085 – Overcoming Entrepreneurial Insecurity

by | Mar 22, 2018 | Podcast

Have you ever felt unworthy? Does it seem like others around you are accomplishing more than you are?

In this episode of The New Music Industry Podcast, I explore entrepreneurial insecurity and how to re-frame your perspective.

Podcast Highlights:

  • 00:14 – You are where you are
  • 00:43 – Insecurities
  • 01:07 – Stop comparing
  • 01:56 – Taking risks
  • 02:20 – Reflect on the chances you’ve taken and where you could be
  • 03:53 – The importance of staying in the moment
  • 04:54 – Your journey is uniquely yours


Have you ever felt like you should be further along in your music or entrepreneurial career than you are?

Have people ever said to you something along the lines of, “why do I feel like you should be more recognized and better known than you are?”

On the one hand, it’s nice to know people think so highly of you. That can be a confidence booster. On the other hand, you might begin to feel discouraged, because you aren’t sure what you did wrong. You don’t know why you aren’t “further along” than you already are.

If these thoughts go unchecked, they can become a source of stress. You may start to feel depressed about your situation, because you wish you would have accomplished more by now.

Pretty soon, you’re looking at others who’ve achieved great things, and you begin to feel insecure about where you are. I know I’ve felt this way recently and know other entrepreneurs who’ve felt it too.

You may not feel as though what you’ve accomplished so far is significant. But that doesn’t mean it isn’t. It just means you’re comparing yourself to others.  So, I want to encourage you to…

Stop Comparing

I’ve written a post on the blog about comparison being the source of all unhappiness.

Take that any way you want, but ultimately, comparison is unhealthy, because your journey is your journey. It won’t be the same as anyone else’s, even if you model your life after your heroes.

Your journey is your journey and it won't be like anyone else's. Share on X

When we compare, we are rarely fair with ourselves. We end up comparing our blunders with someone else’s highlight reel. And, a highlight reel is just that – a collection of someone’s best moments. Rest assured, they’ve made some mistakes along the way too, perhaps bigger mistakes than you’ve ever made.

I know, there are plenty of people out there who’ve accomplished amazing things, and you want to be one of those people. But it wasn’t necessarily more intelligence, more smarts, or more talent that got them to where they are. Oftentimes, it’s just that they’ve figured out a few things you haven’t.

Hard work doesn’t guarantee success. But all things being equal, someone who takes more chances will likely have a better chance at success than someone who takes fewer, wouldn’t you agree? So, let me ask – are you taking enough risks?

I know it’s tempting to compare yourself to others and what they’ve accomplished, but I would encourage you to stop thinking that way. Instead, focus on what you can do today to make progress towards your goals and dreams.

Focus on what you can do today to make progress towards your goals and dreams. Share on X

You should also take some time to…

Reflect On The Chances You’ve Taken & Think About Where You Could Be

If you’ve been a musician or entrepreneur for any length of time, you’ve probably tried your hand at a lot of things. You deserve credit for what you’ve done, regardless of what the outcome was.

If no one has ever recognized you for things you think they should have, here I am extending recognition to you right now – good job.

And, that’s the way I’ve convinced myself to look at things as well.

If everything had gone according to plan, I would probably be a millionaire by now. Who knows where I would be or what I would be doing. Maybe I would still be adding value to the world through this podcast. Maybe I would have moved on to other projects.

What matters now isn’t where I could have been. All that matters, is my determination to keep going and to do something daily that causes me to love life.

I’ve experienced many hardships in life, as I’m sure you have, and some have made me want to give up, especially recent challenges. But I didn’t give up. I just kept finding ways of reinventing myself and my approach. I’m finding it necessary to adjust my approach yet again here in 2018.

The reason I say I could have been a millionaire by now is because I’ve reflected on the chances I’ve taken. I’ve had a long-lasting music career. I’ve started many businesses, websites, blogs, and YouTube channels. I’ve invested in businesses. I’ve published quite a bit of music, many eBooks and courses, and even a full-length book. I have a second book on the way. I’ve been involved in several community projects too.

Even with all that, I have yet to break six-figures in a single year. But you know what? That doesn’t bug me. I am exactly where I need to be right now, learning the lessons I need to learn. I have a purpose to serve exactly where I am, even though I might lose sight of that fact at times.

There are things I want to achieve, people I want to meet, and places I want to go. But for whatever reason, where I am right now is an important part of my journey. And, if I don’t enjoy the journey, will I truly be fulfilled when I reach the destination? No.

As I see it, there’s no need to hurry. I’m not saying I want to prolong the journey, nor am I saying I want to take my time getting to where I want to go.

But there’s also no reason to delay gratification and enjoyment indefinitely. Tomorrow is not guaranteed. I’m not going to be extravagant with my spending, because I care about my future, but some opportunities won’t come around twice. It’s one of the reasons I went to Japan when I did last November.

Life isn’t all about work. So, I’m going to be deliberate about finding something that makes me happy today. But I’m not going to apologize for being driven either. I’m going to keep pushing forward, because I believe in myself and what I’m sharing with the world.

If you’re feeling insecure right now, remember that your journey is your journey. It’s uniquely you, and no one else will have the same experiences you have. That’s what makes it worth living. You will experience some hardships along the way, and they will send you reeling. But don’t give up – your dream is worth it.

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