How to Get Back to Business — When You’re A Woman Over 40

Everybody knows I love to be the girl on top—even in business. And yeah, I know, I make it all look so easy. But truth be told, being on top can be a grind and getting there has never been harder. So, it helps to have some pointers along the way which is why I was only to happy to review Nicole Williams’ new book, Girl On Top—Your Guide to Turning Dating Rules into Career Success.

Now for all you naughty minds out there, let me be very clear: we’re talking business. These days, as so many older women struggle to get back into the corporate “game,” they often discover the rules have changed. Girl On Top uses a paradigm most women understand—dating rules—to describe how savvy women get ahead. It covers everything from negotiation tips to drinking with coworkers (all the good, bad, and ugly). It’s the best career guide I’ve read in a long time because of its commonsense, shrewd advice, and funny tough-love approach. Williams is like the friend who cares enough to tell you have lipstick on your front teeth or toilet paper trailing behind you. Plus, she has fashion sense.

Even though most of her advice is applicable to women regardless of age, Williams wrote this book specifically for young professional women. I contacted her by email to ask her questions that might be of more interest to the seasoned professional woman. Here’s what we talked about:

SS (SeasonedSex): When it comes to career, what common attitudes do you see with seasoned professional women than can be obstacles to advancing further?

NW (Nicole Williams): I work with a lot of women (and frankly find myself thinking this too) who feel they have to settle or think, ‘maybe this really is as good as it gets?’ But the way I see is that older professional woman have a frame of reference and an ability to focus and prioritize in a way that allows us to attack a goal wholeheartedly. If you’re going in with your whole heart, I promise you don’t need to settle. The key is to think about “settling” on a few key priorities or goals rather than expecting the world.

Another attitude I see is thinking, ‘it’s too late to risk.’ Whenever I feel like a risk I’m considering in either my personal or professional life is too big to tackle at this stage of my life, I immediately take myself to the end game and remind myself that the biggest risk of all, regardless of age, is regret and wondering ‘what if’.

Finally, there’s the attitude of, ‘I can’t compete with the youngin’s.’ Of course you can! Believe me, I work with a lot of young women who overestimate their talent and believe the world owes them. You can and you should compete. Just don’t pretend to be 25 years old. Accentuate all the experience and wisdom that comes with seeing how things are really done in the real world (…and not on ‘The Hills’).

SS: I’ve talked with many women who’ve have “done what they loved” but the “money didn’t follow.” Now they’re trying to re-enter the work world with a track record of failure behind them. Any advice here?

NW: As an entrepreneur who more often than not is compared to a dog with a bone, before you bail on the business idea, ask yourself if it really has run its course? One of my favorite books is called Many Miles to Go by Brian Tracy. Whenever I think it’s time to throw in the towel, I take another read and decide if it’s really time. These are the three things you need to consider:

a) Is there heat? You came up the with idea for a reason, but is there anyone else who thinks this is something they can use to improve their life?
b) Are you conducting yourself as a business person? (Do you find yourself out of your pajamas and house on more than one occasion a week?)
c) Are you actually out there asking for business? (Yes, you have to market and make the ask – a website doesn’t get hit without some promotion.)

If you’re answering yes to all these questions and are still coming up with nothing, it may in fact be time to step away. But know this, by virtue of even trying, you need to be incredibly proud of yourself. So many people have dreams that they think about and talk about but at the end of the day, they don’t do anything about them. As an employer, I really admire (and will often put on the top of my list), the person who is willing to not only believe in something but also put their time and money behind it. Go back into the world of work with a confidence in knowing you tried, and came away with real tangible take-away learning experiences that will help you to tackle a new job. Entrepreneurship is a really tough and admirable road – nothing to be ashamed of regardless of whether it took off.

SS: MORE magazine ran an article recently regarding strategies for getting back into the market. Some of these involved doing volunteer work (which presumes you can afford that). Others, suggest radically slashing your salary expectations despite your deep experience. What are your thoughts on this approach?

NW: I’m a big believer in the “don’t give away your milk for free”. If you have real talent and experience, one of the critical ways you can differentiate yourself and communicate that you have what it takes as you reenter the market is to be expensive—not cheap. People value what they pay for and I really do believe that devaluing yourself via your salary is a mistake. It may take longer, and it certainly requires confidence, but find the employer who has the pockets to pay you.

SS: Ageism is alive and well. Most of my very accomplished female business friends have removed all dates from their resumes. Any thoughts on handling this?

NW: One of the chapters I most enjoyed writing in my book is the old dating adage, “Don’t Expect to Change Him”. If you encounter an employer who discriminates based upon age, walk away. I know it’s easier said than done, but ageism is one of those things that won’t get any easier on the job – you’re only getting older. You need to work with a company/boss who appreciates all that your age brings to the table and I promise, there are those out there. That said, there are three key fears that employers have relative to age that you need to be cognizant of and work against these stereotypes in the interview:

a) You’re tired: OK so that may be true, but demonstrate real energy and vigor for the job in the interview. State outright you’re willing to put in the long hours (if that’s true) and exert your tremendous effort and experience into the job. Arrive bright eyed and bushy tailed!
b) You’re closed minded: Demonstrate that you have experience but be sure to mention that you love innovation and are not dogmatic when it comes to doing things your way.
c)You’re technically illiterate: Facebook, twitter, iPhone apps–in this day and age, you really do have to have a clue. Sign on, sign up, sign in – you may make some new friends too.

SS: Let’s say you get the job you want, what are suggestions for how an older woman might best interact with what will probably be a much younger group of coworkers?

NW: Forget trying to be twenty again and go for ‘respected peer.’ Nothing looks worse on an older woman than a mini skirt and a contrived, ‘girlfriend, let’s be friends’. Of course you can be hip, but the hippest thing ever is to know who you are–your strengths, abilities, killer legs–and to show them off…in a pencil skirt.

SS: Finally, a more girly question: what’s your frank opinion of gray hair in the workplace?

NW: I have really dark hair and started going gray in my twenties. Personally, while I’m actually expecting to become a “silver fox” someday, that day is definitely not here yet. There is very little that would prevent me from making my standing color appointment every three weeks and you’d never find me without a color-your-gray-stick in my bag. To me it’s not so much an age thing as it is an attention to detail issue.

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