How to Avoid the Mistakes I Made as a Serial Entrepreneur

You've seen the light! You're finally doing it. You're finally going to work for yourself. No more letting a time clock tell you how to live. No more cranky boss. No more waking up at 6am -- unless that’s your thing, of course. No more commute to an office that requires a parka in July, 'cause the air conditioning is controlled by a menopausal receptionist.

That's what I thought, too -- the “freedom at last” feelings are awesome, yes. However, lots of freelancers jump into business without a clear picture of just how much dedication it takes. (You will be wearing all the hats.) As a serial entrepreneur, running a copywriting firm, holistic healing practice, a wellness business, and most recently, this online temple, I’ve learned a lot. And, I've decided it's time to let you all in on some secrets. Or mistakes I've made. You know... the same thing.

  • Avoid doing it all by yourself. Team Charissa is now a four person team! (WOOHOO!) I seriously don't know where I'd be without my support staff. For a long time, I thought I could do it all, be it all... and that it would be easier if I just did it. HA. The first day I had my assistant on the job, she freed up so much time for me that I spent the second half of the day outside in the park, taking pictures for a class I'm in. GET HELP! It doesn't make you any less of an entrepreneur, or less of a boss, or less of a badass. Just get help. It'll free you up to do what you are really good at.

  • Avoid working yourself to death. Avoid a haphazard schedule. If you're going to be working for yourself, keep your business hours from corporate. Sure, you don't have to get up at 5am to commute for 90 minutes-- but you need to have set work hours. If you don't, you'll end up working yourself to death, or you'll never get anything done. When the time is up, the time is up. Honor the boundaries. My hours are 9am-5pm, Monday through Friday, for a reason.

  • Avoid the idea of perfection before launching. If I have to be the one to break it to you that perfection cannot ever be attained as an entrepreneur, then I get a trophy. And you do too -- cause that's a hard truth to choke down. It will never be perfect enough. If you wait for perfection to launch, you'll never do it. So many times I've scrapped a blog post, or a photo, or a layout, because it just didn't fit right... when in reality, my readers would've loved it. Take a deep breath, get yourself a green smoothie, and press publish.

  • Avoid four thousand systems designed to "increase efficiency". GROSS. Buckle down, do the work (delegate what you can!), and have a few systems in place. My favorites can be found in our upcoming resources post. (Looking at you, ConvertKit and Harvest. These two systems automate everything.)

  • Avoid imagining you're not the boss when conflict shows up. You wanted to be the boss, so be the boss. You guys, I hate playing the boss card. There will inevitably be a time when conflict arises, whether over a contract, with a staff member, or with a service provider. You are smart enough to run a business. Be smart enough to own up to your part of the conflict, and strong enough to stand your ground. Leadership can be hard -- but make an effort to treat your staff amazingly well, and lead effectively. You are the boss. Don't act like one -- be one.

  • Avoid copy that is ineffective. Whether you choose a professional for copy, or do it yourself, you cannot afford to have bad copy on your site. The truth of the matter: whatever you say is engaging your customers to either shop with you... or shop with your competition. Bad copy equals bad business.


Want a 1-hour training on how to automate and delegate? Lucky for you I have one! And it's FREE in my resources library!