June 8, 2020 | Entrepreneur

Alone On An Island: Entrepreneur Coaching

It’s not uncommon for entrepreneurs to feel alone. There is no doubt that being an entrepreneur is exciting – you can forge your own path, turn on a dime when necessary and call your own shots and you can take great pride in having built a business that has success and employs others.  The upsides aside there are certain realities and responsibilities that can be overwhelming at times: making payroll any given week, generating leads, closing deals, meeting launch dates, hitting financial targets, paying loans, the list is seemingly endless.

The number of times that an entrepreneur confides in feeling overwhelmed and alone is rare, especially to those closest to them. An outside thinking partner can be incredibly beneficial. It’s no wonder that entrepreneur blogs have grown in popularity! These blogs are a great way for entrepreneurs to touch base with what others in similar positions are experiencing.

How Is It Lonely?

Perhaps you’re asking, “how is it lonely?” Take a moment and think about the time investment, the unwavering commitment made to the success of the business. It typically takes periods of head-down determination to make it work. Along the way, questions may arise, internal doubts, feeling deeply vulnerable, both personally and professionally. Who do you do turn to for guidance?

Loved Ones?

Some entrepreneurs struggle to turn to a loved one and share their fears and concerns by assuming that the loved one may be wondering and/or thinking:

  • “You spend too much time at work!”
  • “Why are you doing this career?”
  • “What about me/the kids/our friends?”
  • “I don’t see you as much as I would like, so why do you think it is okay to offload on me, I want connection?!”


This is a tough one for many entrepreneurs, let’s take for example that the next quarter’s targets aren’t going to be met and therefore making payroll may be difficult. How comfortable would you be sharing this with a senior employee? What are the chances that this person will feel safe in their job? Would they begin looking for a more stable position elsewhere?

Investor / Venture Capitalist / Angel Investor?

If we continue on the financial target example above, there is a good chance that the company investor will already know what is on the horizon. So how do you navigate? How do you initiate the conversation about the struggles? What could this mean to the business and ultimately the funding?

What Can Help?

Without having a thinking partner, it can be overwhelming. Cracks can begin to form if these are not seen and addressed the results can be catastrophic for the business. Partnering with a coach who is not “in the game” but considers the larger play at hand can be incredibly empowering. This also saves the above relationships. Having a thinking partner, someone to share with can allow the other alliances/relationships to be as they are intended – to serve their highest purposes.

Reach out, I’m here to help, to be that thinking partner. I offer a bespoke approach to serve the entrepreneur in front of me. To partner in your growth and your business.

Leave a Reply

Your email address will not be published. Required fields are marked *