don’t have to carry every decision alone. You don’t have to choose between being strong and being supported.

The most successful agency owners aren’t the ones who never struggle.

They’re the ones who know how to turn struggle into strategy.

By building a support system, you’re not admitting weakness.

Instead, you’re creating an unfair advantage.

You’ll make smarter decisions, reduce costly mistakes and grow with confidence.

And you’ll finally break free from the shame that’s been holding you back.

So here’s your challenge:

Today, identify one decision you’ve been sitting on. 

One thing you’re unsure about and reach out to one person.

Ask for their input and see for yourself why you should have done this earlier.

Then come back and tell me what happened.

Because the bravest thing a founder can do isn’t going it alone.

It’s reaching out and changing everything.


Frequently Asked Questions

Q1. Can’t I succeed without a support network?

It’s possible to achieve initial success on your own, but long term growth becomes significantly harder without guidance. Most founders who scale sustainably do so with the help of trusted advisors. A support network doesn’t replace your leadership but it sharpens it.

Q2. What if my vulnerability is used against me?

This is a valid concern, which is why it’s important to be selective about who you share with. True peers and advisors value honesty and confidentiality. If someone disrespects your openness, they’re not the right person to be in your circle.

Q3. How do I find the right advisors if my network is small?

Start by joining one trusted community: like a local founder group, industry association, or online mastermind. Look for people slightly ahead of you. Reach out with a simple, genuine message about wanting to exchange insights. 

Strong networks grow from small, intentional steps.

Q4. Isn’t this just another time-consuming process?

Only if done poorly. When structured correctly, help-seeking saves time. One 30-minute conversation can prevent weeks of mistakes. The goal isn’t more meetings, it’s better decisions with less effort over time.

Q5. How do I measure the ROI of getting advice?

Track decisions before and after seeking input. Note the outcome, time saved, and financial impact. Over three months, you’ll see patterns, fewer mis-hires, faster launches, stronger client retention. The ROI shows up in reduced waste and increased confidence.

Q6. Will successful people really admit when they need help?

Yes, privately, most do. The difference is they’ve learned that asking for help isn’t weakness, it’s strategy. The most effective leaders don’t have all the answers. 

They know where to find them.

Tshimologo Leburu

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