5 Things I Wish I Knew Before Leaving Corporate Life and Starting My Own Business

Part of Kathy Caprino's series "Supporting Today's Workforce"

I spent 18 years in corporate life--in marketing, product development and membership services--and experienced some great successes that I’m proud of. But I also faced some dismal failures. The failures weren’t around outcomes I generated or projects I launched – for the most part, those tended to go well. The failures centered around my emotional and physical well-being, how I was treated, how I treated myself, and the lack of integrity, meaning and purpose I felt doing work that wasn’t aligned with my core values with people I didn’t respect or trust.

After a crushing layoff from my corporate life in the days following 9/11, I transformed my career, first becoming a marriage and family therapist, then a career and leadership coach/consultant, writer, speaker, and trainer. I launched my coaching and consulting business in 2007 and have never looked back.

I know now that I’m much more suited to entrepreneurial life and running my own business (and always have been) than serving in the corporate world, which was challenging for me literally from the beginning. While I love my current work intensely and am deeply passionate about it, I have made some truly damaging business mistakes along the way since leaving corporate life. One of those was thinking that just because I’d been a senior corporate marketing executive, with high-level experience managing large budgets and initiatives, that I had the know-how out of the gate to successfully lead and grow an entrepreneurial venture. It just wasn't true.

There are a good many things I wished I’d learned before launching into an entrepreneurial life that would have helped me bypass the serious challenges I faced. I’m not sure I would have listened to that advice back then, but I would have been better equipped certainly, if I had.

For an insider look at what I wish I knew before becoming an entrepreneur, check out my Finding Brave podcast episode on this:

The top five things I wish I knew before launching my own business are:

Know your tendencies around money, spending and saving

In my therapy training, I learned that couples tend to have complementary styles around money. We call it the “spender-saver” dynamic, whereby one partner tends to feel very comfortable spending money freely and in the moment, while the other prefers saving and thinking about the long-term implications of their expenditures and their money situation before spending.

Before you launch you business, get very clear about your relationship with money, and become more empowered in it, because if you’re an extreme case at either end of the spectrum, you’ll have some real challenges in your business.

People like me who are “spenders” tend to go with their gut and spend more impulsively, and that can backfire in business. One personal example: When my first book Breakdown, Breakthrough published, I felt so strongly that it would be a bestseller and generate lucrative business for me, I invested $30,000 in publicity and PR, despite some sound advice from a few folks I should have listened to.

While I received some wonderful press coverage from the publicity work we did (including a great piece in the Wall Street Journal), the financial return on the investment was very little. Had I taken a step back and understood my penchant for spending big--and my chronic resistance to being financially prudent--I would have considered scaling back that investment, or approached it in a phased, measured way rather than committing to a big sum of money before understanding the financial realities.

I've seen that "savers," on the other hand, often won't part with their money to save their lives, and they hold themselves back from investing in themselves or in critical projects that would accelerate their growth.

The key is to be balanced in your thinking. Today, for instance, with my new book The Most Powerful You, I did invest in great PR and media help, but the sum I invested was sound and reasonable with a solid chance for a strong return on investment.

Tip: Get intimately familiar with your money story, (read the book The Energy of Money by Maria Nemeth and do the exercises, as a start) and understand your relationship with money. Most mid- to high-level professionals and entrepreneurs I work with (yes, even wealthy ones) need some powerful work around how they operate with and relate to money. Get some outside advice from a mentor, financial consultant or accountant or business growth specialist you trust before investing in a big way in a direction that is unsure for you. And understand that you’ll most likely have to spend infinitely more money launching and building your business than you ever imagined. Take a good long look at how you will fund your transition, and don't just center your business strategy around a "build it and they will come" mentality.

Your partners can uplift you or crush you – be very careful.

Before I knew about narcissism, I fell into the trap of repeatedly developing (and attracting) relationships and partnerships with highly manipulative, narcissistic people. I didn’t understand what was happening at the time – these individuals simply seemed to shine brighter than others, and they were charismatic, exciting, talented and thrilling to work with, for a time.

Sadly, in numerous cases, these individuals turned out to be extremely narcissistic – unable to be challenged, acting as if they’re above any rules of conduct or standards of integrity, and were obsessed with expanding their own personal success and stroking their fragile egos, at all costs. The truth is that there are many narcissistic people in high levels of leadership and management in our world today.

My therapist friend and colleague Janneta Bohlander who works with adult children of narcissists says that for many people who’ve experienced narcissism in their childhoods, “their picker is broken,” meaning they can’t for the life of them choose well when it comes to partners. But we don’t have to be involved with narcissists to know that the person you choose to partner with will be extremely instrumental in your ability to succeed and thrive.

Tip: Be very careful about the business partners you choose. Look more deeply than just the surface, and make sure that they have the kind of integrity, honesty, emotional maturity and balance, compassion, strength and openness to make a great partnership thrive. And if you're dealing with narcissism in your life and work right now, check out the 6-part webinar training series that Janneta and I co-delivered on Dealing with Narcissism and see the free resources at the bottom of that page.

You have to learn to be a leader, not just a manager or “doer.”

When you’re running your own business, you don’t have a boss to run things by. You’re the boss, and you’ll need to become a true leader in that role who not only manages the business well, but has the visionary capacity to see (and invest in) the future before it’s “hatched.” And you’ll need to lead your endeavors with confidence and authority towards that future.

The terrific book The E-Myth Revisited by Michael Gerber talks about why so many small businesses fail – because small business owners make the fatal assumption that doing/offering a particular skill or service (like coaching, graphic design, baking, etc.) is the same thing as running a business that offers that service. The two are radically different, requiring completely different skills, mindsets and focus.

Tip: Before you enter entrepreneurial life, take steps to build leadership capacity within yourself. Make sure you’re not making the mistake of thinking that being a “doer” rather than a leader will be enough. Strengthen your decision-making process, and build your core confidence and authority in trusting yourself and your abilities and ideas. Speak up and take a stand more often. And take a deeper look at why you want to launch this business. If it’s because you love to coach (or bake, design, write copy, etc.) but suspect that you’ll hate running the business side of offering your skill or service, then there’s more work you need to explore this direction and "try it on" (physically, emotionally, behaviorally, financially, etc.) before embarking on it.

Change and pivot more quickly when the need arises.

In my corporate life, even as a VP, I generally wasn’t the one who decided on the high-level strategic direction of the businesses and products I oversaw. That was the realm of the senior VP and the president. Even in what appeared to be a high-level job, I wasn’t responsible for making the big, over-arching decisions about when we should pivot out of an industry or change directions in a significant way.

Without any real experience in making these decisions, one of my biggest challenges as an entrepreneur has been to recognize when it’s time to pivot and change, and having the guts to do it.

As an entrepreneur, you have to make these important decisions very regularly. Just a few of the hundreds of questions you’ll need to ask, and address, include:

• Is it time to pivot away from this type of service/product I’m offering? How do I know?
• Should I throw everything out and start over or make incremental changes?
• Should we stop using marketing agencies and go with a different model of staffing and support?
• Should I restructure my business and build programs that are more passive-income based vs. direct, client-facing initiatives?
• Is the niche we’ve targeted truly the right one for the work we’re doing now and where we want to go in the future?
• Is how we're currently generating/attracting customers and clients the right way for our business model?
• Do I have the right team in place to help my business grow and strengthen, especially through these challenges times? (This is where I see so many business owners fail every day to make the tough decisions and act on those decisions.)

And the list goes on and on.

Tip: Before you leap to entrepreneurial life, begin thinking about and tackling (wherever possible) those types of strategic questions in your current work that will shape the direction of your products/services. Close your power gaps and start becoming the leader you want to be. Evaluate the key leadership decisions that can and will impact your company’s success. And use your voice more powerfully.

(For more about what to fix in your entrepreneurial business today to build more success, check out my Finding Brave podcast interview with Mike Michalowicz on Fix This Next In Your Business.)

Finally, as an entrepreneur, you’ll be constantly bombarded with advice from outside experts, and much of it will be bad.

Just spend an hour online looking at sites geared to entrepreneurial growth, and your head will spin with the different (and often contradictory) advice you hear.

To be a successful entrepreneur, you have to learn how to think for yourself. You’ll need to prioritize powerfully what you believe in and care about, despite fierce pushback, and in the face of others saying you’re crazy or misguided.

And you have to be brave and confident enough, and build strong enough boundaries, to stand your ground when you know beyond doubt that what you want is risky and going against the grain of what so many “experts” tell you should do.

If I had listened more to what I knew deep inside about how I wanted to operate as a business owner and entrepreneur, rather than be swayed by listening to outside “experts,” I would have saved myself a lot of grief and wasted time and money.

Tip: Whatever your role is now, start developing a stronger trust in yourself. Develop a keener ability to sense and ascertain when things feel “off” and of what you believe. And make yourself right not wrong about your feelings, ideas and intuition. Become a true leader in your own life. But also, "get hip to your own trip" and become clearer than ever where your chronic thinking and behavior may need to be reassessed.

Let’s face it – 

the people who’ve changed our world the most and innovated in ways that reshaped how we live, work and think, followed what they knew to be true, not what others told them was right.

Wherever you are in your career, believe in yourself without doubt, but also surround yourself with great, knowledgeable (and emotionally healthy) mentors, advisors and partners who are in harmonious sympathy with your ultimate goals for your work and business. Strike a healthy balance between trusting yourself and getting help when you need it.

You can have the success and impact you want in your entrepreneurial venture, but know it's a journey of self-empowerment that's needed first, of closing your power gaps, and not shying away from engaging in the internal and external work to become the most powerful impactful version of you that you can be.

To become a stronger leader and contributor in the work you're doing today, read my new book The Most Powerful You: 7 Bravery-Boosting Paths to Career Bliss and tune into my weekly Finding Brave podcast.

?For hands-on help to build a happier, more successful career, join me in the Fall session of my Amazing Career Project online course, or work with me in a private Career Breakthrough Coaching program.