I was planning on posting an interview today with my friend Mike who is a fellow sidepreneur, but I just went through an experience that I felt would make for a helpful and valuable blog post on Sidepreneurial. I don’t think this will be a long blog post, but the message behind it is very powerful.

You have to have confidence in yourself.

You have to. If you don’t, it will poison your efforts to create a successful side business. It will be hard to get clients. You’ll be doubting everything you do. And ultimately you’ll fizzle out. I think it’s natural to doubt yourself sometimes because, after all, we’re all human. But you can’t let it get to the point where you have zero confidence.

How to build confidence.

In my own personal opinion, I think confidence comes from building experience and skill in your craft, believing in the services you are providing and making a conscious effort to keep improving the services you provide to clients. Experience, even just a little bit, goes a long way because it helps you when you have to talk to current and prospective clients. Also, when you believe in what you’re doing…and when you’re continuously upgrading your company’s services…I have found from experience that it builds confidence as well. This assumes of course that your clients are happy and they are seeing results. Results might not be immediate depending on what your side business is, but if you focus hard on serving your clients, and improving your services, results are pretty much inevitable in most cases, right?

The sales call that prompted this post.

I recently went on a sales call for my full-time job. The prospect was a very large insurance company, but going in, I didn’t fully understand how big they were. I was prepared of course in terms of what we could help them with, but I didn’t know they were a 1.5 billion dollar company. We were going in to talk about their digital marketing and possibly direct mail marketing. Being I’m in charge of the company’s digital marketing, I was going to be a big part of the meeting.

Well, we get to the building and it’s IMPRESSIVE. Big and beautiful. I’m thinking hmmm, ok. The CEO’s assistant comes out to get us and directs us to their conference room and WOW. The conference table was probably 30 feet long and the room itself was huge. It was at this point that I felt self-doubt creeping in like I was out of my element. I had never been in a conference room like that and it was starting to become clear to me that this was a very large company.

People from the company started pouring into the room, 8 in total from their marketing department. The initial atmosphere was kind of rigid and corporate. The CEO came in about 5 minutes later and we filled the time with small talk, mainly about our family business. Once the CEO came in, and everyone sat down, I became very aware of the voices in my head.

“What are you doing here?”

“This company is too big for your services”

“Are you sure you can do this?”


It’s funny because as I’m sitting there handing out my business card to everyone, I’m telling myself to stop doubting myself. I’m telling myself to have confidence. I’m telling myself to stop over thinking this situation. It’s just a conversation about marketing…yes the company is huge, but people are people.

What I ended up doing is calming myself down. I thought about the experience I have and the dozens of client projects I have worked on. I controlled my breathing. And when it was my turn to talk, I spoke with confidence and everything ended well.

What this taught me.

This experience taught me that confidence is crucial. If I didn’t have confidence, I would have gave into my thoughts and floundered in the meeting. Yes, it helped that I’ve had years of experience and many sales calls under my belt. But this was definitely the biggest meeting I’ve ever had where I was expected to play a big role…and the self-doubt was creeping in, fast. But I believe in myself, kept myself calm and focused on speaking in the meeting with confidence.

What I want you to walk away with here is you have to have confidence in yourself and in the services you are providing in your side business. It’s super important!

Focus on:

  • Building your skills;
  • Getting experience by offering your services for projects, big AND small;
  • Making a conscious effort to believing in yourself even when doubt creeps in;
  • And lastly, how can you keep making your service better and better for clients?

This won’t be an overnight thing, but if you focus on the 4 things above, I’m very certain that you’ll build confidence that will help you grow your business and get you through moments of self-doubt.