Have you ever thought about what it would be like to truly pursue your passion and make money doing it? Women are leaving corporate america at twice the rate of men to start their own businesses. I found myself contemplating that in early 2010 as I found myself yearning to pursue work that I loved that would help me make the impact I wanted to make.  Before I left my 20-year corporate career in late 2010, I took the time to plan the launch of my leadership development company.

I talked to lots of entrepreneurs about what I needed to know. I got lots of good advice: Make sure you have enough cash flow to support yourself for a year.  Make sure you have a strong business plan. Get your 60 second elevator pitch right. Make sure to differentiate yourself in the marketplace. What follows are ten surprising things I discovered that no one told me about. Read on and see if they resonate with you.

1) Know how you will leverage your passion  Steve Jobs said, “Being the richest man in the cemetery doesn’t matter to me. Going to bed at night saying we’ve done something wonderful, that’s what matters to me.”  Entrepreneurship is not just about the money. It’s about an idea that you are committed to seeing to fruition. Entrepreneurship is tough. It requires our full dedication. It causes us to stretch ourselves to be more resourceful, more courageous, more resilient than we thought ourselves capable of being.  So make sure that when you identify your business idea you understand how you will leverage your passion. My passion is being a catalyst for transformation – it’s when the light bulb goes on for my clients and they discover new insights about themselves and are able transform themselves and their organizations.  Find what aspects of the work you will be doing that you love to do. Define your personal brand to help you get clarity on this.

2) You actually need to take the plunge It was tempting to be in planning mode until I had it perfectly figured out.  It was tempting to wait until I was sure the economy had really turned around. What I discovered is you can be in planning mode forever and sometimes you just need to take the plunge. Our fears hold us back from plunging in. We all have fears. We need to plunge in with them. I love this quote from Martin Luther King: “Take the first step in faith. You don’t have to see the whole staircase, just take the first step”. What I discovered is that once you get really clear and committed to your business idea, the synchronicity starts to work for you. This doesn’t mean you don’t need to work hard. You do!

3) You need to have a plan.  And you need to be ready to change it. For someone who was so used to creating and approving annual plans in my corporate roles, it was incredibly hard to create a revenue plan for a business I had not been in. I didn’t have a baseline from last year or learning about what works and what doesn’t from personal experience.  But I forced myself to create a plan nonetheless.  It’s useful to have a few things clear. Who is your customer? Why will they want your product? How much can you charge? What kind of money do you need to make to support yourself? Don’t worry about having the perfect plan. But you must have a revenue and expense plan and review it every few days. What I started with in terms of where I would get my revenues, and what I ended the year with are pretty different. The lesson I learned was to be flexible. I learned to befriend uncertainty and start to develop a wider lens for opportunity. Things never turn out the way we plan them, and that’s not all bad!

4) Karma works – make friends and influence people  I thought most business development decisions are made based on your 60 second elevator pitch and your differentiation strategy. My experience this year tells me that 100% of my business came from referrals and relationships with people I had developed prior or during this year. Sure, I need to be good at what I do. But, people are willing to refer me because they like me. They like me because I am genuine about helping them when I can without any expectation of return. It’s good business karma and it works!

5) Ask for 100% of what you want and don’t take it personally when you don’t get it  In my first few months it was hard to ask for business. After all, how can you not take it personally when what you’re selling are your own services and a potential client says “No”? My epiphany moment came when I realized that by deciding not to take things personally, I could actually free myself up for asking for 100% of what I wanted. What was preventing me from asking boldly for what I wanted was the fear of rejection. The simple question I ask is “How can I be of help to you?” I decided that I would interpret all “No’s” as “No, not now”. Plus, being of service to others is a huge part of the psychic income I derive from the work I do.

6) Find your Beginner’s Mind This is corollary to the point in #3 about befriending uncertainty.  The greatest advantage we have being new to our business is… being new to our business. We have what Zen Buddhists called “A Beginner’s Mind” – a blank slate, a fresh perspective that allows us think more openly and broadly and creatively and to try new things.  At the risk of finally being diagnosed with attention deficit disorder, I am trying lots of different ways of building my business – the radio show, blogging for The Glass Hammer, Mentor Moments TV, networking. It allows me to learn what works and what doesn’t. Keeping that Beginner’s Mind to continue to view things from a fresh perspective is important as the world around us changes quickly.

7)  Fire Your Inner Critic. Find Your Inner Coach You win some, you lose some. The ability to give yourself a pep talk when you’ve “lost some” is really important.  The biggest secret to long-term business success is to actually stay in the business long-term.  This might seem overly obvious but it is true. When I fail at something, I need to give myself a pep talk, mend the broken ego, and move forward.  I cannot afford to dwell in misery. Surround yourself with people who will lift you up, give you honest advice and a hug when you need it.

8) Make Every Penny Count. One of the best definitions of entrepreneurship I heard recently is “the pursuit of opportunity regardless of resources”.  I have learned how quickly money slips through our hands when we aren’t watching it. Being a Finance MBA and coming from a family background where frugality was encouraged, I have learned that I need to be careful about where I spend my cash. I had the luxury of planning my transition to being an entrepreneur and was able to set aside cash flow to support me in the early 12 months of my business. This is crucial for any new entrepreneur. You don’t want to be so desperate that you give up too early or give away your services for less than they are worth.

9) Cultivate An Opportunity Mindset – I must confess I am naturally an incurable optimist. I always look for “what’s the opportunity here” in any situation. It helps me be more resilient in the face of challenge and failure. Life is a series of unfolding events and we have great power in how we choose to respond to the events that present themselves. Sure, I have my “woe is me” days when I don’t get a client I really wanted and worked hard for. But then, I rebound by affirming a knowing that the clients that are mine will come to me and the others will go to who they are best suited for. My job as an entrepreneur is to be in action to pursue opportunities and let the results be how they are.

10) Follow Your Bliss. One of the principles I have decided to live my life by is to move toward people, places, activities that create great positive energy in me and to use the activities that inspire me to grow my business.  One of the activities I really enjoy is connecting with people and learning about their stories.  The opportunity to do a radio show fell in my lap. I created a show called Transformational Women. It helps me connect with amazing women who are transforming their organizations and helps them share great nuggets of advice. It is great fun and helps me to make friends (see point #4) as well as give back to younger women who can benefit from the advice.  The learning here is to look for ways to grow your business that create positive energy in you. It creates a virtuous circle of fulfillment and success.

If this resonated for you, please comment, subscribe and share with others.

Additional Resources:

Define your personal brand: The Authentic Brand: YOU

Harvard Business Review blog post by Daniel Gulati: The Top Five Career Regrets

To fire your inner critic: Coaching for your Inner Critic

To learn resilience from failure: Leadership Lessons in How to Fail Well

Showing 9 comments
  • Sarah Haider

    Thank you for this candid learning, I whole-heartedly agree that a positive attitude and being open and flexible to the possibilities, instead of insisting on limitations, is what makes the difference between success and failure. The practical details of life aside, the thing that differentiates successful entrepreneurs from others is their ability to believe and cultivate their own success!

    I am sharing it with my other entrepreneur friends and asking them to review and respond to the article.

    • henna

      Thanks Sarah for joining the conversation and also sharing it with others!


  • suneel kumar

    thanks heena for such spendid wrok , the most i love abt u is to help people it wonder ful to realise we r here to enrich hearts and minds of other people beyond our profit and business motive, i repect ur idieas coz i belong to same school of thought sufi . i need ur comments in Global economy majority of firm and busniess man r doing to expliot nature and relation and use them like commdity when it useful ness is no needed further to discord it what is your opinon ?? how we overcome this problem

    • henna

      Thanks Suneel for your thoughtful question and comments. There is a great movement called Conscious Capitalism and others of its type that organizations and leaders are driving. You can learn more about it by searching for it on the internet. It will connect you to practices that organizations are employing to bring more of a sense of responsibility for the earth, other people and our connected communities. Other that that, each of us can choose to interact with others in ways that promote peace and connectedness in our daily lives. Best wishes to you and the work you’re doing.


      • suneel kumar

        thanks Heena for ur kind comments and taking out time i really appricaite ur views and style of leadership i have study lot regarding leardship but most of time its all abt managemnt , goals , and commerial profit it all semms surface of leardship i belive in spritulaism indept beyond time and space yet i am not aware of cosncious captilism by theory what i guess it is abt professianl ethics ?? please kindly correct me if i am worng . l like ur style of leardship and the way u articulate ur point it is so perfect i understand hidden dimesion of the words it never happen before me ! i think u have great talent above all ur blessed with enrich soule inside embed in ur personality who has help nature and kind heart . take good care of ur health.

  • Raj

    Good Initiative in practical!

  • Karin Jones

    Dear Henna,
    Wow what a breath of fresh air! I found you through a common membership in Beta Gamma Sigma. You commented in blog post asking for comments on career we regrets. I love your style of writing. It makes so much sense to connect with people through your personal stories. Shown many leadership pieces are much more high and mighty. Your style shows that the true way to connect and resonate with people is to come from a place of personal vulnerability. Keep sharing and I shared your piece on working with your in a critic on my Facebook. I decided that my coach is actually a coaching team. I love the idea of yours of using a teacher of yours. Since I lost my mom when I was very young I have several key women over my lifetime who have been supportive and loving. I also have memories of an incredible teacher, John Ansty, at my school who was 100% there for me in high school. He’s definitely on the team. I still haven’t figured out a persona for the inner critic yet. I’m working on that one. Putting faces to the inner critic and also the coaching team will really help me. I’ll keep you informed. Stay tuned…

    • Henna

      Hi Karin –

      Thanks for taking the time to share your insights, and also a bit of your personal story. You are right, our personal stories connect us to each others’ humanity. Thanks also for sharing within your tribe. My best to you and keep the insights coming.


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  • […] my own business at the height of the recession. I can honestly say that a year and half into my business, I still have my fears (including moments of utter panic). Here are some leadership practices I […]

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