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Want to Start a Business in Retirement? 5 Ways a Coach Can Help

By Hilary Henderson April 11, 2019 Managing Money

Are you thinking of starting a small business in retirement? Taking on a coach is a really good place to begin.

To Be Coached or Not to Be Coached?

As boomers we tend to be cynical about the idea of taking on a coach – we see them as therapists with all the attendant stigma. That couldn’t be further from the truth.

A coach will not delve into your childhood and help you find reasons as to why you are in this position now. A coach is not there to help you with psychological problems.

A coach is not going to do the work for you, same as an athletics coach doesn’t do any running or jumping; they stand on the sidelines and egg you on to achieve your best.

Here are 5 reasons why you would take on a coach:

Appropriate Goal-Setting

A coach is trained to help you set a SMARTI goal for yourself (Specific, Measurable, Achievable, Responsible, has a set Timeline, and is Inspirational).

So often we set vague goals for ourselves, and when we don’t achieve them, we move the goal-posts. If we still don’t succeed, we might abandon our goal altogether. Do you recognize this sequence?

A coach will not allow this to happen. They know how to help you set a goal that has specific parameters and is achievable, and then they will hold you accountable for achieving it.

Organizing Your Ideas

When you have a myriad of ideas churning around in your head, it might be difficult to look at them objectively. A coach will listen to your thoughts and help you order them, then guide you to take measured actions on your way to achieving your dreams.


I like to think of a coach as an ‘accountability buddy’. He/she is in a position to hold you accountable for achieving the action steps toward your goal.

When I am being coached, I know it’s important to have material to discuss in my next session, so I work through my planned actions to better prepare for the meet. Being accountable to someone else is a fabulous motivator.

The Thought-Factor

A couch is trained to ask powerful, searching questions that make you really think. These questions are thoughtfully selected to get you to look at things differently and can result in very creative, ‘out of the box’ thinking.

Cheering You On

When you have a coach, you practically have someone to hold your hand and at the same time push you from behind.

Starting a new business can be a very lonely endeavor, so it is wonderful to have someone who is beside you every step of the way, and who, at the same time, will not let you slack when it comes to achieving your end goal.

Some may say, “but my spouse can do that.” Remember, a spouse or a good friend will not be objective.

What I Learned So Far

I am a coach myself but have recently learned that I do not ask myself the searching questions, nor do I manage to keep myself on track. I really benefit from having an objective person on the sidelines, encouraging me in my small business.

The power of taking on a coach lies first in paying someone to help you and to whom you are accountable. The simple monetary transaction ensures you commit yourself fully to the process.

The second powerful aspect is the ability of the coach to ask the searching questions, and to rise up above the everyday issues to see the bigger picture and, in that way, guide you to plot your way forward to see what is possible.

Who holds you accountable in your business? Is there a person whom you trust to brainstorm with? Would you like somebody to extend your thinking? Are you tired of procrastinating? Are you ready to commit to coaching? Let’s hear your thoughts in the comments below.

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The Author

Hilary Henderson is a Retirement Coach She brings to her coaching her experience as an Occupational Therapist as well as an entrepreneur. Her mission is to help people find relevance, purpose and meaning in their retirement years. Facebook is one way to reach out to her.

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