When will we stop doubting ourselves?

At 41, I thought I had life figured out. I have had an amazingly successful career in the nonprofit world, transitioned to a successful business owner and writer. I have completed college and graduate school twice. I read everything I can, take every class I can, devouring knowledge and new skills like they were candy. In my mind, I could say I was established and confident.

But was I? Recently I found myself in a situation I was not prepared for or able to really understand. I have a policy that I meet with clients to see if working together is a good fit. From there, I send a proposal, gather what I need to complete the job, and do the work. I hardly work at a client’s office, unless I need information or it is necessary. Working from my office is by far the most productive thing for me, and allows me to work around my family.

Yet somehow, no matter how much we know ourselves, no matter how well we know our policies, we also encounter people who somehow seem to push past them. I found myself in this exact place with a client. This was not the first time I had felt this way with this client, or the first time I had said as much to the client. Prior, they have always brushed it off, as if I was the issue as if my wanting to complete a job in a timely manner was an issue. This last time, I had had enough. I stood my ground, set the boundaries, and waited. And waited. No response, no email containing what I needed to complete the job. As I wavered on calling and apologizing, a friend told me that if I felt as though someone was taking advantage of me they were.

While I was so grateful to hear her words, to feel someone in my corner, I was furious that I needed to hear her words. Why did I need someone else to justify my feelings? Why was I not confident enough to stand my ground and say no? When will the moments of doubt, the little voices in my head stop? I fear they never will. As I watch other business owners, carelessly give confident answers, I wonder when I will be able to do the same. Is being confident something that some people are just that much better at than others?

Life has thrown me a lot of curveballs. I am in a place I never thought I would ever be in. I did not plan to be a business owner or writer. I honestly never really had a plan, I just always showed up, worked hard, and took advantage of every opportunity. I honestly don’t have a plan now. I know that if I work hard, keep showing up, success will happen. I have no other plan than that. Perhaps this is why I struggle with confidence, why I question myself and my decisions. Maybe if I was more focused, more certain about what I wanted, I would be more confident.

I have to say, I do wonder if the people I think of as confident really are that confident. Maybe they are as uncertain as I am.

Sincerely,

Sara O