14 Lessons I Learned In Biz in 14 YEARS!

Happy September! September marks the start of fall, the air gets crisp, the leaves start to fall and I get to celebrate 14 years being a business owner this year!


Fall holds a special place in my heart, September marks the month I started my business, I fell in love with my husband in the fall, and I seriously LOVE boots, sweaters, football and all things pumpkin spice, butternut squash, and apple cinnamon spiced. Throughout this month and my entire 14th year in business, you are going to see 14 themed posts from me!


I thought it would be appropriate to start the first of the 14 themed posts with the 14 lessons I learned in business in 14 years! If you are a new entrepreneur, contemplating becoming one or a seasoned in business one I want you to know YOU too can do it and any goal is possible if you put your mind to it!


1 – Start before you are ready. I wish I learned this earlier in my career. I know for me, I have hemmed and hawed over different things in business only to realize that it wasn’t that bad or actually easy once I went and did it!


2 – Keep it simple. When I first started my business, I would create all these overly complex options for people to buy and I learned the hard way people actually want it to be simple


3 – Know your worth. Another lesson I learned the hard way. After years of giving discounts I’ve realized that those people who are asking for a discount aren’t seeing value in what I am offering and that is completely fine with me, they simply aren’t my ideal client. It literally took me over a decade to figure this out but once I did my sales soared.


4 – Be willing to do the work. There are no get rich quick schemes when it comes to owning and running a business. Many “overnight successes” you hear about in business actually took years to become a success.


5 – Define your goals. Yup, write it down, shout it from the rooftop, share it with EVERYONE and make a plan to achieve it. When I first started in business I made the mistake of not clearly defining my goals around my business, my sales goals and my personal goals. Write them down, put them in a place you can see them and work on them DAILY.


6 – Create systems to make your life easier. For the first 7 or so years of my business, I never had an onboarding process and it was a nightmare. When I started to create systems and hone them that is when I took my business from 5 figures to 6 figures. So take the time to create systems that help make scaling easier. While it may seem like a lot of work up front it is completely worth it.


7 – Surround yourself with incredible people. I’ve realized that old saying, ‘you are the sum of the 5 people you are around.’ Well, this is true, so choose people who are further along than you in business, who are smarter than you, and who lift you up! This has been a game changer for me in recent years.


8 – Get super comfortable talking about money. YUP! I wish I learned this in my first year in business but it took a bit longer…like 8 years later. To be successful I have learned that have to be able to talk money, proposals, and unfortunately late payments. Once I got way more comfortable having these conversations the more successful I have become and the easier doing business is. Do the money mindset work.


9 – Get uber clear about your strengths. When I first started my business I did it all myself and I did that for a very long time. It stunted my business growth. I realized that I wanted to grow and to do so I couldn’t do everything myself. After doing some digging and taking a few personality/strengths tests, I’ve realized my strengths are strategic, achiever, competition, communications and activator (thank you strengths finder). Therefore my role at my company is strategy, rainmaking and front facing. While I still oversee operations, proposal writing etc. I realize that these activities aren’t moving the needle forward and my time would be better spent prospecting than sending out invoices. As my business grows, I will find someone to handle this role – for now my hubby handles it. I recommend getting VERY clear on your strengths to get your business to the next level. While you might not be able to hire a full team right away but know what your strengths are and what you will plan to outsource.


10 – Block time to work ON your business. The best advice I was given in recent years (thank you Sue B. Zimmerman) and it was a game changer for me. Once I started treating my business like my best client it changed how I saw and treated my own business. I started taking myself, my business and my marketing way more seriously. I began to feel an obligation to serve and give value to my people.


11 – Spend the time to define WHO you want to work with. This seems silly but when I took the time and did the work to define who I wanted to work with the universe conspired to surround me with dozens and dozens of these opportunities. Do the work and know with great specificity whom you want to work with.


12 – SAY NO! This was so hard when I first started my business. I really struggled with this. I would say yes to helping a friend out during the day. I would say yes to every client who wanted to work with me. I just always said yes and it hurt my business. Learn to say no. When I stopped saying yes and I started saying no to anything that wasn’t in alignment with my mission, vision, and goals, growth happened.


13 – Set work hours. I used to work endless and endless hours on end. It was ridiculous and to be transparent I got the same amount of work done that I do today. Work expands to time allowed. Create work hours and honor them NO MATTER WHAT.


14 – Be kind to yourself. It literally took me 13 years in business to learn this and it probably one of the hardest things to learn, in my opinion, being in business is hard and it can be lonely. Many people who work the typical 9 to 5 don’t get the entrepreneurial struggle and for me, I found I would beat myself up, when I would fall short in a goal or when things didn’t go as planned. The most important things is to be kind with yourself, set realistic goals, and be willing to adjust. Most importantly, enjoy the journey.



These are the 14 lessons I learned in 14 years and business. I hold these lessons near and dear to my heart. My entrepreneurial journey, like many others, has been a roller coaster ride. I love and embrace every single piece of my 14-year journey and I look forward to the next 14 years and more! Which lesson are you working on learning in your business?

Jamie Palmer

I'm Jamie, founder and CEO (Chief Education Officer) here at Outlier Marketing Group. We exist to help you succeed in building your brand ecosystem and thriving online. I live in Newport, RI with my husband and 4-year old son and infant. I LOVE entrepreneurship, writing, food, paddleboarding and skiing! Thanks for stopping by and as always if you have any questions feel free to email me at Jamie@outliermarketinggroup.com.

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