Deborah Lee
Connect with me on social media

Five Tips for an Aspiring Boss Lady

Tips from Deborah Lee: being Boss Lady

If you’re ready to take on the title of Boss Lady of All Business She Doth Involve Herself In, then I have good news for you.

In fact I have great news for you.

There’s never been a better time to cut the cord with your employer and strike out on your own.

In this age of digital marketing and social media, all you need is the ability to be heard over and above the rest. And that can take some time but it’s eminently possible because there’s always room for one more doyenne of the online world. In fact, there’s room for several thousand more, truth be told.

When I set my stall out fourteen years ago to start my own business I did so in absolute certainty that I was done working for someone else.

Rightly or wrongly I believed I could steer my own ship through the choppy waters of commerce and discover my newfound freedom amidst an ocean of opportunities.

I was partly right. I could indeed steer my own ship, but there were a few unexpected hiccups along the way.

If I could pen a list of tips to my slightly naive but ‘keen-as-mustard’ self back in 2004, it would have read something like this…


Expect a Cocktail of Ups and Downs


We all know that life rarely runs smoothly, but when we create and nurture our own business it’s fair to say that we become heavily invested, emotionally and in every other sense.

We know there will be disappointing times, but that doesn’t ease the feeling of crushing upset when they strike. Because, you know, we all like to think we’ll be the one who escapes the net of real life as we skip down the lane to thundering success.

Tip #1: Cry like a baby (if you must) whenever you hit a frustrating blip on your journey, but when the good times roll, make sure you celebrate hard, loud and large. It’s all about balance and perspective, Boss Lady.


Not Everyone is Going to be Thrilled



Don’t get me wrong, most were supportive and excited for me when I formed my new enterprise… But not everyone. And somehow when you’re a woman it can stir their indignation even more.

There were a few rolling eyes and sneering comments when I talked of my plans for world domination, but always from people who I might expected to have acted so.

I rarely have anything to do with said individuals these days. That’s not a complete coincidence.

Tip #2: Whenever anyone tries to knock your dreams to the floor and kick the living fajitas out of them, it’s saying way more about them than you. Practice smiling sweetly, placing your hand gently on top of theirs and uttering “I hope that one day you’re brave enough to follow your heart. I hate seeing you so eaten up with jealousy because I’m unintentionally shining a light on your weakness”. Boss Lady, take your power back.


Don’t Overindulge at the Opportunity Buffet


I’ve already mentioned the F-word.

Freedom means that you’ll be at liberty to pick and choose what you do, when you do it and why.

And the more you explore and investigate what’s available, the more choices you’ll uncover.

Before you know it you could easily end up working for free too often (see an earlier blog post here that I wrote on this), accepting work that’s not in alignment with your skillsets (which inevitably means you’ll feel like you’ve under-delivered) or feeling exhausted and unfulfilled due to your admirable although slightly wonky “I’m new at this and I need all the experience I can get” approach.

Tip #3: Remember why you did this in the first place. Now I’m not saying you should be super-selective to the point of being a prissy little miss, but when you carry yourself with an unequivocal self-assuredness that you’re about quality and not quantity, the demand you’re in will rise together with the calibre of your work. Nobody walks all over Boss Lady.


Embrace the Unexpected Diversion


My first business was in graphic design and photography. I was reasonably OK at both (they had always been hobbies) but I’d never have put myself anywhere close to being at the top of the capability tree in either discipline.

But I enjoyed my work, and I earned a fair living doing it.

Then I discovered social media, and my world changed.

I was a tweeting every chance I had. Every chance.

And then one day, completely out of the blue, I received an email from a start-up saying they’d followed me for some time on Twitter, liked what I’d done for my own business and asking if I’d do the same for theirs.

To say I was excited would have been an understatement, because social media marketing was a closer fit with my previous career in business sales. In other words, it was more aligned to me and my experience.

Tip #4: When something is offered that could take you off in another direction, and excuse me here if I get a bit squishy, you have to listen to your heart. And if that heart’s singing its little cardiac head off, that’s a sign you should probably go for it. This isn’t about saying yes to anything that’s offered (covered in my third point), but it is about making sure you’re tuned into what’s right for you. Boss Lady, be brave.


Own Your Decisions. Then Fall in Love With Them.


I’ve sat wringing my hands in angst over teeny tiny options more times than I care to mention. They were not that important, I see that now… But at the time I thought a wrong move on my part could mean the end of my commercial world. Or my business, at least.

Ironically the really big stuff like “shall we relocate two hundred miles north” was never a problem. I’d instinctively know what was right.

Tip #5: Every choice you make is part of a business journey that will take you to an array of different places to meet countless people. There’s a necessary process to all of this, and your choices will help facilitate that process. But only once you’ve made them, so hurry up already… Be comfortable in knowing that they’re your decisions, and you made them in good faith. The destination they’ll take you to is a place you’ll need to visit, trust me.

Let me just round this off by saying I’ve never regretted deciding to work for myself. It’s exasperating at times, often hilarious and occasionally chaotic… but never boring.

Boss Lady may be crazy, but she’s never boring.

Leave a Comment:

Onalenna Molwelwa says

Great motivation

Add Your Reply

By continuing to use the site, you agree to the use of cookies. more information

The cookie settings on this website are set to "allow cookies" to give you the best browsing experience possible. If you continue to use this website without changing your cookie settings or you click "Accept" below then you are consenting to this.