Connection and Confidence: One Thing is Like the Other

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Making a Connection Means You Can’t be Timid

I was a terrified child. I started the first grade at age 5, so shy that I wouldn’t speak to other adults. And the idea of going to school with children I didn’t know was frightening. For the first six weeks of school, I reported to the principal’s office every day. My exasperated first grade teacher didn’t know what else to do about my daily complaints of homesickness and nausea.

My timidity continued through elementary and middle school and on into high school. By my teenage years, I took comfort in finding a small group and sticking with them, rather than venturing into unknown friend territory.

Then in college, it all changed. I left the all-girl schools of my youth and ventured to the big state co-ed university. Suddenly, I didn’t feel scrutinized and was more comfortable being me.

I replaced shyness with curiosity. And my world expanded.

Until college, I didn’t see the value of being a connector. And because I didn’t value extending myself, I didn’t meet new people and my world was limited by the very boundaries I created.

What Does it Look Like Not to be Timid?

There are many definitions of timid. My favorite is apprehensive. When we are fearful about an outcome, our wariness may stop us from taking action.

Here are examples of the opposite of apprehensive or timid:

  • Speaking to a stranger before they speak to you – I like talking to people and enjoy striking up a conversation. You’ll know if the other person doesn’t want to talk and you can respect that. But when they are interested, the sky’s the limit as to where the conversation will lead.

Example: A month ago, a woman was seated next to me at the nail salon. I began talking to her which led to a pleasant conversation and an exchange of contact information. She texted a few days later and we made plans. Following a lunch get together, she invited me to an event she and her husband were having at their home on Memorial Day. I attended and had a delightful time. We now plan to get together again soon.

  • Making contact for advice – I feel fortunate when I get to know experts in a variety of fields. I have found they appreciate when I reach out for advice. More often than not, the wisdom they share is invaluable.

Example: I am working on a book and needed an objective reaction to a marketing plan. I sought out a friend who had headed up marketing for a nonprofit in New York City. Not only did he give me sound advice, he offered to connect me to a colleague who would have an additional important perspective. My friend followed through and I met a new contact who has also become a good friend.

  • Serving as a job reference for an acquaintance – I never take the request to serve as a job reference lightly. It takes time and effort. We must be thoughtful with our comments and willing to extend ourselves on behalf of the job seeker.

 Example: An acquaintance reached out to me to say she was frustrated about transitioning from for-profit to nonprofit work. I thought about who I could introduce her to, and then sent an email to several people on her behalf. Once she applied for positions in the nonprofit field, I agreed to serve as a reference. It was my pleasure to be of help, not only to her, but also to employers who were better off for meeting my acquaintance and considering her for their workplaces.

Three Steps to Improve Your Confidence

 There are three easy ways to boost your confidence.

  • Ask three friends to give you three reasons you deserve to be confident. Then add one of your own for ten reasons that qualify you to be confident.
  • Set three “build your confidence” goals for yourself. They could include meeting more people, taking a workshop, or trying a new skill. Then measure your success.
  • Write your three most important accomplishments and post them where you will see them. Now take each of the three accomplishments and learn to talk about them.


Becoming confident is the first and most crucial step to being a connector. Confident connectors know they have something to offer. Write me at and tell me why you are confident!


  • Ann Louden

    A seasoned executive in the nonprofit world, Ann Louden is the founder and CEO of Ann Louden Strategy and Consulting. Recognized for her expertise in fund raising, high profile special events, and campaign planning, Ann provides counsel to chief executives, staff, and volunteer leadership. Ann’s primary interest areas are education, health care for women and children, the arts, and adoption. As a cancer survivor, she led and was the twelve-year spokesperson for a breast cancer advocacy initiative that engaged thousands of survivors, volunteers and medical providers. With a mantra of bringing big ideas to life, Ann focuses on identifying a compelling vision and creating a goals-oriented plan for execution. An in-demand national speaker for the Council for Advancement and Support of Education, Ann is the recipient of the Steuben Excellence in Teaching Award and has been named as a CASE Laureate. She is the author of the upcoming book: From Social Courage to Connection: Lessons from Leaders Who Change and Save Lives. You can find her at

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