My first six months as an entrepreneur (what I have learned) - By David Pride

Hard to believe that it has already been six months since I left my full-time job to pursue my goals and aspirations as an entrepreneur and keynote speaker. A lot has happened these past months and I have learned a ton. Below are a few of the biggest lessons I have learned in my first six months as an entrepreneur.

An empty calendar will fill itself, but not with things that matter. My first three months of self-employedness were pretty epic. The phone would ring, it would be my buddy Mike, Kevin, or Dean - they want to golf, boat or lunch. I would look at my calendar see that the afternoon was open and soon was on my way to enjoying a beautiful summer day in Maine. It felt great. Many times I would think I can't believe being self-employed is this...easy. Things that were meant to get done that day could easily be moved to the next day and heck, I had no boss so what's the rush anyhow? In many cases there were no major losses because of my 4.5 hour work day but, after a couple weeks of messing around I would find myself in crunch time at the end of the month when I was looking at my goals compared to my progress.

What I learned was that I need to schedule my day in detail. One evening while having dinner with Internet master Ross Lasley and his beautiful family, he shared with me how he does it. Ross schedules his entire day out, in detail - literally, hour-by-hour. He told me it helps him keep on track. I figured if someone as successful and intelligent as Ross schedules his day with discipline, I probably should too. I still can't schedule my day by hour but what I do instead is make a very easy to use To Do list using "Remember the Milk." a great ios application and browser plug-in. It helps me make a really easy to follow To Do list and syncs easily with my phone.

The next lesson I have learned during the past six months is, don't listen to every one. Now, I am not advocating you be a prick. I am simply saying that you started your business because you have an expertise in a certain area (hopefully). There are times when you are talking with people who do not have an expertise in your area that will tell you what you need to do next. These people mean well, but many times don't have a clue. Listen to their opinion, remember it's an opinion, and let it marinate. Trust your gut and realize that you will make mistakes but sometimes you need to in order to grow.

While we are on the subject of opinions, I highly suggest you hire a good bookkeeper, lawyer and accountant. There are many, many things that I am terrible at that involve numbers. Because of this I knew without a doubt I needed to hire a bookkeeper and an accountant. They do not work for me full-time, but they are there when I need them. They help me navigate tough situations and make decisions that make long-term sense for my business. I had many people tell me, "Just do that stuff yourself and save the cash." Those people were right...doing it myself would have saved me the immediate cash but cost me the aggravation of doing it myself. 

Other things I have found useful to hire someone else to do for me include: Cleaning my home, sending cards, organizing contact information of important people I meet, researching potential leads, reminding me to do certain tasks, and handling all my website updates. I'm an entrepreneur now - why waste my time doing things that have nothing to do with providing for my family and/or reaching my goals?

Another valuable line item I have found valuable to schedule into my day is an hour of "letting the wind blow" as my Dad would say. The saying comes from a walk my Dad and I took about five months ago. I thought it would be therapeutic for my Dad and I to meet at Spring Point and walk out to the lighthouse. As we walked I began telling him all about my life and how amazing it was to be pursuing my dreams as an entrepreneur. After about 10 minutes of this my Dad stopped at a nearby bench, sat down, and said, "Let's just sit and let the wind blow for a little while." To me it was a lesson learned - shut up every once in a while and just let life be.

As an entrepreneur, I have also found it very important to travel to cities larger than where I live. It is really easy to compare yourself to your peers and feel pretty good about your growth rate if you don't continue to stretch yourself. I visit New York City every three months. In the past six months I have traveled to: Orlando, New York City, Phoenix and Boston. Being someplace larger than where I live helps challenge my thinking and makes me set larger goals.

Become a voracious reader, listener, thinker and doer. I have had the good fortune of interviewing and hanging out with some incredible people. Do you want to know the one thing they all have in common? They all read about ways to improve their business and themselves. Seeing that one common trait was enough to convince me to start reading immediately. I also listen to a handful of podcasts having to do with my industry or just stuff that inspires me. A few of my favorite podcasts include: StartUp, Daily Boost, Dan Millers' 48 Days to the Work You Love and Tech411.

The final lesson I would like to share about my first six months as an entrepreneur is the realization that life is pretty stinkin' great when you run the show. There is no greater feeling than knowing that if I want a raise this month then all I need to do is work harder and pitch more clients. If we do a good job those clients will refer us to more potential clients and the beat rolls on.

“Twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.”

- Mark Twain