Dear Prosper Women Entrepreneurs: “I feel so alone!”

This article is part of our Dear Prosper Women Entrepreneurs series, in which the St. Louis-based accelerator Prosper Women Entrepreneurs answers common questions from women entrepreneurs. Dear Prosper Women Entrepreneurs, I’ve been working on my business for a few years now, and I’m starting to get a lot of traction.  But I’ve realized that being…


A monthly Prosper Mastermind meeting. Photo courtesy of Prosper Women Entrepreneurs.

This article is part of our Dear Prosper Women Entrepreneurs series, in which the St. Louis-based accelerator Prosper Women Entrepreneurs answers common questions from women entrepreneurs.

Dear Prosper Women Entrepreneurs,
I’ve been working on my business for a few years now, and I’m starting to get a lot of traction.  But I’ve realized that being an entrepreneur is kind of lonely!  As a woman business owner, I often work on my business at odd hours – early morning, late at night – and usually by myself.  My family and friends are supportive, but I know they’re not always the best people to go to for advice, and I feel like I need some skills that they don’t have.  How can I get more advice, perspectives, and help?
Lonely Entrepreneur

Dear Lonely,

The best thing about being an entrepreneur? It’s all you! The worst thing? It’s all you!

Congratulations on your growing business, and for recognizing you need more support. Being in control of your own destiny as a business owner is wonderful, but it’s also challenging. You’re right that being on your own can get lonely. Solo entrepreneurs also run the risk of feeling isolated in other ways – missing out on the experiences, feedback and skills of working with others. We all need outside opinions to help us grow, and this goes double for entrepreneurs. Let’s face it, we can get in our heads a little!

It’s not surprising that you’re feeling this need as your business grows, and there is a solution. Cultivating a board of advisors can provide you with the outside perspective and counsel you’re craving. Advisors connect you with resources and help you gather information, which will lower your risk as you’re making important decisions. They help you broaden your perspective and lend an unbiased eye to what you’re facing (that’s tough for friends and family!)  An additional perk is the mental and even emotional support a board of advisors can offer. They’ve been there and done that when it comes to entrepreneurial challenges and will understand your journey in a way that your social circle might not be able to.

Good for you for recognizing that you need more resources! Entrepreneurs can get stuck in an “I can do it all” mentality. This is especially true for many women business owners, who tend to have smaller networks and lots of plates spinning. So now that you’ve realized you need a board of advisors, how do you build and manage one?

There are formal programs that offer advisory groups for entrepreneurs (organizations like Vistage, Entrepreneurs’ Organization, or Prosper Women Entrepreneurs’ own Mastermind Program).  But you can also cultivate your own board of advisors based on the type of support you are seeking. And if you realize that you must stretch your network a bit to find the experts you need, that’s never a bad thing.

Consider the following when building and managing your board of advisors:

  • Think about expertise. You should recruit and select advisors based on their skills and experience. To do this well, you must identify your weaknesses (gasp!) and know what you need. If you find you are confused about using technology to scale your business, look for someone who has that skill set specifically. If you’re struggling with manufacturing and distribution, seek out someone with that expertise. Early entrepreneurs might be tempted to accept help just because it is offered. Knowing what you need and targeting your search will allow you to bring the right people on board.
  • Ask around. The knowledge you need might not be in your immediate network. Don’t be afraid to ask around, an ideal advisor might be one connection away.  Reaching outside your own network has the important benefit of adding diversity to your board of advisors – seek counsel from people who don’t look like you, think like you, or have the same experiences that you do.
  • Set clear expectations. Think about what you’d like your advisors to bring to the table and let them know from the get-go. Be clear about how often you’ll meet, for how long and what you’ll discuss. Setting expectations early will help everyone feel useful and productive.
  • Build trust. The best advisors should challenge you. Yes, you’ll be sharing business information with them, so confidentiality is important. But you’ll also be asking them to speak into your business in a way that is not always be comfortable. They might offer negative feedback on a product you’ve fallen in love with. Or, they might push you to grow faster than you thought you could.
  • Solicit real feedback. How often have you heard “that sounds exciting, great job!” from a kind friend or family member regarding your business? Advisors are there to offer real feedback, even if it’s not always what you want to hear. Create a situation where all feedback is welcome, and don’t bristle or act defensively when your advisors offer it. After all, that’s what you asked them to do.
  • Maintain the relationship. Like any good relationship, proper maintenance is key! Make sure you’re meeting regularly, offering frequent updates, and showing gratitude for their help. Some advisors will be with you for a single challenge and some for much longer. Open communication is key for a fruitful relationship, and you are in charge of setting the tone.

A board of advisors can help you overcome obstacles, connect with resources, and scale your business. They can also offer a sounding board during tough times, normalize your experiences as an entrepreneur, and help you celebrate your hard-earned successes. And once you gather a team of advisors around you, you’ll no longer be a Lonely Entrepreneur!

Entrepreneurially Yours,

Prosper Women Entrepreneurs

Have a question for Prosper Women Entrepreneurs? Contact Silicon Prairie News, and your question may be featured in an upcoming story!

Prosper Women Entrepreneurs was created to address the entrepreneur gender gap in the St. Louis region. We are a group of business leaders, thinkers, doers, innovators and students who want to make sure that our community is well positioned in the new economy and, more specifically, that women entrepreneurs are a vital part of its future.

Prosper Women Entrepreneurs is comprised of two separate divisions: Prosper Institute, a non-profit organization focused on training and mentoring women in the entrepreneurial community, and Prosper Capital, a for-profit organization focused on increasing women entrepreneurs’ access to growth capital and the number of women investing in early stage capital markets.


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