Why Entrepreneurs Shouldn’t Be Afraid to Ask for Help

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The following is adapted from “Mr. Monkey and Me: A Real Survival Guide for Entrepreneurs” by Mike Smerklo. Copyright 2020 Lioncrest Publishing.

In addition to getting the help you need and gaining perspective from your peers, there’s an added, less obvious benefit to asking for help. Odd as it may sound, asking someone for help endears you to the person you ask, because it builds the helper’s self-esteem and makes them feel useful. People like helping. It makes them feel important, and who doesn’t like that?


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When you ask a friend or mentor for input and they give you help, their accomplishment creates a feeling of euphoria they will associate with you, creating a halo effect.

So, even though it may seem counterintuitive, numerous studies have been done to prove that asking for help is one of the most effective ways to inspire positive feelings and build relationships.

Now when I have an issue to resolve, I typically ask four to five people for help. By asking for help, I’m frequently able to accelerate solutions and growth at levels I wouldn’t have thought possible, and I’m strengthening my relationship with my network, as well.

Mike Smerklo
(Author Mike Smerklo)

Being a great leader and entrepreneur takes courage, confidence and the willingness to achieve what others have not been able to accomplish in the past. It also means knowing you’re going to make a bunch of mistakes, and being more than just “OK” with it. However, without self-awareness and a willingness to ask for help, I would wager that your chances of success are significantly lowered.

Asking for help while you’re striking out on your own as an entrepreneurial trailblazer might sound counterintuitive in some ways. The world likes to tell the story of entrepreneurs who have a “magic touch” that turns every idea to gold. But the reality is that everyone needs help, and you need to find the help that will move the needle most for you.

Here is my list of what worked for me, but this isn’t as a definitive list. Learning how to get the help you need doesn’t happen by checking off items someone else selected for you. Maybe the help you need comes through a collection of mentors, a good therapist, and cultivating a meditation practice. You might need an executive coach, planned time with friends, and a pet rabbit.



Finding the help you need is part of your job as an entrepreneur, and learning to ask for it will bring you that much closer to authenticity.

Prioritize your needs

Figure out, right now, what you need the most help with on your entrepreneurial journey. Focus first on self-awareness to get an inventory of your strengths and weaknesses. Think about your most significant pain point and highest priority. Now you know where you need the most help. This is usually a relatively simple exercise, and it makes sense to do this often, as your answers will certainly change over time.

Find mentors who are relevant to your needs

Silicon Valley legend Bill Campbell or “Coach Bill” made me a firm believer in not just having one mentor, but multiple mentors. You need someone who can help you with where you are at your current stage, and as your company grows, you will need a mentor familiar with that level of operation.

You need someone who can help you think about what functional areas you’re not good at, and someone who can help productively frame your role as CEO. When looking for a mentor, be conscious of accessibility and relatability. Often people looking for a mentor will seek out someone who is ridiculously busy or someone who ran a company 20 years ago and doesn’t understand what’s happening in the industry now. It’s most important to find people who can relate directly to what you’re doing at the moment. 

Join a group

Early in my journey, I was invited to join the local chapter of the Young Presidents’ Association (YPO), which is like a support group of and for CEOs. Joining YPO had a massive impact on my career by helping me hone my job skills through sharing experiences and learning from other CEOs and entrepreneurs.

YPO is one of several global organizations designed to help founders and CEOs. Others include Entrepreneurs Organization (EO), Vistage and Chief Executive Network. No one ever perfects the craft of being an entrepreneur, and having access to people who understand the challenges you may be facing at every stage is a fantastic resource. The key is to find a group that works for you and provides you with opportunities to expand your perspective.

If there isn’t a chapter of YPO near you, or it’s not quite the right fit, consider organizations like your local Rotary Club, small business association or Chamber of Commerce. The key is to search for organizations in your specific field of business, online or locally. If the right group for you isn’t out there, consider starting one yourself.


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Get a professional coach

For the longest time, I couldn’t imagine why a founder or CEO would need a coach. It seemed like a sign of weakness. Boy, was I wrong. Inspired by Coach Bill, I found an executive coach who taught me how to be good at my job. I believe Coach’s exact words were, “Steve Jobs needs a coach. Tiger Woods needs a coach. No offense, but why the hell doesn’t Mike Smerklo have that kind of help?”

Get a dog

OK, maybe you don’t have to get a dog specifically, but you do need a support network outside of work to give you the love and care you need to do your job and navigate all of the ups and downs that are coming your way. Help doesn’t always have to be advice or mentorship. Sometimes it’s nice just to have someone who loves you unconditionally, warts and all.

“Mr. Monkey and Me: A Real Survival Guide for Entrepreneurs” will be available on Nov. 17, 2020 wherever books are sold and can be purchased via StartupNation.com.

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