The New Entrepreneur


“Don’t be afraid to give up the good to go for the great.” —John D. Rockefeller A poster with this quote popped up in my Instagram feed this week. Like most things do, this poetic thought showed up at a time when I most needed to hear it. I’ve been in a serious period of reclamation for some months now. Reclaiming control over my time, my earning potential, career, my business(es), relationships, my garden, my closet, romance, parenting teenagers, weeds (literal and figurative), reclaiming creativity, happiness, opportunity, fitness, wellbeing, reclaiming professional and personal goals, reclaiming balance over stress and schedule demands. PHEW. That felt really good to say out loud and with gusto! Join me this week as I discuss the new entrepreneur and tips to break free from that old outdated handbook for what “work” is supposed to look like.

The term entrepreneur is commonly defined as a “person who organizes and manages any enterprise, especially a business, usually with considerable initiative and risk.” Remember when Guy Kawasaki wrote, “It begins with a dream that just won’t quit—the once-in-a-lifetime thunderbolt of pure inspiration, the obsession, the world-beater, the killer app, the next big thing.” For most people, being an entrepreneur also means longer hours than you’ve ever worked, more pressure than you’ve ever carried and the slippery feeling of walking on a highwire while juggling flaming bowling balls with no safety net. Having started my own business years ago, I can say that I’ve certainly felt all of those things at one time or another.

While some stressful aspects of owning your own business, large or small, are unavoidable like acquiring capital, developing a competitive brand and charting sustainable growth. Those are simply the realistic costs of doing business on your own terms. However, as an entrepreneur you also have freedom to employ strategies to ease pressure, make work feel like play and help grow your business long term.

Regardless of your industry, here are some universal tips to break free from the old outdated handbook for what “work” is supposed to look like and start living the new entrepreneurial lifestyle:

{one} be an inspiration

Make a date with yourself to brainstorm what you want your business to look like and how it will function? Is a 9-5 gig in a traditional brick & mortar office your ideal setup…does your dream take you to far away places working from any available Internet connection…or is it something in between? Whatever the package looks like, make sure your plan fuels your creativity and drives innovation.


Walk & talk meetings led by my two assistants, Hannah & Charlotte

Once identified, put that plan into action. Every. Single. Day. Creativity and innovation don’t have an “on/off” switch. It is a vibe, an energy that infuses the air around you. If you’re inspired by what you do it is very likely that your target customer will be too.

Re-visioning what you do and how you do it will set you apart from your competition and communicate creativity and innovation without clubbing your target audience over the head with it. Don’t be afraid to turn the rules of your industry on its ear! For example, if your peers are brainstorming in stuffy offices or conference rooms, take your collaboration out of doors.

Years ago I transformed client meetings into “walk & talks.” There are a number of free apps that take notes for you, freeing all parties from the chained-to-a-table feeling. You’d be surprised how much creativity is driven by fresh air and beautiful surroundings. Productivity has gone through the roof making more efficient use of time and resources.

{two} get connected

In an era dominated by mobile devices, Big Data, and social media, recent research indicates that humans crave personal connections more than ever. Emails and shared documents all have their place but don’t rely on them as your primary communication system. Matt Mullenweg, the creator of WordPress and CEO of Automattic (the company that offers a range of products and services for WordPress users) runs a billion dollar company with no offices or email.

In my experience, great work is driven by synergy and that is built around human connection. What entrepreneur doesn’t wake up every day absolutely driven to generate great work!!??!! Pick up the phone. Skype. Initiate a Google hangout. As a professional, there is no better way to deliver excellent customer service or hold a meaningful conversation with a client or collaborator than to have a two-way conversation.

{three} learn to say no

Learning to say “no” in business is a powerful skill. THIS was a biggie for me. Sometimes still is a biggie for me. When you are solely responsible for generating your own income it is very tempting to say yes to every opportunity that walks through the door. This is an ugly sticky trap!

Not every collaboration is going to be successful. Not every client is a good fit for what you have to offer. Not to mention taking on more work than you can successfully complete with the level of standard you wish to deliver sets up the potential for a disappointed client—ultimately hurting your business in the end.

It is hard not to base decisions on the immediate payout. However, cultivating client relationships and projects with the long vision in mind increases the chances for repeat customers. If you get a sense from the get-go that your deliverables do not match what the client is looking for, it is a much greater service to your long-term sustainability to say no. Ed Kelley, one of my most influential mentors, always says “just because you have the ability to do something doesn’t mean you should.” Here are some tips to saying no with grace and authority.

{four} dress for success

Remember when your mother used to drill the importance of making a good first impression into your head? Dress for success, she would say. Well, she was right! For the modern entrepreneur that sage wisdom extends to more than just your wardrobe. Dressing for success is about confidence and pride in a job well done. Believing in your own talent and ability to exceed the industry standard is just as important as the physical “work” clothes you put on in the morning.

Most of us have been taught that humility is a virtue and find it difficult to preach our own Gospel. Yet your very survival depends on it. As an entrepreneur you must be both seller and maker of your wares to clients and to your competition.

Don’t confuse confidence with ego—one drives success and the other kills it. Confidence is a delicate balance between humility and ability. I’ve found that speaking in terms of experience and deliverables infused with enthusiasm for the tasks at hand are a great way to authentically sell yourself and your business.

Be clear about what you can do while also being willing to stretch, grow and challenge yourself to always exceed the industry standard. You’ll stay current and on your toes, in my experience that is the hook that has landed my biggest clients.

IMG_0481{five} have faith

You are never ever ever too old to start something new! If it’s meaningful to you, that is a great place to build the foundation for the next phase of your life and career.

A few years ago, I was struggling to master a new professional skill that was critical to growing my business. It was hard. At times I doubted whether this ambitious goal would become a reality. I came across Robin Sharma’s “Rules for Being Amazing” and pinned them to the cork board above my desk.

Here are just some of the mantras that gave me strength and helped me keep the faith in the face of obstacles and challenge:

Learn more than normal. Show courage. Breathe. Excel. Adore mastery. Laugh. Cry. Innovate. Aim for genius. Stay humble. Deliver more than is needed. Exude passion. Shatter your limits. Act now. Don’t stop. —Check out the full list.

Whether it be Sharma’s list of powerful intentions or your own grit and determination, keep the faith. The new entrepreneur is a bold and fearless bunch. If you wake up every day on fire, you owe it to yourself to turn those ideas into action. Chase passion with everything you’ve got. When you hit that sweet spot, pressure eases off, work feels more like play. Regardless of whether you’re an entrepreneur, intrapreneur, not-for-profit crusader or community builder, we all have a purpose and you might as well enjoy living yours.

I’d love to hear your tips for living more fully in both work and play!


**All photos taken with my iPhone**