As much as you love your career you have a sneaking suspicion that other aspects of life might be passing you by. Having it all is hard when you work 40 hours plus a week.

Because it’s not just the 40 hours, is it?

It’s the commuting, the running around in between, making an effort to maintain relationships, and trying to keep up appearances, manage your home, & your family (& your waistline). We arrive home, our bodies kidnapped by exhaustion. The exhaustion of life. But sometimes the call of the wild cannot be silenced. Tiredness be damned. There’s an innate curiosity about the world that pinches us from the inside.

Good news: There are a few ways to get out there and experience more of it without jeopardising your career. The following 3 strategies are frameworks only – if they tickle your fancy but aren’t quite right, keep asking ‘how’ until they are.

This is your life. Make it work for you.

1. The Freedom-Seeker Strategy

Register yourself as a sole proprietor and pursue contracts of any length, any time you like.

Ideal for: A seasoned pro or a confident 20-something whose work speaks for itself and loves short-term project work. Highly social people who can integrate fast in any culture or lone wolves.

What you need: Excellent client testimonials and a gleaming track record.

Pros: Work on a project by project basis which keeps life interesting & builds your experience and portfolio quickly. You can establish a name for yourself and high demand for your services fast. In demand during recession while permanent employees are laid off. Write off your expenses.


  • You must be diligent about invoicing & receiving payments.
  • Your salary is gross so you have to factor in the cost of tax.
  • You’re not eligible for company benefits like medical, holiday & sick leave.
  • Demand for your services is performance-based.


  • Build holidays, sick leave & benefits into your rate.
  • Keep 40% of your paid salary in a high interest saving account ready for tax time.
  • Give each contract 120% to guarantee excellent testimonials.

2. The Ultimate Freedom-Seeker Strategy

Position yourself as a consultant when you’re a bonafide expert in your field.

What you need: Proof of high calibre problem-solving skills and innovative thinking.

Ideal for: Those who have achieved guru status in a specific area of expertise and feel confident charging a premium for it. Great for Millennials who master cutting-edge technologies and processes fast.

Pros: Freedom to choose who you work with while charging a premium. You can charge value-based fees for your services because of the high-impact nature of your contracts.


  • Forget about working 9-5. You might work long hours to meet tight deadlines.
  • If your area of expertise is highly specialised it might be months between contracts.
  • Holiday, sick leave and benefits not included.
  • Large checks for the tax man every year.


  • Establish clear rules of engagement during contract negotiations.
  • Budget accordingly: keep 6 months living expenses in easy-access savings.
  • Set aside 40% of earnings for tax purposes and factor benefits into your fee.

3. The-Make-Money-While-You-Sleep Strategy

Transform your expertise into digital products & services that people can buy online from anywhere in the world while you sip margaritas from your hammock.

I know what you’re thinking: I can’t leave my job! Hear me out …

What you need: Entrepreneurial drive and products or services that people want to buy.

Ideal for: Self-starters who love the opportunity & challenge of starting up and being their own CEO. Those who have valuable knowledge or expertise that they can package, or creators & makers who have a product to sell.


  • Complete control over your time and business size & direction. Outsource everything outside of your zone of genius. Breathe life into your ideas and have an impact on the world around you. Complete control over work-life balance over the longer term.
  • You career and your job will ALWAYS BE WAITING FOR YOU if you want to go back. Fact: It looks pretty cool when you have your own business on your CV.


  • Work-life balance is hard at first; fledgling entrepreneurs work 24-7 which quickly becomes a lifestyle.
  • No control over size or timing of commercial success; threat of failure can be paralysing.
  • Startup cash flow can run out fast.


  • Set work-life balance parameters that maintain physical & mental health from the outset.
  • Outsource/ grow your team before you feel.
  • Have a vision larger than this project so you can move beyond failure.
  • An emergency fund to cover six months living expenses; crowd source funding for your project; maintain good relationships within your industry so you have a back-up plan.

Start with the level of risk you’re willing to take and slowly increase it to move closer towards absolute freedom.

Featured image via Pixabay under Creative Commons CC0


Stephanie Holland - Leaders in Heels Guest writerStephanie Holland helps corporate misfits set themselves up for success before they startup. Join the revolution at

When is the right time to give up?


The first 18 months is a wild ride: excitement; challenge; learning; self-development.

Yet when the excitement of starting up wears off and things haven’t turned out as you hoped (or as fast as you hoped) you might find yourself doubting, second-guessing, and questioning your decision to keep going.

18 months is not a long time in the scheme of things. Not really.

But it can feel like a really long time when things don’t go to plan and your sales cart isn’t ka-chinging.

Everything is taking three times as long to make, create, and launch; your cash is running out twice as fast as you projected, and you’re just not feeling it.

Giving up is always an option. Because what have you got to prove?

Nothing. To no one.

This is your thing. Your life. Your idea, after all.

Do it or don’t do it, to paraphrase Yoda.

But things get to be a bit much. Your survival feels compromised and you begin to feel like you’re on the edge.

Do you back away, or take a big leap?

The truth is you’ll get to this point and have to make this decision daily.

Every. Single. Day.

So here are 3 reasons to give up, and 3 reasons not to … for when you get to this point and you really don’t know what to do.

3 Reasons to GIVE UP RIGHT NOW

1. You no longer have any time, energy, or money

You’re running on empty, or dangerously close.

You don’t even know how you’re going to pay rent next month, yet alone pay all your subscriptions (even the bare necessities like web hosting, an online shopping cart, accounting software etc.). Moving in with your parents is an option but do you really want to go there?

You know no longer wake up full of beans but with a deep sense of dread and What the f*ck am I doing?

Free time? What’s that?

2. Your relationship is falling apart

Not just your romantic one; you barely see your friends (frankly they find your constant bemoaning a bit of a drag), and you don’t even like hanging out with yourself any more.

Over it!

3. Your passion has subsided

You jumped in headfirst raring to go, consumed by the excitement of starting up, but you just feel a bit ‘blah’ about it now.

Basically, you’re tired. Exhaustion & passions aren’t great bedfellows, in fact the former is a real mood killer.

You know exactly what I mean.

It means you you get distracted easily, procrastinate like a pro, and avoid the work!

So what’s the point?!

But hang on JUST. ONE. SECOND, you impulsive decision-maker, you …..

3 Reasons to TAKE A LEAP (of faith. Or whatever). Don’t give up!

1. You’re probably on the verge of a breakthrough

The edge indicates close proximity to extraordinary breakthrough.

Life + business can get particularly gnarly when something is about to tip over into amazing-ness.

There’s seems to be neither rhyme nor reason to this other than perhaps to test your commitment at the last hour.

Do you really want this?

I mean: really, REALLY want this?

As you affirm YES! every day, your resolve strengthens and smashes through walls brick by brick, dismantling the barrier and use those same bricks to build the dream.

(Setbacks are opportunities, right?)

The result you’re looking for is right in front of you.

2. You can scale back: go smaller and smarter

So many aspiring entrepreneurs go in TOO big!

Big money, working 24/7, and MASSIVE ideas.

If things aren’t working out how you’d hoped, strip away all the bells and whistles.

Go back to asking the following questions:

What is the essence of your idea? What is it’s core function? Why is it necessary? How is it game changing? What is the smallest iteration of your idea (product or service) that you could sell/ make/ create/ launch right now?

It’s easy to drown yourself in the detail, the features, and embellishments.

Keep in mind: Many of the (best) biggest ideas, projects, products & services start as really simple things:

Google started as and, when it was in the testing phase and was working under the website of Stanford University. Apple started by selling 50 units of Wozniak’s Apple I Computer at $500 apiece to a local retailer. Even Disney started out small, with the filming of the “Alice Comedies” in the garage of Walt Disney’s Uncle.

Even if you don’t want to create a Fortune 500 company (and especially if you do), why would you start bigger than they did?

Really. Why would you do that?

Gauge the temperature of your idea on a smaller scale, before you go BIG (again).

3. You have the chance to be a leader

You were pretty adamant when you started up it was absolutely the right thing to do.

You sold up and shipped out (metaphorically speaking) to follow your dream, despite the protestations of friends and family ranging from: ‘Are you sure’ to: ‘You’re completely insane.’

Many people persist with their ideas simple because they want to be able to say: ‘I told you so.’

(Bad. Bad. Bad.) Wrong angle.

This just needs a little modification. Persisting to demonstrate the possibilities available to us all – in life and business – is a truly noble deed.

When those around see what happens when you go for it, they’ll be inspired to do the same. Maybe one day we’ll have a world full of inspired people. That’s the dream.

And anyway: Get more rest, exercise and relaxation and you’ll be right as rain. But really do that. The right relationships can weather life. Audit yours: are they energising or draining? Passion needs daily activation. Write down your goals and dreams every morning + evening.

Have you felt the pressure to give up? Tell us your best advice in the comments below for other business owners struggling right now?

Photo credit: Vic

Stephanie Holland - Leaders in Heels Guest writerStephanie Holland is a strategist & traveller passionate about living with a wild vision & helping others do the same. She thinks everyone deserves to live with passion, purpose, and vision, and she’s on a mission to empower aspiring entrepreneurs with perspective shifts & strategic frameworks that slice through the bullshit, smash upper limits, and minimise guesswork of self-made entrepreneurship. Grab Your FREE Guide to Validating Your Business Ideas DREAMS So They Make You Insanely Rich.

Naysayers are inevitable.

When are you going to get a real job?

How are you going to make money doing that?

Are you completely mad?!

Hearing these kinds of comments when we already feel challenged can be particularly confronting and force us to question: Exactly what am I doing?!

Things that others say are all too easy to believe when they resonate with what we secretly think might be true.

I mean, how exactly am I going to make a living doing this?!

But don’t despair.

There are a couple of reasons why the naysayers in our life are an important driving force:

1. They give us an opportunity to re-affirm and re-commit to our purpose. Regularly.

It’s all too easy to fall into habit and routine, even when we’ve found our thing.

The drudgery of starting up (admin, operations, endless email) can plunge us into default mode where we’re just chasing our tail. These questions prompt fresh thought about what we’re doing and how to create the business part.

It might even empower us to jump out of business maintenance mode and into business development mode. (That’s the mode where momentum and expansion occur).

Next time someone questions the sustainability and profitability of your idea, use it as an opportunity to focus on the sustainability and profitability of your idea. Sit down and study/ meditate – it might stimulate some fresh thinking around an existing challenge.

2. They give us an opportunity to re-assess our community, decide who we want in it, and how we communicate with them.

A supportive and open-minded community is essential when starting something new. We all need people in our lives who are relatable, and if everyone in our community is still in the same job they’ve had for the last 5 years and think we’re insane for giving up the accoutrements of salaried life while we launch our idea, it’s going to be pretty tough going.

Friends and family love us. But if they are not 110% supportive of our choices and direction, they might not be the best people to share our experience with. Tell them the good stuff so they can focus on the progress you’re making, and save the challenges and request for advice/ feedback with a like-minded community of peers.

To start with, create a list of the 10 people you spend the most time with and tick them if they are 110% supportive of your choices and direction. If not, you can either spend less time with them {at least for the time being}, share only the good stuff or lovingly communicate your greatest WHY and ask for their support in lieu of a gagging order.

You can also spend more time with people who inspire you through their books, podcasts, blogs, webinars and live events. My go-to is an hour with John Demartini on my iPod. It never fails to lift me back up to where I should be.

You might also consider a coach or mentor who can keep you on track and accountable to the goals you set. These are the people who can help you turn your challenges into opportunities (not a reason to give up and go back to what you were doing before).

There are also a couple of reasons why they naysayers in your life can be a creative force:

3. It’s an encouraging prompt to throw ourself into the things that we love that fill us with a vision of the future.

When we do what we love we are happier, healthier, and free-er. And in this state we are more easily able to live in our vision of the future.

Anything to do with personal and professional development are life affirming and invigorating. I always have a professional course on the go (business or marketing stuff), as well as some more esoteric/ holistic stuff and some books that stimulate new ideas. Immersing yourself in study and progress in your passions will advance you in the direction you want to go and quiet the lizard brain that defaults to fear and sabotage.

When the naysayers chime in I fire up the laptop, watch the latest videos in the module I’m up to and very soon again feel passionate and excited about what I’m doing. Because it fills me up with a vision of the future.

This kind stuff gets us back on our path.

4. It’s also a chance to fully immerse ourself in our art; that thing we do.

That thing that you want to share with the world right now? Spend time immersed in the thinking, action or behaviours required to master it, evolve it, take it to the next level. It’s the core of a sustainable, profitable and impactful business.

Whether a product or service, the offer we create around your art is more game-changing and more revolutionary the more time we’ve spent honing, sculpting, and shaping it.

So get stuck in and spend time with that.

Naysayers are a blessing. The curse comes only if we let them side track us.

Featured Photo Credit: Vermin Inc via Compfight cc

Stephanie Holland - Leaders in Heels Guest writerStephanie Holland is a business strategist at, delivering pre-business strategy for more ease, more vision and more likelihood of success. She’s on a mission to empower aspiring entrepreneurs with perspective shifts and strategic frameworks that slice through the bullshit, smash upper limits, and minimise guesswork. Grab a free copy of Plan F to get started generating ideas, impact and profit on your own terms.

When I decided on a frequency for my newsletter #StartupFuel, I didn’t think a fortnight would come around so quickly. But it does (and I kind of love it!).

A week would have sent me over the edge. but it’s not something I dwelled on for too long. My thought process was:

Ooooh a week is too often! Ok, I’ll do it fortnightly.’


A fortnightly delivery schedule made sense because — to be honest — I didn’t know if I’d have enough material to share weekly … but also because it gives me and my subscribers both a chance to live a little in between; to percolate on what I’ve shared and to be wildly happy when they see me in their inbox again. (As opposed to that woman who shows up every week. Good God!)

But it also reminds me that when we’re starting up – whether a new project or business – we have a zillion seemingly tiny decisions to make, and the time it takes to make them can be crazily disproportionate to their importance in the bigger picture.

And questions like ‘Shall I deliver my newsletter weekly or fortnightly?’ can burn a hole right through our brain.

So I want to tell you this:

Don’t sweat the small stuff; don’t get caught up in the detail.

And that’s because one of the core, immutable laws of starting up is: Start before you’re ready.

Because otherwise you may never start.

Did you hear that?

Because otherwise you may never start.

The truth is you can use a number of unimportant excuses to delay launching your business or new projects for months … or even years.

But guess what?

This is procrastination. (Not even undercover, right out there in broad daylight.)

Yeah you’re worried about it not being perfect, but nothing is. Ever.

That’s not because it isn’t (because it probably is), but because even if you had hundred extra hours to think and dwell on the finer details, you still wouldn’t be satisfied.

So you just have to let go.


Launch it into the world so your thing can become what it needs to be to kick some serious game-changing ass.

And once you do you’ll wish you started a year ago.

Here are just a couple of solutions to a few common start-up challenges that might have you running around in circles, delaying the launch of your something most incredible.

#1: I don’t know what to call my new business / project

When my sister was pregnant she thought she wanted to call the baby Maya.

But when baby was born she just didn’t look like a Maya. And it was eight weeks before she grew into her own name: Skye.

The point of this story?

You just never know what name will ‘fit’ with your business or project until you’re up and running.

You’ll get ideas from your customers, from the media, from friends and family. Suddenly everything you watch and read will inspire you; ideas will fly off pages, and you’ll connect dots that have never been connected before.

A neat trick is to start off with your name because building a personal brand is all the rage, and in the future it can double as a hub for your *killer* empire.

#2: My domain name is not available

Simple – choose something else. Hyphenate it. Select a .co instead of a .com

Your domain name is way less important than the tag line.

The tag line needs to be rock solid.

The job of the tagline is to give people an exact idea of how your product or offering can help them, such as:

PooPourri: Spritz the bowl BEFORE-YOU-GO and no one else will ever know!

Barkbox: A monthly box of dog goodies.

Get it by Deesign: Create professional marketing visuals in minutes.

focus@will: Do you like to listen to music while you work?

You see?

None of the domain names make any sense without the tag line.

(And no one really cares about your domain name anyway.)

#3: I can’t afford to have a website developed and designed

Well, you’re in for a treat with this one.

Create your own! You can create a wicked one-page billboard in minutes using About.Me while you work on a cutting- edge one-page website using – also simple silly and easy to build. No design or coding experience required. And both are free, too.

You can nab some incredible royalty-free images from several new creative commons platforms.

To pimp those images or create gorgeous one-of-a-kind graphics you can use PicMonkey or Canva (again, both free), and Nathalie from Pimp Your Visuals will even show you how to use pic-monkey across her four *free* tutorials.

And when you realise how much fun it is you might even want to grab your own Bluehost account, choose an amazing theme from themeforest, and shoot for the stars.

I did all of this – in exactly this order.

And even though I had no idea at the outset, I’m thrilled to announce that I have finally learned a bit of #code. (After a zillion emails to the guy who developed my theme, with whom I’m now twitter friends!

Take some advice from Patajali’s yoga Sutra III-33:

Anything can be understood. With each attempt fresh and spontaneous understanding arises.

I have found this to be irresistibly + deliciously true.

#4: How do I grow my twitter following?

Think of it as an extension of your natural social behaviour and play around a little.

In the last 10 weeks I’ve added 346 to my Twitter account organically simply by:

  1. Complimenting people on their amazing products and services.
  2. Singing the praises of products and services I love.
  3. Tweeting interesting feature articles and adding my own insights.
  4. Re-tweeting other people’s tweets.
  5. Following others! Doh!
  6. Publishing my own insightful quotes.
  7. Publishing pimped up royalty-free photos with my own quotes.
  8. Adding a few hashtags relevant to my category #startup #startupstrategy #impact #marketing.

I’m coming out of the strategist closet myself to earn my own social proof. My top tips?

1: Be human. 2: Be yourself. 3: Have fun.

So back to you.

What are the questions or challenges holding you back from launching something new? We’d love to help answer them in our Comments section below.

Stop procrastinating. Think BIGGER.

How could you start more slowly, more simply?

I’ll bet if you just do it you’ll get all the answers you need.

Image via Raquel Gonzalez

Stephanie Holland - Leaders in Heels Guest writerStephanie Holland is a startup strategist & explorer passionate about living the richest experience of life possible and empowering others to do the same. She runs online classes & one-on-one coaching to help purposeful millennials and corporate misfits create sustainable, profitable & impactful businesses. Sign up for #startupfuel for actionable insights & perspective shifts primed for a digital world, fortnightly direct to your inbox with the four magic words: FREE!