Why I never get it right the first time (and never will)

The last few weeks, I’ve been repeating something to myself and to anyone who will listen to me pontificate about my experiences as a new entrepreneur – “Shit never works out the way you want it to. You have to keep trying new things”

It’s been a huge learning for me. What no one tells you about starting your own business or doing freelance, you never have it figured it out. Rarely ever. But definitely not the first time.

I’ve changed my website, my services, my packages, and my prices probably over 1,000 times since I came up with the idea for my business in August of 2018. The only thing that’s stayed completely consistent is the name - Tall Hair Creative.

Even now, I’m still constantly changing things up. Whether it’s swapping out the freebie I offer or making the workbook I was previously charging $10 for, into the freebie.

That’s just the nature of the business/entrepreneurship/self-employment. And it was only until speaking with other business owners that I realized that not getting it right the first time is the rule, not the exception. And most of the time it takes a second time, a third, or even a dozen more times to see some success. It’s just the facts. The universe has deemed it so. Doesn’t mean that I/you will never find success. It just means you can’t quit. You have to keep trying.

There was a time when this would have made me a nervous wreck. In my post-college career, I was obsessed with creating the perfect project plan at work. I would gather everyone’s input. Make sure all parties agreed to their work and timelines. And I was sure that all of our responsibilities aligned with the project goal. The project plan was my way of ensuring that we could execute this project seamlessly. Spoiler alert: My project plans were followed to a T exactly 0% of the time. There were always problems. Everyone involved would be shocked and stressed that we were encountering issues. Office drama would ensue and everyone would be passively aggressive to one another.

Until today at 1:15am, when I was brainstorming what I was going to write in my newsletter for you lovies, I believed that the failure to execute a project seamlessly was 90% due to my co-workers. (I could accept 10% of the blame. But that’s it. Because I made a project plan! Half kidding.)

I just had a huge epiphany, moments ago. Those project plans didn’t work out, not because of any one person’s incompetence, but because shit never works out the first time.

“Shit never works out the way you want it to. You have to keep trying new things.”

In my own experiences, at multiple workplaces, I had dozens of managers and colleagues give me negative feedback if the slightest thing went off. So, I was very anxious to avoid mistakes if I could. But it never worked out and I always felt like I was failing, making me into an anxiety monster with crazy project plans, always mad at colleagues. Due to all the rules, personalities, stakeholders, expectations, regulations, hierarchy, and norms, in a traditional office culture, it’s really hard to practice this concept. Workplaces force us into perfectionist thinking.

I wish that instead of all that negative feedback, someone would have just told me, “Shit never works out. You have to keep trying.”

Some organizations are adopting methodologies like Holacracy, Human Centered Design, and agile, all of which I am a fan of, and are all aimed at making teams more flexible. But it’s really hard to reverse perfectionist thinking, especially in a structured environment like a workplace. Unfortunately, you can’t just bring in a book or a workshop to change the way everyone’s been thinking for their entire lives. But that’s another newsletter topic J

As an entrepreneur, I had to learn to let go of perfectionist thinking. I had to accept the fact that I will invest my time and energy in areas where I will never see a payoff. And that’s okay. It just means that I have to keep trying new things.

So, I leave you with this – Don’t just accept that you’ll fail at some point. Fully embrace the fact shit never turns out how we think it will. We are always failing and changing. The sooner you accept that, the quicker you can get to being adaptive and creative – to really get shit done!

In the spirit of change and evolution, I’m also announcing four new products this week! Everything from photography - branding - website design. Continue reading to learn about each of them!



If you blog, or are on social media at all, you need new photos constantly. You can never have enough content. We’ve come up with a plan for you!

Our monthly subscription plan gives you 50% photoshoots.

A 30-minute photoshoot each month with 20 edited images. $49/month. 6-month commitment minimum.




This is a 6-month coaching/design program for the budding entrepreneur. We meet once a month for one-hour to dive into a specific topic - a mix of coaching for clarity and discussing the custom design products I’ve developed for you. By the end of the six months, you will be clear on your business plan, your brand identity, and how to launch.

$200 per month (plus 50% off any one photoshoot).



This package has all the foundational elements you need for your brand and website - a customized Brand Style Guide & website refresh! $500 (plus 50% off any one photoshoot).



Specifically designed for anyone making a significant portion of their sales online (services, digital, or products). In this package, I will design your Squarespace website and complete e shop!. Everything from your Homepage, About, Contact, AND your whole inventory & e shop.

$1,500 (plus 50% off any one photoshoot)


Questions about any of the above? Email me stephanie@tallhaircreative.com.