5 Essential Lessons Learned in My First 5 Years of Entrepreneurship

April 2025 marks five years since I made Anchor Watch Marketing official. That feels so wild to say. When I left my corporate job without a real plan for the future, I truly had no clue how much was coming my way. The last five years have held so much - Covid shutdowns, my wedding, becoming an aunt, health challenges - but AWM has been a constant in my life throughout it all. And the lessons I've learned along the way have been one of the greatest benefits.

Here are my 5 biggest lessons from my first 5 years of entrepreneurship.

Nobody actually has it all figured out

This one hits hard, especially in the age of social media. We've become trained to believe that everyone else knows exactly what they're doing and is thriving in all aspects of their lives and businesses. But the truth of the matter is, that couldn't be farther from the truth.

I can often be heard saying, "None of us started a business because we thought running a business would be fun. We started a business because we were passionate about what that business offers." Accepting that I couldn't be expected to be great at everything, normalizing the reality of the tougher times, and realizing everyone else was in the same boat - despite the highlight reels on social media - allowed me to give myself more grace and embrace not only help but growth.

If you truly want to find yourself in your business, go help someone else

I imagine this one applies to us service-based businesses more than others. But whenever I have felt overwhelmed or unsure where I wanted to take my business, I gained an absurd amount of clarity from helping others.

Whether it is through volunteering, mentoring, donating, or sitting on a board, your heart will pull you to the things you're most passionate about. From there, you can see what rises to the surface: what you offer up of yourself the most is most likely the thing you love doing the most. I thought I liked marketing, as a broad industry. But what I really love is strategic marketing. Getting involved with nonprofits made that all the much clearer for me, and has really allowed me to grow my business around that passion.

Learning to say "no" as much as (if not more than) you say "yes" is critical

When I started out, I thought everyone was a potential client. I think we all do this. You say yes to everything and everyone and make plans to figure out how to make it work later. "Fake it til you make it." But somewhere along the way, I realized that was a grave mistake on my part. I once heard that every time you say yes to something you don't truly want, that you're saying no to something you do want. And it changed my life.

Not every client is meant to be my client, and I have taken to (nicely) declining people that I don't think I'm the best match for. This has opened me up to filling my schedule with clients I'm excited to work with. It also reduces feelings of competition and comparison with others, because I'm more accepting that some people are right together and some aren't.

"No" is a complete sentence, and a super powerful one at that!

Community makes all the difference

I really had no idea how isolating it could be to run a business. It sounds so idyllic to be your own boss and not have to answer to anyone else... until you want someone to help you make a difficult decision or you have a hard day and just want to vent. For this and so many other reasons, community is everything.

Making real, authentic, human connections with other people - both other entrepreneurs and potential clients - is so crucial to making your business a success AND keeping you sane! Even if some of those people are considered your competition. Who else is going to understand what you're feeling better than someone going through the same feelings?? Covid definitely helped drive this lesson home for me as well.

It's ok to change things

People change, technologies change, consumer behaviors change, economies change, communities change. Change is truly the only constant. At first, it was hard for me to accept shifts in my business. I was worried I would look flaky or inconsistent if I changed up my offerings or shifted my pricing. But you know what? I never had a client leave because I changed something, and anyone who didn't sign on because I DID change something, wasn't meant for me anyways.

Accepting that the way things started doesn't need to be how they continue to operate has been extremely empowering for me. Over the last year, I've dealt with numerous health issues, including two surgeries, an infection that required a hospital stay, and more. If I had refused to accept that my business needed to shift through this phase of my life, either AWM would be no more or I would be sicker than I was when I started. But I changed things up and delegated more and refocused the business on different things. And here we are today, thriving.

Overall, I'm really proud of myself, my team, and the community I've built around myself and Anchor Watch Marketing over the last 5 years. And I'm excited to take all of these lessons and a whole batch of new ones into the next 5 years!

Anchor Watch Marketing is a boutique marketing agency focused on helping small businesses and nonprofits reach new heights with holistic, strategic marketing that truly makes sense. We are an all-female team, offering branding, marketing strategy development and execution, web design, content marketing, SEO and SEM.

Learn more or book a free consult call at https://www.anchorwatchmarketing.com/