Do What You Love And The Money Will Surely Follow, Right? No, Not Right

The blind spots people have regarding career reinvention and entrepreneurship touch on a complex array of issues including money management and more.

Do What You Love And The Money Will Surely Follow, Right? No, Not Right - Lioness MagazineWhen I was locked in my unhappy corporate career, I dreamed for years of getting out and doing something I was deeply passionate about that felt meaningful and purposeful. But figuring out how to do that on my own seemed impossible. Trying to identify natural talents that I loved to use and then monetize them in new direction was daunting to me. I just couldn’t figure out a new path that would not require my starting over completely.  I certainly didn’t want that (who does?).

When I finally made the leap after a brutal corporate layoff in the days following 9/11 and embarked on a 10-year business-building journey, it was fraught with mistakes, pitfalls and blind spots. In fact, it took me many years to realize something huge – that I actually wanted to be a successful entrepreneur, not a “technician.”

I originally thought I’d be happy leaving my corporate life and becoming a “technician” of sorts – a private practitioner. Like others I’d seen, I thought I’d enjoy being of service using a strong skill set (which turned out to be therapy, coaching and consulting for me) from which I could build a thriving practice. But five years down the line, I suddenly woke up to the realization that this path had lost its shine and excitement. Instead, it was a successful entrepreneur I longed to be, not someone stuck in the never-ending loop of offering one-on-one, paid-by-the-hour or project work. I suddenly longed to scale career transformation and growth in a very big way. And that led me to another finding – that it’s impossible to scale bigger if you insist on needing to be in the loop directly with all of your clients and customers.

On the road to launching a successful small business and working with people who are doing the same, I experienced another blind spot that so many would-be entrepreneurs have. That’s the notion that we can just “Build it and they will come.” Or, another way to think of it is this: “Do what you love and the money will follow.” I’ve seen over and over that,  in business and professional life, money doesn’t just “come.” We have to continually and courageously take certain types of empowered actions from certain types of empowered mindsets in order to generate great money building a business we love.

In working with professionals to “dig deep, discover their right work, and illuminate the world with it,” I’m seeing how confusing it is for people who have a big dream. They want to believe they can make a lot of money doing work they love, but so many fail at it and don’t know why. Others have bought into the false, damaging information out there today that you can be a millionaire in a few short weeks with your new online business, or you can write a book or program and at the drop of a hat, become a wealthy, famous expert and speaker, and so on. Sadly, the online world preys on desperate dreamers.

The blind spots people have regarding career reinvention and entrepreneurship touch on a complex array of issues  including money management, support, marketing, community-building, branding, financial planning, product development, leadership, risk, timing, and much more. And when people make public and costly mistakes in these areas, there’s a lot of shame and embarrassment, and they often experience a marked dip in confidence and self-esteem. We tend to berate ourselves and believe we’re the only ones stupid enough to fail at an idea we originally thought was so brilliant.

If you can uncover these blind spots before embarking on your new business or reinvention, and take the blinders off now, you’ll succeed in a much quicker, deeper and more satisfying way.

Here are five blind spots to be aware of and navigate through in order to make a great living doing work you’re passionate about:

You believe that because you’re good at a certain skill, you’ll automatically become a financial success running a business that offers that skill.

As Michael Gerber points out so well in his book The E-Myth Revisited, there’s a fatal assumption that so many would-be entrepreneurs make and it’s this:

“If you understand the technical work of a business, you understand a business that does that technical work.”

Gerber shares,

In fact, rather than being their greatest single asset, knowing the technical work of their business becomes their greatest single liability….The real tragedy is that when the Technician falls prey to the Fatal Assumption, the business that was supposed to free him from the limitations of working for someone else actually enslaves him.

For instance, being a powerful career coach doesn’t translate into running a profitable, rewarding and enjoyable coaching business. These are two very different trajectories demanding different mindsets and behaviors. Engaging in offering personal, hands-on support to help people make positive change (coaching) and building a lucrative business that offers successful coaching programs, services and resources (business management) are two very different (and clashing) endeavors.

Gerber adds,

To build a successful business model, it has to be balanced and inclusive so that The Entrepreneur, The Manager, and The Technician all find their natural place within it, so that they all find the right work to do.

Read Michael’s book and find yourself in the examples – are you trying to be a Technician or a Manager when what your business really needs is a visionary Entrepreneur?

You shy away from having a command of the numbers.

When I interviewed Susan Sobbott, who was at that time the President of American Express OPEN, on the differences between male and female entrepreneurs, she explained that when asked about the numbers of their businesses – the financial forecasts, drivers, and plans – women tend to shy away from owning them. They may say, “I’m not really good with numbers,” or “I have someone else working on the numbers.” That’s a kiss of death in your business. If you’re running the business, you must be intimately familiar with the financials, and be able to speak powerfully about all your business’s financial drivers, budgets and forecasts if you want others to support and believe in you.

If you feel you’re not good with numbers, that’s not an immutable state.  Do something concrete to get better at it. For instance, take a financial management class, or sit with your financial adviser and dig deep to learn the inner financial workings of your business. Until you do, you’ll never be an energetic match with the mindset and actions necessary to earn great money. You’ll always hold money at bay.

You believe that the good word about your work will just organically spread.

So many people who launch an endeavor of any kind don’t understand what’s required today to get the word out. Women in particular seem more resistant about the idea that they have to be their own best and most powerful advocate for their business. There’s a fascinating story that has to be told about your business and why people should care about it. If you aren’t willing to tell it, then no one will care. (Read how Pencils of Promise Founder Adam Braun had to learn this the hard way.)

Promoting and communicating engagingly about your business spreads the word to cultivate believers and customers who will buy into your success and support your company’s growth. Staying shy about your business will kill it before it hatches.

You can’t envision how your business will scale and you’re afraid to even think about it.

In consulting for both men and women, I’ve seen that women’s views of what they are capable of and what they may achieve are often more constrained and limited than what men envision. I believe there are numerous cultural, societal and individual influences that contribute to that, but again Susan Sobbott shares, “Ask a woman if she has what it takes to bring her new venture forward and succeed hugely, and she’ll say more often than not: ‘No, not sure, or maybe.’ Men tend to say ‘Yes!’ without hesitation.”

The challenge for many women is that they are often more resistant to believe in themselves in a huge way, to think big and to scale up  (which requires risk, delegation, an entrepreneurial mindset and engaging in new ways of operation that allow for growth) when the time is right for it. Think about how you feel about scaling your business to a higher level. Do you long to have a bigger impact but just thinking about it gives you a pit in your stomach and makes you feel anxious and worried? If so, there’s inner work to do so you can envision — and build — a more expansive future, for you and your business.

You don’t realize you need some outside help and support.

Finally, I’ve observed that many people in business and in their careers stay isolated and alone on their journeys, and often live to regret it. They don’t get the help, advice, mentoring and sponsorship they need. And in their businesses, they try to do everything alone and in a vacuum.

When you’re launching a new venture, you need empowering help, support and fresh insight. Don’t try to do everything on your own. Sure, in the very beginning you need to be careful who you share your dreams with. But as you’re launching, you need a strong team of advisers – trusted supporters who can offer outside perspective, experience, objective feedback and a knowledgeable sounding board. Build a network of folks you trust implicitly and admire deeply – people who’ve been there and done what you want to, with fabulous success, who believe in your capabilities and want to support you. Keeping your challenges and problems to yourself will only set you up for failure, and for shame and embarrassment as well, because you’ll end up realizing that your fear of vulnerability and your reluctance to share your challenges was exactly what kept your business down.

For more about building a successful, rewarding career of significance, visit and The Amazing Career Project.

This article originally appeared in Forbes.

Photo courtesy of Helmuts Guigo [FLICKR]

About the author

Kathy Caprino

I'm a career success coach, leadership trainer, author and speaker dedicated to the advancement of women. I run a career and leadership consulting and training firm -- Ellia Communications -- that offers programs, training and resources for career growth. A former corporate VP, I'm a trained therapist and career specialist, and have worked with over 10,000 professional women and emerging leaders globally. Along with Forbes, I blog for Huffington Post, LinkedIn, and my own Ellia Communications career blog. My book Breakdown, Breakthrough: The Professional Woman's Guide to Claiming a Life of Passion, Power and Purpose, explores the 12 hidden challenges working women face today and how to overcome them. If my work interests you, please visit my website at

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