My 3 Biggest Challenges In My 1st Year of Biz

My 1 year business anniversary is at the end of this month (I can’t remember the exact date, so that’s what we’re rolling with), and I’ve been thinking a lot about how to share about it and how to commemorate it.

I have had some big wins…

And I want to celebrate those…. but what I really want is to be real, raw, and honest with you about what it took to create those wins, and the pitfalls along the way. I know I truly have learned from others who have gone before me, and I want that opportunity to be available to all of you!

So I’m going to share my three biggest CHALLENGES I’ve experienced this year (in this business specifically – not my other) and how I’ve dealt with them, and how you can too.

CHALLENGE #1: Fear of Success

I’m starting with mindset because it’s such a crucial piece of overall success. My biggest mindset challenge this year? A fear of success.

I know, it sounds counterintuitive and some of you are probably thinking that you can’t relate… but read on because I know you will relate on some level because whether we’re afraid of success or afraid of failure it always comes down to these two things…

  1. What people will think of us
  2. What pressure will be put on us

I had fears around what people would think of me starting another new business, if they would think I was full of myself or out of touch with reality. I worried about the pressure of succeeding in business because I knew the weight of running an organization and another business. I worried about the new levels and new devils that come with success, and I let myself believe this was all a lot to handle.

I had a lot of negative experiences of success in my past… Like getting the “dream job” and realizing it wasn’t a dream, so my fear naturally gravitated toward success. For those who have a fear of failure it’s often similar… you’ve had negative experiences with failure in the past so your fear gravitates toward that.

However, what I’ve learned this year is that all of this is my own decision. My own story. When I spoke with conviction and certainty about my new business, 9 times our of 10 I didn’t get the bad reactions I was expecting, and if I did I cared less than I thought I would.

When I let myself feel pressured and overwhelmed and sat in that story… I felt serious pressure. When I pulled back and got support… it alleviated.

So my biggest mindset lesson this year is to not get stuck in old patterns. To not bring my 9-5 story into my entrepreneurial space. To recognize when that story was showing up, and to take action to change it. To realize this is an ongoing process and I will never be without fear, but that I can decide not to let it control me.

I’d love to challenge you to look at what stories you’ve been carrying around with you from past experiences that you’re bringing to your current business. Is it time to get support re-writing those? Is it time to take action and punch fear in the face?


CHALLENGE #2: Building a Team

This has been one of my biggest challenges (yet most transformational opportunities) as I’ve grown my business, and honestly? I’ve been a little embarrassed to admit it.

I would often think….I used to hire/fire for a very large team in my 9-5. I have my MBA with a concentration in leadership. I’ve had a ton of leadership training. I co-host a freaking podcast on leadership… WHY IS THIS SO CHALLENGING?!

And there was some shame/embarrassment to sharing it, but as soon as I did I realized that this is a challenge for MANY of us as we scale out of being a solopreneur in our businesses, and that I wasn’t alone.

As soon as I decided I was going to find the RIGHT fit, I was going to put in the work to make SURE it was right, and I was going to make sure they worked in their zone of genius so I could work in mine… I found AMAZING people to bring into my business.

It has been the most worthwhile thing I’ve dedicated my energy to as I’ve grown my business. So, if this is a challenge for you I implore you to keep going. Put in the work to build a team that you love and that loves you. Kiss a few frogs before you find your prince(ss)!

Now I don’t even remember how I ran my business without my OBM Megan Schopieray and my VA. I am so unbelievably grateful for them, and am so thankful to everyone who pushed me to keep going until I found my dream team.


CHALLENGE #3: Balancing Between Leaning In and Leaning Back

This is another one that’s hard to admit, mostly because it’s something I still struggle with, and that is… finding that sweet spot between working and being in the flow and taking time away when needed.

Some of you will remember that around the partnership I took some time to unplug and pull back because I had been feeling the pressure and the toll that even things that are really amazing and fun can take on you if you’re not careful.

This continues to be a challenge for me as I also have an autoimmune disease (Crohn’s) that I need to be diligent about managing.

Sometimes I’m awesome at it. I can practice self-care like a boss, I lean back, I take time off, and I put my health and myself first.

Other times, especially when I’m feeling REALLY inspired and excited about what I’m doing (which to be honest, is luckily most of the time) it can be harder to pull back. It can be harder to justify the down time.

So what do I do about it? I get support. I have people around me that can remind me to lean back (and I do that for my clients as well). I check-in when my body is getting pissed at me, and I try to listen to those around me that know my tendencies.

However, I fully admit that as a high-performer (and an INTJ) this was, is, and probably will continue to be an ongoing process for me. The thing that has made the difference though, is RECOGNIZING it and being willing to get support around it.

I truly believe the phrase that we “teach what we most need to learn” and this is certainly my example. Many of my high-performing clients will tell you that I ask about self-care, celebration, schedules, and down-time regularly. I have “Self-Love Sunday” in this group and in my heart I know this is one of the keys to success. Yet, it doesn’t mean I am perfect at it. It also doesn’t mean I’m unqualified to talk about it.

So I’d love to challenge you to look at what area you’re teaching that you also need to do some learning in. How can you get support around that to grow your business and create the success you want?


Those are MY biggest challenges in my first year of business.

Now I’d love to hear from you… what have been some of your biggest challenges in business this year? What have you learned from them or how did you overcome them?