Lessons Learned from a Serial Entrepreneur

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The year was 1989 and a 22-year-old woman with an itch to challenge herself embarked on her entrepreneurial journey. That woman was me. I was young, shy, enthusiastic and perhaps even somewhat naïve as to the road ahead of me. There were twists, hairpin turns, frost heaves, speed bumps and detours but 25 years later, I’m celebrating the fact that I not only survived, but thriveroad with signsd.

And did I ever learn some lessons along the way!!

Build it and they will come . . .
Probably not the smartest business strategy, but one that has worked for me . . . create a business and then tell others why they need your services! Without a doubt this is a much harder way to start and grow a business, but I believed in what I was offering and that others needed my services. They just didn’t know it yet.

Know thy self . . .
Okay, I admit it – I silently talk to myself. And during those internal conversations I get to know myself pretty darn well. I know most of my idiosyncrasies and enjoy figuring out the rest as they rear their ugly head or take me by surprise! I know that I have a “leadership personality” in that I like to blaze my own trail, not follow others, and control my destiny (and just about everything around me. I’m not proud of some of that but in many instances, such as my brand, my Type A personality has served me well.) I am in tune with what skills I need to develop. I highly encourage others to ask themselves the hard questions, especially what is and isn’t working in their lives, relationships and careers (and what steps can be taken to make it a fulfilling life).

Nothing happens, until you take action . . .
This is self-explanatory. When you are an entrepreneur, you will not succeed unless you get your butt in gear. The jobs won’t get done until you do it or grow your business enough to hire people to do it. Goals won’t be achieved until you set them and take massive action to achieve them. Your marketing won’t do itself until you do it or hire a marketing guru. People won’t flock to your business just because you announced you are open for business. You can build it, but you need to tell them why they need to come! Stop waiting for it to happen. It isn’t going to until you do it.

Feel the fear and do it anyway . . .
When I started my business, I was painfully shy. Sometimes I still have moments of shyness and don’t really like being the center of attention. There is always something on my “to do list” that causes a knot in my stomach. I let myself feel the fear but know that, as the saying goes, “success is right outside my comfort zone.” I push through even though it is difficult, and continuously strive to build up this “muscle” as it is really like a skill one needs to develop. To succeed, you must do the same. Not to mention, you will be proud of yourself!

It’s all about relationships and success isn’t a solo achievement . . .
You cannot become successful by yourself. From family members providing support and assistance to staff, mentors, customers, clients, friends and so on, it takes a village. But you also need to know when to drop some of them if they are holding you back from truly spreading your wings and succeeding. As great as people are, occasionally they get envious of someone else’s success. Don’t listen to naysayers, dream stealers or anyone who tries to bring you down. Wish them well and move on.

Always have a thirst for knowledge . . .
My motto is “end the day smarter than I started.” So much of what I have learned has come from observations, conversations and copious amounts of reading and listening. Information is everywhere. When I started my first business, the internet did not exist. Teleseminars, webinars, podcasts, blogs, etc. did not exist. Self-help and personal development books really weren’t the rage. Now there is no excuse for not expanding your knowledge. In 15 minutes a day, you can read a chapter in a book or article in Success or Entrepreneur Magazine, listen to a recording of a TED talk, read a blog, watch a YouTube video and get your hands on just about anything else that will spread your mind. Do it and make it part of your daily routine.

You are your only competition . . .
I like to have an awareness of what is going on around me, especially with businesses. I like to study the good, bad and ugly ones across all industries. I learn from them and use them for inspiration. I do not, however, pay any attention to what others are doing who are in my line of work. Watching them or concerning myself with them just takes precious time away from building my own business. Think about a marathon – if you are turning to your right or left or even glancing over your shoulder at what others are doing, it keeps you from moving forward with speed and clarity. The same is true with careers and businesses. I am my biggest competitor and I constantly try to “one up” myself.

Become a self-management super hero . . .
I have studied my habits and the habits of others, especially as it relates to focus and time management. This is always a work in progress for me and truly something I have to be mindful of each day. Ideas for managing your time could be another blog post (or book), but I will summarize it as: eliminate chaos, set priorities, block out the unnecessary, take charge of your schedule, chunk it down, minimize distractions, focus and don’t try to multi-task and get sh*t done! No excuses.

Enjoy the journey . . .
Really take in everything that is happening around you. Rather than be upset that you are aging, embrace where you are at because it is pretty awesome to be alive. Be grateful and show it in everything you do. Know that your destiny is in your hands (I know, everyone preaches that, but it is true). You are 100% responsible for your life and rather than be miserable and unsatisfied, do something about it and rather than rushing through life, settle down and take it all in. Enjoy it or change it!

I am so thankful for all that has come my way over the last 25 years and those who influenced me and made me become the person I am today. It has all led me to now and I can’t wait to see what’s next.


Leslie Sturgeon is an award-winning entrepreneur who is the Founder and Visionary of Women Inspiring Women. WIW is now recognized as the largest organization for women’s empowerment, personal development, business resources and networking in New Hampshire.


  1. I have know you for many, many years, and the change in you is incredible… I remember walking into your office when you first started in the insurance building!!! You should b so very proud of yourself for what you have accomplished. But more than that, the assistance you give to people along the way. The sharing and promotiing – the enhanced thought processes you share.. I loved being a part of one program along the way and hoped that I helped others in some small way. Like you, I love what I do, and try to help others as well…but first you have to get yourself there! Best always.

    • Leslie Sturgeon says:

      Oh Nancy – your comments touched my heart. Thank you!! I don’t want you to think I’m a stalker or anything, but you were one of the people I observed over the years as someone who had class, grace, brains, balls and great success. That is why when I did my first ever panel discussion on success and motivation, I reached out to you. Such an inspiration to me and all other women in central NH and beyond.

  2. Leslie, I love how you’re sharing so much of yourself with us. You’re a great role model & provide inspiration for everyone … it’s a privilege to know you & call you my friend.

    • Leslie Sturgeon says:

      Thank you, Tina. Sometimes over-sharing can be disastrous and risky, but it is a chance I’m willing to take to be authentic . . . and perhaps inspire others to do the same, say it like it is, and wear their flaws on their sleeve (and give them permission to celebrate their successes, too). I’m honored to call you a friend as well 🙂

  3. Thank you Leslie. So well said, very relatable and inspiring. I have thought for sometime, when I hear women complain about xyz in their lives, either find a way to enjoy it or go do something to change it. Complaining isn’t going to improve the matter, nor will talking negatively about someone who has accomplished what you haven’t. I appreciate you shooting straight.

    • Leslie Sturgeon says:

      Thanks for the comments, Regina. Clearly you and I both agree that people need to get in touch with their lives and recognize that they are the only ones who can control the direction of their life. And either accept it and be happy with it or change it. The more we talk about it, the more we can spread that message – hopefully it will inspire others to be introspective, retrospective and proactive 🙂 Thanks once again.

  4. Donna Keeley says:

    Leslie, you have always inspired me and I miss our interactions….I am coming back on my own and will see you next week!!! Thanks for the honest, candid, from the heart post!

    • Leslie Sturgeon says:

      Donna – sounds like you have some news, my friend. Let’s chat 🙂 Miss you oodles as well!

  5. Denise Morin says:

    Leslie, I admire your strength and perseverance. You are always coming up with great opportunities for women to learn and have fun! Thank you for sharing your thoughts under “Feel the fear and do it anyway . . .” I , too, am “shy” many times, yet look at the profession we are both in, lol! I honestly think you should write a book about your journey. I’ll buy the first copy!

    Your friend and Colleague,

    Denise Morin

    • Leslie Sturgeon says:

      Your comments touched me, Denise. Thank you for that gift. I enjoy talking about the shyness because (1) it helps me to overcome it, (2) let’s people know that it is okay to admit it – that many of us unsuspecting ladies struggle with it and (3) that focusing on overcoming the shyness, even if uncomfortable, keeps us growing and moving forward. We’re all in this together! As you know, people often think that those of us in “public” roles are 100% comfortable and we are not. Also, sometimes confident women who seem to have it all together are really scared to death on the inside – that has helped me understand aggressive women more and be more compassionate vs. judgmental . . . rather than be irritated they are coming on strong, I remind myself that that may be their mechanism for overcoming anxiety and fear. Thank you once again, Denise!

  6. Leslie,
    It’s been a long journey and I have admired you during the whole thing. You ate so resourceful and clever. I wish I could write and express my thoughts as well as you do. You really do have a great talent.

    • Leslie Sturgeon says:

      Thank you, Ruth. You are another strong woman I have admired over the years – hard working, dedicated and able to jump any hurdle that comes your way. You have set a great example for not only me but other central NH women! And you are a lot of fun, too 🙂

  7. CONGRATULATIONS, Leslie, on 25 years! You inspire me constantly with your energy and creativity. I am SO looking forward to a time when I can become more involved in your events and get to know you better. From one business owner to the next, I honor you. Keep up the great work making this world a happier, healthier place! Love, Pasha Marlowe

    • Leslie Sturgeon says:

      Pasha, I know how busy you are so appreciate you taking time to read the blog and to send me such a sweet message. I have admired your business acumen immensely and your willingness to help others in whatever area of their life they need some TLC! I look forward to the time when we can get to know one another a little bit more! Hugs!

  8. Leslie,
    You touch peoples hearts and that is the most important aspect in building a business. People look up to you and want your advice because they know you will tell them the truth and will help them.
    What a great and powerful article, Thank you
    JoAnne Stapf

    • Leslie Sturgeon says:

      JOANNE!! That got me all misty. Thank you so much. I like people to be straight shooters with me so like to be with others, too. We are all in this together really. I am honored you took the time to read my blog and write such touching words.

  9. Thank you, Leslie. You were my 15 minutes of greater knowledge for today 🙂

    Thanks for the reminder of all the things we should know but so easily forget in this busy world when we’re all trying to forge our way.

    Teresa Troy

  10. Leslie, you are such an amazing role model to me and many many other women! Thank you for sharing your heart and always being so real and down to earth. I’m so very glad to know you and continue to learn from your pearls of wisdom. Hugs!! Jamie

  11. Melanie Patterson M.A. says:

    Leslie, thank you for this! The part about competitors was much needed. I don’t usually look at my competitors too. I’m just doing my thing, but then I think, “I probably should see what they’re up to!” (I guess it comes from the training of writing business plans, you do need to know who your competitors are, but you don’t have to stalk them!)
    When I do get tempted and peek, I instantly start comparing and thinking I better do something differently, even though I’m thriving and happy and my clients love me and are getting results!
    I’m not going to peek or compare anymore!

    • Leslie Sturgeon says:

      Keeping our finger on the pulse of the industry is important and we occasionally need to check out the competitors. But paying all our attention to them is counter-productive as you know. If it keeps you on your toes, that is all good. Finger, toes – guess I’m all about body part references today! oxoxo


  1. […] I love reading posts by other business owners sharing a window into how they run their business and lessons they have learned along the way. Denise Duffield-Thomas at LuckyBitch.com writes really great posts like these every year, Alexis Grant just wrote one and my friend Leslie Sturgeon recently shared lessons she has learned after 25 years as a serial entrepreneur. […]

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