I used to think asking for help was an admission of failure. Like, if I had to ask someone for something, it meant I was not smart enough, not capable enough, not good enough to figure it out myself.
That belief almost cost me my business.
I spent years trying to do everything alone. I did not want to bother anyone. I did not want to impose. I did not want to seem like I did not know what I was doing.
Meanwhile, I was drowning. Working 70-hour weeks. Burning out. Missing my family. All because I would not swallow my pride and just ask for help.
It took a serious crisis — and a very patient mentor — to teach me this lesson: asking for help is not weakness. It is strategy. And it might be the most important skill an entrepreneur can develop.
Why We Do Not Ask for Help
Before we get into the how, let me address the why. Because the reason most people do not ask for help has nothing to do with logic — it is almost entirely emotional.
Fear of rejection: What if they say no? What if they think less of me? What if they see me as weak?
Fear of obligation: If I ask for help, I will owe them something. I will be in their debt.
Fear of exposure: Asking for help means admitting I do not know something. And if I admit I do not know something, people might realize I am a fraud.
All of these fears are real. But they are also all, 100 percent, in your head.
Fear of rejection in business is something I address in depth — but the short version is: asking for help is not rejection. It is information. Either they can help or they cannot. Either they will say yes or they will say no. Either way, you are no worse off than you were before.
Help Is a Multiplier, Not a Crutch
One of the most damaging myths about success is the "self-made" narrative. You know the one: the entrepreneur who pulled themselves up by their bootstraps, never asked for anything, and built an empire through sheer force of will.
It is a myth. And a harmful one.
Every successful entrepreneur I know — myself included — has a long list of people who helped them along the way. Mentors who gave advice. Colleagues who made introductions. Coaches who provided perspective. Team members who handled the work we were not good at.
No one builds a significant business alone. Not one person. The fastest path to success is not figuring everything out yourself. It is finding the people who have already solved the problems you are facing and asking them for their guidance.
How to Ask for Help (And Actually Get It)
Most people ask for help badly. They send vague, open-ended requests to everyone they know: "Hey, do you know anyone who can help me with my business?"
This does not work. It is too vague. It does not give the person any specific action to take.
Here is how to ask for help effectively:
1. Be specific.
Instead of: "Can you help me with my business?"
Try: "I am trying to figure out how to price my new coaching offer. You have done this successfully — would you be open to a 20-minute call where I could ask you three questions?"
2. Make it easy to say yes.
Give them a specific, low-commitment ask. Do not ask for a months-long commitment upfront. Ask for a small interaction. A recommendation. An introduction. A 20-minute call. Once they have helped you in a small way, the relationship is established and bigger asks become easier.
3. Show you have done the work.
Do not ask for help with something you could have easily looked up or figured out yourself. Ask for help with things that genuinely require someone else is expertise, experience, or connections.
4. Express genuine gratitude.
When someone helps you, acknowledge it. Thank them specifically. And when you are in a position to help others, pay it forward. Your business will grow by asking for what you want — but it grows faster when you are gracious about receiving it.
Invest in Getting Help
Here is the mindset shift that changed everything for me: hiring help is not a cost. It is an investment with a return.
When I hired my first business coach at 25, I was making almost no money. The investment felt terrifying. But that coach helped me make my first $10,000 month within three months of working together.
When I hired my first VA to handle administrative tasks, my income went up. Because I was spending my time on the highest-value activities — the things only I could do — instead of getting bogged down in tasks that anyone could do.
Every dollar you spend on help that frees you up to do more of what you are uniquely qualified to do is an investment. And unlike many investments, this one has a near-guaranteed return.
Build Your Personal Board of Directors
I want you to identify five to seven people who serve as your informal board of directors. These are people you trust to give you honest feedback, challenge your thinking, and point out blind spots.
Some of them might be paid advisors — coaches, consultants, mentors you invest in. Others might be peers — fellow entrepreneurs at a similar stage who you meet with regularly. Others might be people further ahead than you who have agreed to be occasional sounding boards.
This is not about having cheerleaders. It is about having truth-tellers.
My board of directors has helped me avoid catastrophic decisions, see opportunities I was blind to, and course-correct before problems became crises. I would not run my business without them.
The Ask Is the Point
Here is the reframe I want you to sit with: your ability to ask for help is directly correlated with your ability to grow.
The entrepreneurs who scale the fastest are not the smartest or the most talented. They are the ones who are most willing to ask for what they need, admit what they do not know, and invest in getting the support they require.
The entrepreneurs who stay stuck are often the ones who are too proud, too independent, or too afraid to ask.
So here is your homework: what is one thing you have been trying to figure out alone that you could ask someone for help with? Send one email. Make one call. Ask one question. Today.
You might be surprised by how willing people are to help — when you ask in a way that makes it easy to say yes.
Ready to Grow Your Business?
Join Wealthy Coach Academy — my 197 dollars per month coaching program where I help you build a business that actually works. Or start with a 4.95 dollar starter class and see what happens.
Frequently Asked Questions
How do I get over the fear of rejection when asking for help?
Start by asking small. Build your confidence with low-stakes asks before you go for the big ones. And remember: asking is not rejection. Either they can help or they cannot. Either way, you are no worse off than you were before.
Who should I ask for help?
Start with people you already have relationships with — existing clients, colleagues, peers, mentors. Then expand outward. The key is to ask specifically: what do you need, who specifically might have it, and what is a reasonable ask you can make of them.
Is it okay to pay for help?
Absolutely. Hiring a coach, consultant, or mentor is one of the best investments you can make in your business. Even on limited funds, prioritizing paid help in areas where you are weakest will accelerate your growth faster than trying to figure everything out alone.
How do I ask without feeling like I am imposing?
Make your ask specific and low-commitment. Instead of "Can you help me?" try "Would you have 20 minutes to answer three specific questions about [topic]?" Most people are happy to help when the ask is clear and bounded.
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About Jeremiah Krakowski
Jeremiah Krakowski is a coaching business mentor who helps coaches, course creators, and consultants scale from $3k/mo to $40k+/mo using direct response marketing, AI systems, and proven frameworks. He runs Wealthy Coach Academy and has 23+ years of experience in digital marketing. Learn more →