5 Lessons I Learned After 5 Years in Business

I started ASMM Digital Marketing almost by accident.  I was unhappy in the job I was working but had not completed a resume in 26 years and the prospect was terrifying.  Instead, I started working with small businesses I knew I could help.  My thought was that I would work with these clients, start working on a resume and find a real job shortly after.  Five years later and I still don’t have a resume.  I do however have 5 employees, a brick-and-mortar office, and five years of lessons learned about entrepreneurship.

I am not an entrepreneur expert.  I am not someone who is going to tell you how to make your first million dollars your first year in business.  And more than anything, I am not the person who is going to sugarcoat the difficulties of owning a business.  But I do believe that after five years I have learned a few things that can help those of you who are considering dipping a toe in the entrepreneurial waters. I can offer five things I have learned after five years in business.

Trust Your Gut

Being a new business owner reminded me so much as being a new mom.  I was supposed to have all of the answers.  I was in charge of a little human after all.  I read all the books, consumed all of the podcasts, and listened to every speaker I could find who spoke on being a parent but from the first day of motherhood, I realized there were some answers I just couldn’t find in a book.  There were some things I had to figure out on my own.

Being a business owner was very much the same way.  In my first year in business, I had an expert in my field tell me that I couldn’t scale my business.  That it was a “cute idea,” but it would be cost-prohibitive to scale it.  In my second year, I had another expert tell me that people weren’t going to buy what I was selling. In both instances, I had to trust my gut. I had to believe in what I created or walk away.

Your vision is not always clear to those around you.  It’s important that you understand what that vision really is and how important it is to you to stick with it.  Once you are clear on that, trust yourself first, and only if you start to really falter should you let other advice move you off course.

Every Interaction is a Networking Opportunity 

Before you walk away, hear me out.  I don’t mean that you should be hawking your wares to all of your friends and family every time you see them. I see networking as a means of building relationships.  The more relationships you build the more opportunities will come your way.  But again, hear me out. I am not suggesting that you build relationships with the end goal of building your business.  Instead, build real relationships.  Meet people, learn about them, and help them when you can.  Sometimes these relationships will turn into opportunities for them to refer you business.  More often than not they will turn into opportunities for you to help them build their business. 

But without a doubt, these relationships will benefit your life in some way.  As an entrepreneur, your life and your business are intertwined.  When you are happy outside of work you are happier inside of your business as well.  Being an entrepreneur can be lonely.  Following this tip, building relationships, creating a network, can help you feel less so.

You Are Not an Expert at Everything

The one entrepreneurial confession that shocks people most often is that for the first 8 months in my business I was constantly forgetting to bill people. You heard me right, I was working for free without meaning to.  Luckily, I realized this was a problem and I hired a bookkeeper who not only helped me invoice people but helped me set my new clients up with automatic payments.  Suddenly, I didn’t have to worry about whether I was getting paid or not.  With the automatic payments, I had more security and with my bookkeeper reporting to me monthly, I was able to pay attention to other areas of my business. 

My next hire was a part time employee, a personal assistant. I had finally calculated how much my time was worth and realized that if I was billing at $250 an hour, then spending an hour on the phone trying to get my dishwasher fixed was a little ridiculous.  When I hired my personal assistant, I was honest with her about this.  We talked about what I was doing for my clients, how much I was billing, and why having her on board was going to help me.  For the next three months, she constantly reminded me when I was doing something that was below my pay grade. 

Now, we do this for each of our employees.  How much is their time worth to the company? Why does this matter?  Well, when we first moved into our office space, we took turns vacuuming and dusting.  Then we realize that hiring a service to clean would actually save us money.  Understanding your expertise means understanding your value.  When you have that number, you are armed with the knowledge you need to scale your business.

Dump the Bullies

One of the hardest things to do as a business owner is to fire a client.  You see the money they bring in and you worry that letting go of that income will hurt your business.  But, without exception, we have found that clients who bully our staff are not worth the money.  We want our team to be happy.  We don’t want them walking out of work each day complaining about what happened there.  Even if they think you are the world’s best boss, eventually, they will associate that client’s behavior with your business and they will leave. 

There is a side benefit to dumping the bully.  Again, without exception, each time I have had to let a client go, we have experienced an upsurge in new business.  It’s like the universe is rewarding you for taking care of yourself and your team.  More likely, it is because that business was being ignored while you dealt with the bully.  Bullies take up your time and they cost you money.  Letting them go is almost guaranteed to be rewarded with a happier staff and more time to build your business.

Know Your Value

I think the hardest lesson I learned was understanding how much value we were bringing to our clients.  When I started my business, my pricing was so low that I had several clients sign contracts, then say, “Now that that is done and I am locked into that price, I need to tell you, your prices are too low.”  Each time I would raise it just a little and each time I would have someone tell me the same thing again. I have spoken to other business owners who have experienced the same thing.  Listen to your clients.  If they tell you your pricing is too low, then it’s time to increase it. 

Another good hint that it’s time to increase your rates is when clients are coming in so fast you can’t keep up with them.  This is especially true if you have competition.  If you are beating out the competition because of price, it’s probably time to raise your prices.

Take the time to consider your pricing carefully.  How much does a client actually cost you?  How much is your time or your staff’s time worth and how many hours are you spending on them?  Although you don’t always, or even most of the time, want to base your pricing on an hourly rate, understanding the value of your time is a key component of understanding whether you are charging your clients enough.


The idea behind sharing my entrepreneurial lessons was to give you one lesson for every year I have been in business.  But I would be remiss if I didn’t end with the simplest and most important lesson of all.  Take time to breathe.  This can be a few quiet moments before you start your day.  It could be the 15-minute cushion you put between meetings or it could be my favorite way to breathe, taking a few minutes between meetings, projects, or calls to step outside, walk around the block, feel the breeze on my face, and just clear my mind.  As an entrepreneur, you are juggling a lot of balls.  If you don’t take time to breathe, the balls will drop.  Without you, there is no business. Take care of yourself daily. Breathe.  The business will be there when you come back.

Article written by featured guest expert: Ann Brennan

Ann Brennan is the owner of ASMM Digital Marketing and the founder of Burgers and Bands for Suicide Prevention. Follow Ann on Twitter

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