Money & Career

How to be your own boss in just five steps

Life is business, baby, so step up and run it! Read on for our top tips, tools and techniques to turn yourself into a stronger, more effective leader — at work and in life.
By Laura McDonald and Susan Misner
October-2013-Professional-Business-Woman Paul Bradbury/ Getty Images

Boss. Quite the loaded word, isn’t it? Recall the rallying cry of the five-year-old set: You’re not the boss of me! (Exhausted mother’s retort: Oh yes I am!) Of course, it’s not so bad if you’re a guy. Then you’re the boss man...a somewhat kinder, cooler, gentler version of boss, invoking images of frat-style golf tournaments, backslaps and after-work beers. But if you’re a woman, you’re not just the boss – you may be seen as boss-y, an annoying bossypants or worse. Because nice girls don’t want to be in charge. Or at least that’s what we used to think.

For this installment of the Modern Woman’s Guide to Finances, we’ve decided it’s time to “lean in” (thanks for the term, Sheryl Sandberg!) and redefine the label of boss. Of course, we already know you’re brimming with energy and ideas, so let’s focus on how you can step into those boss shoes with power, grace and, above all, respect. Whether you’re climbing the corporate ladder, launching your own business or staking out top-dog turf on the PTA, it’s tough enough to maintain control, let alone successfully manage the whole package. But it gets easier when you remember (and remind yourself) you are in charge. After all, nobody is more qualified to be CEO of your life than you. Here are five golden rules to consider:

1. CEO of "Me Inc."

It’s a well-known fact that no one cares as much about a business as its owner. And guess what, that applies to life too. You’re your own CEO, like it or not, and the secret to things running smoothly is not all that different from leading a successful business. Top CEOs and famous self-help gurus are often closely aligned (think Oprah and Deepak Chopra), because what works best in the boardroom is often an extension of smart personal behaviour: 1) Have a vision. 2) Be committed. 3) Set goals and achieve them. 4) Innovate. 5) Cut your losses. 6) Take responsibility for mistakes (even when you don’t think they’re yours). 7) Build strong relationships and empower others. 8) Reward good performance. 9) Improve communication. 10) Get really good at time management. Hey, we never said it would be easy, did we?


2. Be a boss you wish you had

A recent Time piece named five essential qualities that define a “remarkable boss.” We’ve reinterpreted them here, with our own spin, so you can be a dream boss for yourself and others.

Be generous with your time: There are a million things that keep you busy all day. Yet the most meaningful actions you take as a boss are the ones that force you to step away from the chaos and slow down. Check on a colleague whose mom is in the hospital. Tweet about a great product a supplier just delivered. Buy your work buddy coffee. Meditate. Make time to inspire, reassure and motivate.

Try to bring out the best in people: Your main job is to remove roadblocks that prevent people from doing the job you hired them to do, provide the resources they require and coach them to deliver more than they thought they were capable of. The more you can expand your team’s potential, the more you will all achieve.

Quash problems quickly: When small issues fester, they turn into bigger, uglier problems that distract your team and damage morale. Plus, avoiding issues makes you look weak. Deal with tiny annoyances quickly and decisively so everyone can get back to work.


Strengthen your weakest link: We all have times when we lose our mojo at work. Before the team suffers, work to identify the cause of underperformance or poor behaviour and work one-on-one with that person. This is how you foster talent, build loyalty and create a caring team culture.

Be gracious and humble: When someone on your team accomplishes something great, everyone benefits, including you. Let employees publicly bask in the glory of an achievement and congratulate them for it. Save your own basking for later, ideally in the privacy of your own home.

3. Listen to your gut

If there’s one person who fits our vision of inspirational boss, it’s Sara Blakely. The world’s youngest female self-made billionaire launched Spanx with an initial $5,000 investment and a madcap plan to create some footless tights that she could wear under white pants. So what can we learn from her wild success?


Let setbacks propel you forward: Sara grew up wanting to be a lawyer, but when she scored poorly on the LSAT twice, she reimagined her career.

Don’t quit your day job: Sara worked full-time as a fax machine salesperson while she got Spanx going. Researching patents, visiting hosiery factories and schlepping products to department store buyers were all things she did in her spare time because she still had to earn a living.

Learn things you don’t know: To save money in her start-up, Sara learned how to incorporate a business, register a patent and file for a trademark. She designed her logo and looked after sales, shipping, marketing and PR – on her own.

Get ready for a new set of fears: Once Spanx became a global success, Sara’s life didn’t get easier. She was then faced with confronting her three biggest phobias: fear of flying, heights and being on a stage. All of which she worked hard to conquer.

Embrace mentors from afar: Sara had three key mentors. She was lucky to meet Richard Branson, but all the tools she learned from Oprah Winfrey and Wayne Dyer came from reading their books and watching them speak. (Thanks, YouTube!)



4. Me Inc. in action

Achieving success in your personal and professional lives (corner office, anyone?) comes down to having a “Me Inc.” attitude, says our favourite business expert, Jenifer Bartman, of Jenifer Bartman Business Advisory Services in Manitoba. The Me Inc. approach involves being proactive about growing your skills and experience, rather than waiting for anyone to recognize your abilities. “It’s about making a conscious effort to invest in yourself,” says Jenifer. “If you view yourself as a talent to be developed, you’ll embrace every opportunity as a chance to learn.” Here are just a few of Jenifer’s top tips to put you in position for big boss roles.
Be visible outside your team: Attend seminars, events and training programs your company offers. Even if they happen in other departments, you’ll understand more about your company.
Volunteer: Offer to take on extra projects, organize staff events or pick up the doughnuts. Jump in for the challenging projects and menial work that no one else wants to do.
Get to know your HR team: Ask them about pay ranges and job skills required for the levels ahead of you so you know what to strive for and where you fit in.
Create advisory boards: Look for people from whom you can learn the ropes. Offer to mentor others in more junior roles.
Research your industry: Stay on top of the job market so you have a clear picture of what other firms offer and keep an objective view of your market value. Gain extra industry experience and develop community contacts by putting your skills to work for a non-profit group.
5. How to invest in you
When a public company has extra cash and wants to prove itself a great investment, the company buys back its own shares, essentially signalling the belief that there are no better investments out there for its money than itself. Follow its lead by putting your extra cash where your mouth is. If you work for a company, pay yourself first each month by taking 10 percent off the top of your pay and stashing it in a TFSA or an RRSP.
If you own a small business that doesn’t offer a company pension, it’s critical to save for retirement – and the sooner you start the better. As Sandy Cimoroni, senior vice-president and executive sponsor of the Women Investor Program at TD Wealth Management, says, “Women entrepreneurs face the challenge of growing a business while also working to fulfill personal goals and responsibilities all alone.” She recommends lightening the load by identifying tasks that can be done by an expert, like your personal finances. Professional advice can be instrumental in helping you manage your investments to meet your long- and short-term goals.
Meanwhile, investing in yourself takes on a whole new spin if you hope to one day launch a business. You’ll need to rely on your savings for overhead costs to set up the business as well as help you through initial cash flow hiccups. If you need some inspiration, just think back to Sara Blakely, who turned her entire life savings (a mere $5,000) into the debt-free billion-dollar empire we know and love as Spanx. Not a bad return on investment. hmmm?
Boss women we love!
Besides Spanx creator Sara Blakely, to whom can you look for inspiration? Check out these publicly traded conglomerates, all led by female talent:
Yahoo! (YHOO)
Marissa Mayer became CEO in 2012. She was famously the first pregnant woman to be hired as the CEO of a Fortune 500 company and gave birth just a couple of months into her tenure.
Xerox (XRX)
Ursula Burns is not the first female CEO of Xerox, but she is the first woman to succeed another woman as CEO of a Fortune 500 company (Anne Mulcahy was her predecessor). Burns is also the first black woman to head up a well-known Fortune 500 company.
Indigo Books & Music (IDG)
CEO Heather Reisman is also the visionary who founded the company in 1996. Thanks to her genius, the company merged with its primary competitors — the Chapters and Coles retail chains of bookstores.
Second Cup (SCU)
Stacey Mowbray has been CEO of this Canadian coffee retailer since 2009. Last year, Mowbray served customers on the front line on W Network’s show Undercover Boss Canada.
PepsiCo (PEP)
Indra Nooyi is chair and CEO of the second-largest food and beverage business in the world. Forbes named her one of its World’s 100 Most Powerful Women. She became CEO in 2006.


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