Dear Aspiring Entrepreneur,
So you’re thinking about going it alone and starting your own business. Perhaps it’s something you’ve always dreamed of doing. Perhaps it’s a hobby on the side begging to take center stage. Perhaps it’s a brand new venture. First, and most importantly…good for you! It’s easy to be lulled into complacency by the familiar. If you’re reading this letter, my suspicion is that you’re the type of person who refuses to incorporate “common”, “good enough” or “average” into your vernacular. Greetings, kindred spirit.
Choose to accept this challenge and discover your inner entrepreneur and you’ll embark on a journey that will fundamentally change who you are and how you see the world around you. Scared? Good. You should be. A healthy dose of fear will keep you on your toes, push you to do your best and, probably most importantly, keep your ego at bay, at least for a little while, encouraging you to learn all you can. Choose to explore the uncharted territory beneath those feelings of fear and discover the gift of excitement lying in wait. Welcome that excitement with open arms.
Whatever your venture of choice, this is an undertaking you should take very, very seriously. Give it the time, the thought, the planning it deserves. It will likely take longer, more money and more energy to accomplish your goals than you ever anticipated. But rest assured, no matter the outcome, the journey will be well worth the effort because, at the end of the day, your growth and perspective will catapult you into a level of resourcefulness that will serve you for life.
The name of the game is action. Set out a plan for yourself and follow it. Reject analysis paralysis. You’ll never know it all, so polish up the basics and get moving, one step at a time.
Not everyone will support your decision or understand why you’re choosing to leave the security of the known to put it on the line and risk a shot at the entrepreneurial life, the unknown. Some people, even those who know you best, may look at you with skepticism. Bring it on! Not everyone is cut out to be an entrepreneur. Your job is to believe in yourself and find others who believe in you to support your efforts along the way and pick you up when you fall. It takes an amazing amount of courage to break out of the mold and carve your own path in this world. I commend you and encourage you on this journey.
With you in mind, I humbly bring you the top tips I’ve personally learned along the way, most of which stem from learning the hard way. Items with asterisks will be discussed in more detail in future blog posts.
1) Read Start with Why and figure out YOUR “Why”. Ensure any business venture you undertake closely aligns with your “Why”. When you know your “Why”, you’ll be able to hang in there when the going gets tough and make your mark on this world, inspiring people as you blaze a trail.
2) Read E-Myth by Michael Gerber and Rich Dad, Poor Dad by Robert Kiyosaki if you haven’t already. They’re quick but important reads.
3) Have a plan. Try Palo Alto Software for business planning software. Know where you’re headed. Once you figure out your plan for getting from Point A to Point B, put it to the side and plan it all over again from scratch, not using any of the same steps. Once you’ve done this, set that aside and then do it again. Why? Because when you hit a roadblock, you’ll have a plan “B” and a plan “C” to fall back on. It’s preemptive flexibility that you’ll be grateful for in the long run (thanks to Steve Linder for this idea).
4) Choose your partnerships carefully. Whether a business partnership or a key vendor, choose cautiously and choose well. There’s a reason they call it “Due Diligence” – it’s something you MUST DO!
5) Know how to write and read a contract. Be diligent in doing so.***
6) Start as you wish to end up. Don’t want to be tied to your business in 5 years, where nothing can happen unless you’re at your desk? Design it from the start so you have the systems in place to allow your business to run without you. A great exercise is to graph out the organizational chart of your future business 5 years from now. ***
7) Document everything. For really important conversations, record it. ***
8) Know the basics of all the aspects of your business, especially the finances. Even if you’re not a numbers person, educate yourself to a basic level. Sometimes it’s really just a numbers game but you need to know the rules of that game to recognize when the numbers don’t add up. ***
9) Start small but dream big. Know your long term vision and goals and start small. Do fewer things and do them incredibly well. Then expand, building on your success. Bite off more than you can chew in the beginning and you’re in for a rude awakening.
10) Stay true to your integrity. If you don’t have the highest levels of integrity then please, do us all a favor and don’t even throw your hat in the ring. Refuse to deal with anyone whose integrity you question, which brings us to the next point.
11) Trust your gut. Ignore this rule at your peril. If a contract, business partnership or direction doesn’t “feel” right, it’s probably not.
12) Read The Dip by Seth Godin. Knowing when to quit and when to hang in is critical for an entrepreneur.
13) Evaluate yourself on a regular basis. Schedule it. Stick to it. By getting this objective view regularly, you’ll make better decisions, able to check your emotions at the door.
14) Use social media tools. They’re predominantly free and incredibly powerful.***
15) Use the appropriate level of technology. You’re not NASA. You don’t need a phone system for 15 people if it’s just you, even if it does have lots of cool bells and whistles.
16) Network. Find a supportive group of like-minded people. This will increase your access to great and creative ideas, as well as moral support and years of experience in a variety of areas. You’ll know these people when you find them because you’ll feel like you’ve finally found your home.
17) Learn about general Project Management principles. Most of the items with asterisks above have something to do with these principles that we’ll be discussing in more detail over the coming weeks.
I leave you with this quote from Marianne Williamson:
“Our deepest fear is not that we are inadequate. Our deepest fear is that we are powerful beyond measure. It is our light, not our darkness that most frightens us. We ask ourselves, Who am I to be brilliant, gorgeous, talented, fabulous? Actually, who are you not to be? You are a child of God. Your playing small does not serve the world. There is nothing enlightened about shrinking so that other people won’t feel insecure around you. We are all meant to shine, as children do. We were born to make manifest the glory of God that is within us. It’s not just in some of us; it’s in everyone. And as we let our own light shine, we unconsciously give other people permission to do the same. As we are liberated from our own fear, our presence automatically liberates others.”
With You in Spirit,
A Fellow Entrepreneur



Thank you for a wonderful set of suggestions to inspiring entrepreneurs. I agree with most of your recommendations. The only exceptions are that I have a different favorite planning tool and you shared one book that I haven’t read, yet. That book will be on my list of holiday purchases for my self.
Thanks for sharing your excellent insights.
Shallie Bey
Smarter Small Business Blog