What if you could skip the first couple of years of business and jump straight to the successful era? Well I can't promise success but you can learn from my mistakes.

It may not come as a surprise that many entrepreneurs give up in less than a year. What happens when after a few years things are what you were shooting for doesn’t come to fruition? Chances are you skipped some steps or made some mistakes along the way.

I am spilling all the beans on the biggest business blunders The Creative Boss made during the first 3 years in business.

1. Not Having a Clear Direction

Yep, you read that right. When I launched The Creative Boss in 2015, I wasn’t really sure what I wanted to do. It was an outlet, a place to share some of my best tips since running creative businesses online is hard. I didn’t really know what I wanted. I thought that it was a general information site. I thought that I only want to create courses; I didn’t actually create any. Create the Ultimate Opt-In Offer launched in 2016. And somewhere along the way, I decided that I would start offering design services. But really didn’t have a clue about finding and booking clients. So aside from some free projects, I didn’t even book a paying client in 2015, 2016 or 2017.

All of this was because I didn’t really know where I wanted the business to go. I knew that I wanted to be successful. To generate some income. But I didn’t put any real thought into it. And after a few months of client work, I have decided that it doesn’t align with where I see The Creative Boss or my life in the next five years.

I plan on traveling full time with family and know that my business needs to run even if I don’t have access to the internet for weeks on end.

Yes, I am dreaming of a more passive income source from The Creative Boss.

The biggest business blunder you can make is not having a clear idea of where you want to go or what you want to do. Unfortunately, this is probably something that you will have to learn through trial and error but don’t let it stress you too much.

2. Always Learning

So because I didn’t have a clear vision for The Creative Boss I fell into this “I just need to learn one more thing” cycle. I kept purchasing courses, reading blogs and books, just absorbing information but I wasn’t actually implementing anything.

I’m not saying don’t keep learning, but at some point, you have to take action or you are just wasting time and money.

I am still struggling with this. For example, I really convinced myself that I needed to take the 90 Day Year program to make it successful in 2018. I have read The 12 Week Year, I know the basics of what would be taught in the program, I need to implement that before dropping 2k on another course (which I am still sure is totally worth it, just not when you don’t have 2k to invest in a course).


3. Trying all the Damn Tools

Okay, hear me out on this one. I still believe that every couple of months you need to evaluate your tools and systems and make sure you are getting the most out of your set up. But what you don’t need to do is to swap between 4 different email providers 6 times in a year. It is a giant waste of time and probably cash.

I started out with MailChimp, I was using the paid plan (before they made the free plan a bit better). It was working. I hacked together a system that integrates LeadPages. But basically I had a tiny email list, under a thousand, and was spending a lot more than I was bringing in and I knew that needed to change.

Enter MailerLite, this is way better than MailChimp. My open rates improved, my list kept growing. And it was free. I found a great plugin for my content upgrades, Easy Content Upgrades. But some things were just missing from MailerLite. I wanted to be able to better track my subscribers and market to them better as I was thinking of services and digital products were in the works.

So I went to the platform everyone seems to rave about, ConvertKit, I really do love ConvertKit. At first, I found it clunky compared to MailerLite and swapped back after a month. 

I was tired of struggling with MailerLite lacking the features I wanted, so I decided to give ConvertKit a second chance. Things were better since I spent some time learning the tool and even created a bunch of super helpful blog posts.

Enter my end-of-year systems audit. If you have read some recent income reports, you can see that I am spending a lot more than I am bringing in. And deep down I wanted ConvertKit to do more. I tried to set up an automation for a webinar and none of the emails fired. It was probably user error, but it was extremely complicated to set up and it just didn’t work the way I wanted.

So I went on a hunt. I thought about going back to MailerLite as they recently made some improvements and included the features that I had come to expect. But I wanted to check out some other options. After a while, I finally found the hidden gem. This was email provider was about $5 more than I initially started the year spending with MailChimp and a half of what I was spending with ConvertKit and it has the capability to set up the automation sequences that I had in my mind..

So in the final month of 2017, I wasted a shit ton of time moving everything I had pieced together over the years to a single platform, ActiveCampaign.

Now I am not saying that MailerLite or ConvertKit are not good. They both were. They both checked the boxes of my demands of my business and I still recommended to lots depending on what your marketing plan is or will be over the next couple of months.

But I have wasted more time than anyone should trying to get this squared away for The Creative Boss.

I have tried countless other tools along the way to see if they were worth it so here is the brief version of what is worth it.

Forms: Typeform (free plan)

Project Management: Trello (free is okay, I use Gold because you guys love the Editorial Calendar and new sign-ups has kept me in “gold status” for a while now)

Magical Automation: Zapier (free plan)

Booking: Calendly (I use the second tier option but debating cutting out the separate “calls” I offer since I am hoping to eliminate client work)

Social Media Scheduling: Buffer (Pro Plan)

4. Overloading My Schedule

So between having two toddlers, homeschooling my 8-year-old, running a baby boutique on Etsy and trying to get The Creative Boss off the ground, I was burnt out. I was exhausted. I was simply trying to do too much.

And because nothing was really working, my thought was to keep adding more stuff on my plate. I even started designing a site that would be a drop shipping store of planners and accessories. Yes, I was overwhelmed and started to launch a third business.

It wasn’t until late November that I finally accepted that something had to go in order for other things to grow.

I looked at my schedule, marked my priorities, kids and followed it by which business I was most passionate about. Spoiler alert: It’s The Creative Boss.

I dumped everything else off my plate. I didn’t throw it out, but the ideas are still there and I may revisit them at a later date.

But that wasn’t enough. I needed to do a serious evaluation of my time and how much I could dedicate to growing The Creative Boss. I knew that this would be primarily done in the evenings, early mornings and weekends. So a full-time gig wasn’t going to cut it.

I mapped out my goals for each month of the quarter and the tasks I needed in order to reach them. I jotted how much time every task would take, rounding up. And by the time I broke them down to the days, I would work on them I ended up with most weeks being under 30 hours. And a good chunk of the tasks were things I could do with interruptions and only needed an hour or two of quiet time every day to knock things out. 2017 wasn’t a great year for me business wise and I have accepted that but I have finally crafted a solid plan going forward with one goal in mind. Increasing visibility. I know that for The Creative Boss to grow my audience needs to grow and everything that will be done will be with that in mind. If it doesn’t directly result in increasing visibility, it will not be happening in 2018.

This system has done wonders for my business, so much in fact, that I bundled it as a product. Planning Power Hour Planning Power Hour. I put together the spreadsheets and Trello boards I used to design this insanely productive, time-saving, method of making money in the midst of madness because everyone deserves this kind of life. And because that wasn’t enough there are even videos to walk you through how to get the most out of this system.

Get the Planning Power Hour Pack and take back your time.

Sarah Crosley

Sarah Crosley

Founder of The Creative Boss

After years of trying to run an online business I have seen quite a few ups and a whole lot more downs. I spent hours every day researching how to make a go at some elusive, passive income. I felt like it was something that was just a myth, and then I figured out what the real meaning of passive income was: to work smarter, not harder. It’s not just sitting around watching the dollars pour into your bank account, but you can create products that will sell and still be sitting on the beach or at home in pajamas, and I want to share with you what worked for me. I don’t want you to spend years trying, failing, and throwing in the towel.

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