Biggest Mistakes I’ve Made in 20 Years of Business

You know the old saying that mistakes are why they put erasers on the end of pencils? Well, that might do the trick when you’re in the 6th grade, but when you’re a small business owner, mistakes have slightly higher stakes!

As a small business owner, I’ve faced countless difficulties throughout my career. Heck, like everyone else in the world in 2020, I’ve faced incredible challenges over the last few months! The good thing is that I’ve learned how to take those mistakes and learn from them. But trust me, that wasn’t easy! 

I’ve always found that the next best thing to learning from your own mistakes is learning from someone else’s! So, I thought that I would share some of the biggest mistakes I’ve made in my 20 years of running Jennie Lyon Digital Marketing and Virtual Assistant Services. Thankfully, every one of these stories has a happy ending, but I’m not going to lie, at the time, it was super hard. But hey, revisiting them will also remind me of the lessons I learned, so let’s go for it! 

Didn’t Hire My Own Virtual Assistant

Ok, here is the point where you all point and laugh at Jennie. In the first handful of years in my business, despite being a virtual assistant… I was super reluctant to hire one myself. In fact, I put it off for years.

I know, it’s hypocrisy at its finest! After all that I preach about the benefits of hiring a virtual assistant, I couldn’t take my own advice. And that led me to one of the biggest mistakes of my career. 

I’ve always been a workaholic, and becoming a small business owner didn’t help with that. Now that everything was on my shoulders, I started spending 16-hour days working to make my business a massive success. I put off necessary breaks, weekends, and holidays to spend every minute I could on my business. I didn’t take a vacation for the first five years! Moreover, I believed I could do everything myself. I mean, why bother hiring a virtual assistant when I AM a virtual assistant? 

For the first few years, this insane schedule seemed manageable. I was bringing in more and more clients, so why change anything? 

My first big wake-up call happened on a Friday night back when my son Eben was much younger. My husband Jayson and I had planned to take him to dinner and a movie. I was working that day, but the film was at 9 PM. No problem, right? 

My Ah-Ha Moment

At 8 PM, Jayson came into my office to ask if I was ready to leave. I was still at my desk and had a massive project in front of me that I NEEDED to finish. I was so swamped that I felt I couldn’t leave. It was awful. I ended up canceling on them, so they understandably went without me. Terrible doesn’t even begin to explain how I felt. I remember crying a tiny bit! I not only let down my family, but I also deprived myself of their company. And I love my family more than anything in the entire world.

That weekend, I decided that I needed help (possibly in more ways than one! :P). My current workload simply wasn’t sustainable anymore, at least not without sacrificing precious hours with my family. So, I made a choice. And that following week I hired… a virtual assistant.

Instantly, everything changed. Little tasks that took up hours of my day suddenly vanished. Hiring a virtual assistant was one of the best decisions I’ve ever made. Nowadays, I am off work every Friday by 5 to spend time with my guys (and my girls, the dogs)! I can take the weekends off to live my life, rather than bury myself in work. 

And here is the punchline: after I hired a virtual assistant, my bottom line actually improved, like a lot – double that year! I was no longer overwhelmed by everything, meaning that I could do higher-level work for my clients much faster. The joke, of course, is that I already knew all of this would happen. After all, it happens every single time one of my clients hires me. 

Sometimes, you really do need to hit rock bottom, huh? 

Growing My Team

This mistake also falls under the category of “Trying to Do Everything Myself.” Are you detecting a theme here? I may be a bit of a control freak! 

Despite making the massive step of hiring a virtual assistant, I was still somewhat overwhelmed by my workload. I pride myself on being a Jill of All Trades, offering my clients a multitude of different services. But eventually, I needed to realize that I can’t handle every part of a massive project myself.

To be honest, the instinct to do everything is something I still fight with today. Here is a recent example: In late 2019, I had an idea for a webinar for my own business. Now, if you listened to my episode on webinars, you know how much work goes into them. You need to write the script, create the slides, design and write the landing and thank you pages, write email sequences, create social media ads, integrate everything (so all of the pieces talk to each other!) and run tech support for the entire presentation. And I was handling every single one of these steps myself.

Don’t Put Your Business on the Backburner

Because the webinar was a personal project, I kept putting it on the back burner while focusing on my clients’ needs. Cobbler’s shoes, right!? After a full year, the webinar still wasn’t finished. While I knew I could do every part of the webinar, other people could do them just as well. Someone who was a full-time copywriter, a graphic artist, a web designer… In other words, I needed a team of experts.

So, I hired them. And you want to know what? Once I asked for help, the webinar came together faster than I can believe. I’m almost ready to launch, and plan to do so in November. (Stay tuned about that, I’ll give you a heads up when it’s ready!)

My big mistake here was presuming that I had to be the expert in every area. And while I CAN do it all myself, there is no reason why I should, especially now that I have a talented team behind me! 

Put Off My Health

Ok, to be fair, this is a problem that a LOT of small business owners struggle with every day. But in my case, it’s about more than just fitness.

Something that I’ve always known about myself is that I need to exercise every single day. While, yes, I need to keep in shape, it’s the psychological effects that are the most important to me. Building and running a small business is super stressful, and over the last 20 years, I started building some anxiety issues. But if you haven’t guessed from my other stories, I’m REALLY good at burying things and plowing ahead to do everything! If I have a massive project coming up for one of my clients, I buckle down, push the anxiety aside, and do whatever I need to get it done.

Eventually, I learned that the best way to handle my anxiety was through exercise. For years, I always started my mornings with a combination of weight-training and aerobics at home. It seemed that my body and mind responded well to this kind of exercise… And then suddenly, all that changed. I badly injured my knee. I couldn’t even bend it, let alone exercise on it. But I kept trying, ending up in a vicious cycle. I would hurt my knee, take a few weeks off to heal, hurt my knee again, and so on.

I knew that I needed to try something else, but I was afraid. After all, this was the key to handling my anxiety. So, I did what any reasonable person would do. I threw myself into my business and tried to ignore the problem. And unfortunately, I couldn’t hire a virtual assistant to do my exercise for me! Dang, now that would be amazing! 

I Discovered Yoga

Without my exercising habit, I soon found myself dealing with insomnia, stress, panic attacks, and aches and pains. It simply wasn’t sustainable. Thankfully, my husband Jayson came to the rescue (as he so often does). On one particularly stressful Saturday morning, he suggested that I go to yoga. Huh. Interesting.

I went into a studio and started a week-long free membership. Almost instantly, I felt better. My insomnia vanished. And my stress would melt away every morning. On top of all that, my knee got better! I’m not exaggerating when I say that yoga saved my life. 

Quitting daily exercise was one of the worst mistakes I’ve ever made, and I almost paid an incredible price for it. Thankfully, I found another type of exercise that gave me all of the same benefits of weight-training and aerobics, but with none of the drawbacks. You can learn more about my love affair with yoga here!

Now, I’m not suggesting that you go out, buy a yoga membership, and take a 6 AM class every morning (although it certainly worked for me). But taking the time to exercise every day can change everything. It doesn’t need to be a significant commitment. For example, some morning I jump on the elliptical and watch Netflix! Just pop in some headphones and go for a brief walk. Trust me, it will be worth the time! 

So, What Did We Learn?

Although, to be honest, this section is more like “What did I learn!” But hopefully, hearing about my struggles helped you with yours:

  1. Take the necessary time off. You deserve it, your family deserves it! 
  2. Hire someone to take work off your plate (A virtual assistant perhaps)
  3. Always put your family and health first (at least try to balance it as well as you can)
  4. A virtual assistant can improve your bottom line. 
  5. You can’t be the best at everything. You can try – but it’s hard to sustain.
  6. Hire a team of experts – hey I know someone who can help you with that! Wink, wink. 
  7. Learn what your body and mind need to stay fit.
  8. Find an exercise routine that works for you and stick with it.

The common theme in all of these stories is stress. Like I said, small business owners deal with a TON of stress. It comes with the territory. The trick to being a successful small business owner is to learn ways to mitigate and eliminate that stress. 

That could take the form of hiring a virtual assistant to take care of time-consuming tasks, bringing on experts to help with specific parts of your business, or taking the time to exercise daily. Every situation is different, but in my experience, these strategies WORK.

Free Download: How to Use Our Digital Marketing Team to Grow Your Business & Get Your Life Back

If you want an excellent overview of what working with a virtual assistant looks like, I’ve written a free workbook: How to Use a Virtual Team to Grow your Business and Get Your Life Back. Or, if you want to cut right to the chase, you could always contact me today for a free consultation! Let’s chat, small business owner to small business owner, and let’s figure out some effective ways to eliminate the stress in your life and business! Believe me, it would be a pleasure to help!

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About Jennie Lyon

Jennie Lyon is the founder of Jennie Lyon Virtual Assistant Services. Jennie specializes in helping busy entrepreneurs organize, manage, develop and promote their brand! She is devoted to helping small business owners and entrepreneurs with social media, content creation, email marketing, client relations, website management, and administration services. If you are a small business owner, coach or self-employed entrepreneur struggling to find enough time in your day to focus on what you really love - schedule a free 15 minute consultation with Jennie.

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