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Why It’s Lonely at the Top-and What Entrepreneurs Can Do About It

By

Angela Totman & Sharon Lechter

  |   November 6, 2026

  |   Categories: Leadership, Mindset

You find yourself at your desk, as CEO of your own business, surrounded by wonderful and enthusiastic employees…all looking to you for direction and the “right” answers.  You should feel great…right?

But instead, you have come face to face with the silent enemy of an entrepreneur… loneliness and self-doubt.

You have heard the expression “it is lonely at the top”.

What is worse is what that loneliness creates: an environment of fear and self-doubt that can become an entrepreneur’s greatest downfall.

What entrepreneurs leave behind

Prior to starting your entrepreneurial journey, you may have regularly met with your team or co-workers or had colleagues with which to brainstorm and discuss ideas.

Very likely, you were working with peers who had respect for you and your contributions to the company.  Your very identity may have been based on the position you held and the influence of that position.

Your vision of being in control of your own future was so exciting that you didn’t even think twice about the possibility of experiencing a lack of self-confidence.

You are familiar with the common pitfalls of entrepreneurship.

  • Having insufficient capital to get the business up and running (let alone profitable),
  • Accepting the financial risk of a potential failure,
  • Thinking too small
  • Creating a job for yourself instead of building a business

You are proud that you have carefully planned your new venture so as to avoid those pitfalls.

Your passion and adrenaline drive you forward with great excitement and your business is launched with great reception. Sales start flowing in, business is great, but something is not quite right.

When isolation becomes a business risk

You have made the decision to become your own boss but in doing so it meant walking away from the environment where you are respected by and enjoy the camaraderie of your peers.

Your identity, both personally and professionally, is no longer tied to your former title.

If your prior company was an active contributor in the community but your new company cannot contribute at the same level while it is in its growing phase, you may find that your influence in your community has suffered as well.

When you’re the one with the final say, the honest feedback that once came naturally in the boardroom or meeting room quietly disappears.

Your team respects you, so they hesitate to challenge you. Without a trusted peer to say, “I’m not sure that’s right,” every decision lands on your shoulders alone.

You begin to second-guess choices you’d once have made in minutes, and the sheer volume of decisions you’re making wears you down. Over time, the cost is more than emotional. It affects the quality of your leadership.

So how can you avoid this silent enemy? Or overcome it if you are currently experiencing this loneliness and self-doubt?

Five ways to build your entrepreneurial support system

Consider the following steps to streamline your transition into a respected entrepreneur with great industry and community influence.

  1. Get involved in one or more professional networking groups and consider becoming an officer in one of them. This will allow you to offset your former prestigious title with a position of contribution and influence.
  2. Form a Mastermind of Peers to support you in the creation and strategic planning of your business. Then set regular on-going meetings (complete with agendas) where you can connect and brainstorm with your peers in your industry as well as other entrepreneurs. Their advice and wisdom can help you navigate any obstacles that may come into your path and turn them into opportunities.
  3. Find a mentor who has experienced success in your field. Schedule regular meetings with your mentor.
  4. Offer to share your expertise and wisdom by serving as a mentor or member of a mastermind for another an up and coming entrepreneur.
  5. Build your team within your business with people you trust to provide honest feedback supported by business goals

Independence doesn’t require isolation

The silent enemy only wins when you face it alone.

Picture that desk again. You, the CEO, with the same enthusiastic team. But this time there’s a mastermind on your calendar, a mentor on speed dial, and peers who will tell you the truth.

The decisions are still yours to make, but you no longer feel like you make them alone. That’s the difference between leading in isolation and leading with support.

You don’t have to wait for loneliness to find you. This week, take one step: join a new networking group, reach out to a potential mentor, or start building your mastermind. It’s much more fun at the top when you have others to share the journey and the success.