I Believe In The Dream Chasers

There’s a quote I love from the movie, “The Second Best Exotic Marigold Hotel”:

There are some people into whose laps good things fall.
I am not one of them.
I must go out and get it myself.

So much wisdom in just a few sentences. The first sentence is something that we all know to be true. How often do we look at an acquaintance, friend, colleague, or celebrity and think, “must be nice”.

The second sentence in the above quote, if left unqualified, smells a lot like self-pity.

“I am not one of them”.

If only I had their luck.
If only I didn’t have so many obstacles.
If only my life weren’t so complicated.

But it’s in the last sentence that the seeds of wisdom are planted. “I must go and get it myself”.

Yes. So much yes!

There will always be people who have it easier than you. Just as there are always people who have it harder. But human nature seems to concentrate its focus on the shadier side of the street. It’s so very easy to forget to be grateful for what we have, and focus on what we lack.

Yet gratitude and ambition are not mutually exclusive. Being grateful for today shouldn’t prevent us from striving for something different, something better, tomorrow.

Yes, other people may have it easier. They may get all the lucky breaks. They may be born under that proverbial lucky star. So what? Just because something is hard to do, doesn’t mean it shouldn’t be attempted. At what point might the odds change in your favour? You may never know if you give up the pursuit too soon. Imagine if having given up, you later discover that you were on the verge of catching what you were chasing, around the very next bend.

If you don’t like what you’re doing with your life, the very least you owe yourself is to give your very best effort toward changing it. If not now, when? In your next life?

You may feel like your circumstances in life are patently unfair. But fairness is a misunderstood concept.

“Fairness isn’t equality of fortune. It’s equality of chance.”

Take your chance. Be a dream chaser. You never know what you might catch.

Dream Chaser



We All Dream of Someday


What Does Your Someday Look Like?

Someday. It’s the best day ever.

When are you going to quit that job you hate? Someday.

When will you will start taking better care of yourself? Someday.

When will you start doing what you always dreamed of doing? Someday.

When will you stop putting yourself last? Someday.

Someday is beautiful.

Full of promise, untouched by reality.

Someday is mythical.

It exists in our hopes, our dreams, and even, unfortunately, our best intentions.

One of the inescapable outcomes of suffering a loss is realizing just how ethereal someday is.

Planning for someday is a pleasurable indulgence, but a dangerous addiction. Constantly deferring today’s action to tomorrow’s promise tends to have a predictable and sad outcome. Plans never actioned, dreams never realized.

If I had waited until someday to start my own business, I’d still be working for someone else. I’d still be slaving away to make someone else’s dreams come true.

Sometimes we need some motivation to get started, and sometimes life gives us just the kick in the ass that we need. Other times, we need to find that motivation for ourselves. And the best way to so is to take a hard look at someday. Not just what it is, but when it is.

I’ve touched on this in a previous post (If Time Were Diamonds). Every now and then it’s good to reconcile your someday self with your current self. Take stock. Get real. And nothing is more real than realizing exactly how little time you have to get from here to there.

Don’t stop dreaming, and hoping, and planning. But stop waiting. Start doing. What do you want? Figure that out first. Sure, it could change in five years, but as of this moment in time, what do you want?

Now go get it.


Why A Lifestyle Business is Better than a Startup

Lifestyle-Startup InfographicStartups get all the glamour, especially these days. Even the language of the startup scene is sexy. VCs, Angels, incubators, acquisitions and exits. Exciting!

But that’s only some of the story. What about stress, sleeplessness, failure, debt, dependency, despair. Hmm. Less sexy.

So what is a lifestyle business? It’s the definition and epitome of professional independence. A lifestyle business is a business that you build on your own terms, which allows you to earn money while living your life.

How do I know it’s better to start a lifestyle business than a startup? Because I’ve done both. The startup is long since dead. And the lifestyle business is still going strong (12 years later)!

There’s nothing like experiencing both sides of the fence to help you see the light, and without any future ‘grass-is-greener’ pondering to keep you awake at night.

It’s all about the end game.

Yes, a startup holds the promise of reaching epic levels of financial reward that most of us can’t even imagine. But the chances of getting there are infinitely small. And the price you pay for just the slimmest chance to play is huge. You give up all of your free time, all of your money, most of your relationships, and some of your sanity for as long as it takes to reach that goal, or more commonly, for as long as it takes to fall into the abyss. Then you get to ‘enjoy’ the challenge of climbing out, on your own, with nothing and no one to help you and no safety net in place if you happen to stumble again.

With a lifestyle business, you’re highly unlikely to become a member of the billionaire club. But you risk little to nothing for a reasonable shot at creating a comfortable lifestyle for yourself, while still living your life, enjoying your friends and family, getting a good night’s sleep, and answering to no one. Think about that. Answering to no one. Imagine not having to ask permission to take a day off. Imagine not having to ask permission to work different hours just because you feel like it. Imagine being able to work from the beach. Or the park. Or the coffee shop. Whenever the hell you want. Without worrying about bosses, or employees.

Lifestyle business vs Startup. What is the life that you truly dream of living?


5 First Steps to Becoming a Solopreneur

SolopreneurWell here we are. That time of year when, for many, the bright glow of optimism and resolutions is dimmed by the reality of the day-to-day grind. But isn’t your desire to escape that day-to-day grind at least part of what fueled those resolutions in the first place?

Don’t be a slave to the calendar. If you resolved that this will be the year that you finally escape from the 9-to-5 monotony, and start working on your own dreams rather than busting your ass for someone else, you still have more than 11 months to make that a reality. That’s plenty of time to get some traction.

Break it down into actionable steps

Looking at the whole picture of what you want to accomplish can be intimidating. That’s why it’s important to break it down into steps.

Keep it practical, and simple. Start with defining what you are as a solopreneur. For example, I’m a project management solopreneur. I offer a buffet of services and products under that umbrella, but that’s the heart of what I am. It doesn’t matter whether I’m working with a client as a project management coach, or assisting a client with some of the more technical aspects of scheduling and managing their projects, my business revolves around project management. The reason for this is simple – knowledge, skill, and experience in that subject matter. I have plenty of all three, and I like the work that I do, so it was an easy leap for me to develop my business along this path. What about you? What are you good at? What do you love? What do have experience with?

Sometimes the answers to those questions don’t align the way you wish that they would. Maybe you have the passion and the aptitude, but lack the experience. Maybe you have the experience and the skill, but lack the passion. This is where you need to dig a little deeper. If you’re going to make the transition from employee to solopreneur, you’ll want to follow your passion. But maybe you need to start selling what you know, while you’re gaining more experience in what you love. A journey isn’t accomplished in a single step.

Begin before you’re ready

This is the one that holds most people back. The never-ending wait for that perfect moment. And it is absolutely never-ending. Some people are waiting “for the right time”. But does such a moment actually exist? If you’re waiting until you have 6 or 8 or 12 months of living expenses saved before you spectacularly quit your job and start your own business, then invariably the day after that moment crystalizes, some unforeseen event will occur which changes your situation or your budget. Life is riddled with surprises. You can’t plan for all of them. Waiting doesn’t guarantee success. It just runs the clock.

Why wait at all? Why not start your solopreneur path now, while you still have a day job and a steady income? Yes, it is absolutely more difficult to try and squeeze extra time out of your already busy days. But if it’s important to you, and if it can be a life-changing experience (yes!), then isn’t it worth sacrificing a few hours of television every week to work on your dream?

Once you’ve made the decision to turn your dream into reality, you’ll also need to avoid getting bogged down in the weeds that will undoubtedly surround you. You can’t write a perfect business plan, create the perfect website, have the perfect Facebook page, and perfectly hit all of your sales targets, all at the same time. You need to do the best you can, adapt as you go, and keep moving forward. Understand your business goals, create a simple landing page, let your social networks know about your exciting new business, and then focus everything you have on making sales and delivering value.

Make your first sale

The best time to make your first sale as a solopreneur is when you already have an income from another job. It means working evenings, working weekends, and agressively managing your time. But this is your dream, and your life-changing plan that you’re working on, so that won’t be a problem.

It’s one thing to lie to your friends, but don’t lie to yourself. Not every failure is due to “not having enough time”. If you can’t make a sale now, what makes you think you can make a sale after you quit your day job? And remember, all sales count. It doesn’t matter whether your first customer is a friend, a colleague, or even your current employer (though I’ve only seen this happen in very few situations).

A paying customer is a paying customer. It’s a critical first step to validating your business idea. And making a sale, securing income, for a business that you own and that you started and that you’re delivering all by yourself? It’s an indescribable feeling.

Keep up the momentum

Have you ever heard that expression, that it’s easier to find a job when you have a job? Sales aren’t dissimilar. That’s one of the reasons that making your first sale is so critical. Sales lead to other sales. As long as you capitalize on the moment, and nurture them correctly.

Customer feedback, word of mouth, marketing your existing sales to gain more sales all help your business develop and grow. Take on as much work as you can handle. “As much as you can handle” means as much as you can confidently deliver successfully, even if it means overloading your schedule for a period of time.

Monitor, measure and move

There’s no point to putting in the work unless you have the courage to reap the reward. This means that once you’ve made a few sales and have some momentum, that’s the point in time when you have to make the hard decisions. Is now the time to leave your job and devote all of your time to your business? Can you continue to do double duty, and perform well at both your day job and your solopreneur side business, for a little bit longer?

Once again, you need to be completely honest with yourself. The reality is that it’s highly unlikely (though not impossible) that you’ll earn enough business income on the side, in those evening and weekend hours, to actually match or surpass your regular paycheck. In a perfect world, yes, this is what would happen. You would continue to work on your side business until its earnings were the equivalent of 120%-150% of your paycheck. Then you would quit your day job, reclaim all that extra time, and not miss a beat in the income department. But now we’re back to waiting for perfection, and other things that never happen.

So, no, you likely won’t replace your day job income by working on your solopreneur business evenings and weekends. And no, it’s not reasonable to think that you can work 12-14 hours a day, every day, for a lengthy period of time without completing burning out. And that’s a hard way for a dream to die.

The question is whether you have sufficient success with your side business that the time is now right to go all in. Evaluate your performance with a critical eye, but don’t succumb to pessimism and cynicism. It’s important to be honest and objective. Reviewing performance and trying to project future sales is a risk-based game that every solopreneur, freelancer, and self-employed person needs to play.

Look at your performance in terms of percentages. What is your percentage growth over the period you’re reviewing? What percentage of your time did you spend on making those sales and delivering those results? What capacity constraints do you have now? How will this change if you quit your day job? How many months and how much money will you burn before your business income will confidently cover all of your expences? These are numbers that can help you make informed decisions and mitigate your risk. They’re also numbers you’ll never have until you make that first sale.

One last question to consider. What will you be doing on January 1st, 2017?

Will you be making the same resolutions as this year, hoping once again to start working on your dream?

Or will you be toasting your own success and reflecting in wonder on what an amazing and life-changing year it’s been?

“How did it get so late so soon?” ~ Dr. Seuss

The Value of Being Authentic In Business

Authenticity When The Focus Is On YouStarting your own business, or becoming a solopreneur or freelancer, isn’t unique. Thousands of people embark on this journey every day. Some succeed, and some fail. It’s this possibility of failure that holds so many people back from pursuing their dreams. And it’s the mystery of success that holds back others.

Dreams and Ideas

People like guarantees. But when you have your own business, certainty is a luxury. Competition is tough, and always will be. Even if you come up with an idea that no else has, a first of its kind, whether an idea for a new product or a new service, it’s ephemeral. If you do nothing with your idea, you’ll wake up one day, weeks or months later, to read about it being launched by someone else on the other side of the world. If you move forward and action it, and start your own business around this one killer idea, you’ll wake up weeks or months later to discover a dozen competitors have sprouted up around you, seemingly out of thin air.

Anyone can have a great idea. Many people have great ideas every week. Successful business are never about the idea, and always about the execution. Before Facebook, there was MySpace. Before Google, there was Yahoo.

Execution and Outcomes

The thing about execution, is that it resonates on so many levels. Product, marketing, sales, engagement, delivery, strategic, tactical. There’s no single magic combination of elements that consistently produces a sucessful outcome. What works for one business or industry doesn’t work for another. That’s the risk that every entrepreneur and solopreneur takes on a daily basis.

Yet there exists a whisper of commonality that gives rise to a certain flavor of ‘survivalism’ among our ilk. And it has nothing to do with stockpiling food and living “off the grid”.

A Single Thread

Whether you’re an entrepreneur running a funded start-up company or a solopreneur paying your bills with income created from your own business, you are the beating heart of your company. You determine the paths taken, the values adhered to, and the boundaries respected. You decide how far you’re willing to go for success. For profit. You decide how far is too far, or not far enough.

In a global marketplace of tough competition, it’s all too easy to crack beneath the overbearing pressure. To imitate your competition, rather than admire them. To follow the trends, rather than define them.

Don’t be a poor imitation of someone else’s value proposition.

Being authentic is not determinant of success for a business. Indeed, in some circumstances, it may mean choosing failure rather than compromising too much, too far, too deep. Choosing to be authentic means refusing to be something you’re not.

So, yes, authentic businesses fail.

But authentic founders are strong. They’ve had their strength tested, and persevered.

They move forward, knowing there’s never a need to look back.

They look straight ahead, knowing they have no reason to look down.

They are the survivalists in a world of change and uncertainty.


Making The Switch From Employee to Solopreneur, Part 4

You have to get along to go along. A familiar expression, often quoted, the meaning of which is clear. Best not to cause waves.  Smooth water, smooth sailing, right?

After you’ve made the switch from being an employee to self-employment, this concept will dominate your thoughts more frequently than you could ever imagine.

What Are the Rules When You’re Self-Employed?

Knowing when to compromise, and when not to, is a delicate balance when you’re trying to establish yourself and your new business. The goal is to build a loyal customer base, and grow relationships. The last thing you want to do as a self-employed individual is burn every bridge you walk over.

And make no mistake. The pressure to make money – to generate your own income – is enormous now that you’ve left the world of pay-checks behind. If you can’t find a way to make money, you can’t pay your bills. The math never changes.

So yes, there will be customers and projects that demand more than you’d prefer to give. And yet you do. There will be customers and projects that you regret ever taking on. And yet you have.

But there are boundaries.

There must be boundaries, for without them, what remains?  You’re a solopreneur. A business of one, but still a business.  Self-employment does not equal servitude.  You’re not a servant-for-hire. You have boundaries.

And the customer is not always right. In fact, sometimes the customer is so wrong, so very, very wrong, that you may have a professional obligation to protect them from themselves. If you’re a service provider, like I am, then customers purchase not just your services, but your expertise.

They’re engaging you because you offer a skill set that they don’t have, experience that they haven’t acquired, training that they need to leverage. It’s your duty to provide them with the best of those abilities. That’s your value proposition.

Invariably, you may find yourself in a situation where your customer insists on taking a course of action that you know will result in a poor outcome for them. What do you do? Shut your mouth, do what they want, take the money and run? Or use your expertise to guide them in another direction? What if they insist? What if the choice is do as I say, or don’t get paid?

Never forget who and what you are. You embarked on this journey for a reason. Did you give up being an employee who answered to a manager just to be a servant who answers to yet another master?

People will mistakenly assume that now that you’re in business for yourself, you’ll take on any job because you ‘need the money’. Even if you don’t need the money, they’ll assume you do. And if you do need the money, the worst thing you can do is reinforce the belief that you’ll do anything for it.

While your building up a customer list and growing your professional network, you’re also establishing your reputation. Saying yes to work you should say no to, or allowing a customer to suffer poor outcomes that you could have prevented, do nothing but provide short-term solutions when what you want is a long-term strategy.

Don’t allow yourself to be nothing more than a commodity.



Making The Switch From Employee to Solopreneur, Part 3

I don’t consider myself a particularly rebellious person. I cross the street when the light says “walk”. I stop at red lights even though it’s the middle of the night and the streets are empty. I don’t park in ’no parking’ areas (unless it’s cheaper to pay the parking ticket than it is to pay for suitable parking). I don’t spend all of my energy raging against ‘the system’.

But I am infinitely curious. And I as much as I’ve tried, I can’t stop myself from continually asking the question “why”. I realized very early on in my career that this is not a character trait that bosses or corporate executives welcome.

“All employess shall follow the dress code”. Why? Can’t they be trusted to dress appropriately for their circumstances without needing to follow a ‘code’? Do employees need to be indistnguishable in order to be effective?

“Employees are not permitted to work from home”. Why? Because if they’re working from home, how do you know they’re working? How do you know they’re not? How do you know if they’re working while they’re at the office? Are they monitored every minute of every day? Presumably they need to produce results. If those results are produced, does it matter from where?

Why do organizations create so many rules geared towards dictating the behaviour of employees? Is it because there are always a few people who make poor decisions, and organizations don’t have the courage to deal with those people directly so they make blanket rules to save themselves from having awkward conversations? Could it really be sometime as simple as cowardice?

For some of us, myself included, transitioning to self-employment is like finally finding your way home. It just “fits” better than the master-servant world, with it’s rigidity, rules and expectations. Where trust is an anthem that never manifests.

Nevertheless, freeing yourself from that world isn’t as simple as flipping a switch. Through your employment years, you’ve become indoctrinated with the rules and regulations of the corporate world. One of your first goals as a solopreneur is to shed those chains, and break free. The longer you’ve been an employee, the more you’ll need to unlearn.

Unlearn: 8 Hour Days

When you work for yourself, you don’t have an eight hour work day. Some days will be 12 hours. Some days will be 3 hours. Trying to sculpt this into a more predictable pattern is a losing battle. You’ll need to be flexible. For some, this flexibility will be jarring. But there are two sides to every coin. You need to be flexible, in order to meet the demands of your clients and customers. But you also get to be flexible, and enjoy the benefits of a more integrated work-life schedule. You’re no longer obligated to work from 9am to 5pm. You may find yourself working from 8am until 1pm, then spending your afternoon at the beach or the golf course or gardening or working on the next best seller, and then working again from 6pm to 10pm.  And the next day, your schedule may be completely different. Be disciplined, but enjoy the flexibility.

You are not an employee.

Unlearn: Waiting for Direction

Your days are no longer dictated by direction from those above you in the food chain. There is no one above you. You may have clients and customers that you interact with, but it is not their job to manage you, nor is it your job to “report to” them. Be proactive. Take the initiative, and ensure that you’re continually driving things forward. Don’t sit and wait for a client to get back to you. Follow-up, clarify, communicate. You’ll make mistakes. Own them, learn from them, and move on. Always forward.

You are not an employee.

Unlearn: Validating Your Decisions

You and you alone are responsible for your business, and the decisions you make. You’ll neeed to make decisions constantly, every day. Be thoughtful, but don’t let yourself get dragged down by ‘analysis paralysis’. Overthinking, stalling, second guessing yourself, and deferring decisions will cost you more time, money, and opportunity than a bad decision. You will not always have all of the information you want before executing. Decide, take action, and then manage the outcomes of that decision, whatever they may be.

You are not an employee.

Unlearn: Working Hard

First of all, let’s get this out of the way: yes, of course, working for yourself is hard work. But don’t use “hard work” as the solution to every problem.

If a customer demands more than you have agreed to, or is looking for you to meet a deadline that you know isn’t reasonable, don’t delude yourself into thinking that you can “work hard” and get it done. Nor that you should just work hard and get it done. In most cases, you’re setting yourself up for failure. Even worse, you may succeed, resulting in raised expectations, more demands, and an unsustainable cycle that leads you straight to burn out. As a solopreneur, no one is going to intercede on your behalf, or protect your interests. Ever. You need to protect your own interests, and sometimes this means saying no, setting boundaries, and managing difficult conversations. Sometimes it can even mean ‘firing’ your client.

You are not an employee.

Unlearn: Putting Yourself Last

Employess are used to waiting their turn. Some patiently, some resentfully. They’re trained to have lowered expectations. Not enough money this year for professional development? Wait until next year. Not enough money this year for bonuses (for everyone)? Wait until next year. Overdue for a promotion but no career path available? Wait until it’s your turn.

As a solopreneur, you’re only competing with yourself. Make sure you develop your skills, manage your career, and explore new challenges. It’s all too easy to become completely consumed by the demands of customers and clients. It’s important to carve out at least a little bit of time to invest in yourself. It will make you a better professional, which will be reflected in the engagement and enthusiasm that you bring to your daily work.

Just like an employee.



Making The Switch From Employee to Solopreneur, Part 2

One of the first challenges you’ll face when you decide to work for yourself is coming to terms with the realization that you are now truly on your own.

Your days are no longer structured. You don’t have a boss or a manager. You don’t need to submit a vacation request or get a doctor’s note because you’re sick. You don’t have to ask permission to wrap up work early. Freedom!

You’ve also separated yourself from the crowd. Unless you’re running with a particularly entrepreneurial group of friends, there’s a good chance that most everyone you know is an employee who works for someone else. They have a day job. And you, now, do not.

What Your Friends Will Think When You Quit Your Job

Most everyone will think that you’re crazy. Basically. Or in need of some serious counselling. Or “going through a phase” that undoubtedly will and should pass in due time, and gee, they sure do hope you don’t ruin your life in the meantime.

In some respects, they’re not entirely wrong. It does seem a little crazy to give up a situation where you are guaranteed to receive money every two weeks just as long as you show up and do a good job. Hell, some jobs just require that you show up and not offend anyone. It’s a fairly simple formula really.

So why would anyone reject that? Why say no to a sure thing? Why become a solopreneur at all? Well you already know why. The frustration of being constrained by someone else’s rules and priorities, the desire to be your best self, the need to have an impact, the fear of becoming a mindless drone, the dismay of every day being the same as the last.  And, freedom!

The problem is, your friends and family won’t see it that way. They may not experience the same hopes, fears, desires that you do. Or they may, but they lack the courage to act on them and can’t understand how you could possibly do so. Not that they would admit this to themselves. That’s not how fear works.

Change is different. Different is scary. Scary is wrong. Different must be wrong. Change must be wrong. What if you fail? What if you don’t? What does that mean for them?

What You Will Know That They Don’t Know

Every fear and negative belief that has stood in the way of your friends’ secret, unacknowledged dreams will be thrown at you as definitive proof that you’re crazy.

Sometimes it will be wrapped in the trappings of proffered wisdom and passive aggressive condescension. “You’re planning to start your own business?” “I’ve seen statistics on how many small businesses fail, it’s pretty scary, how do you know yours will succeed?”. The implication of course is that you are uninformed and unwise and impulsive, otherwise you wouldn’t consider such a crazy idea.

Luckily for you, your wise friend who has never had the courage to make the leap that you’ve just made, and has zero experience with what you’re about to do, can guide you back to the safe and sure path of biweekly pay-checks. Right. So you can be just like them. Because different is wrong.

But you have a secret weapon.  You know what they have yet to discover. What they may never discover.

You know that you’re not 100% sure that you’ll succeed, because no one can ever be 100% sure of a future that has yet to reveal itself. But they too can’t really be 100% sure that their job will still exist five years from now.

You know that you don’t need guarantees, because you’re willing to face things as they come, and take on each obstacle at a time. You don’t need a boss or a manager to tell you how to do that or make those decisions for you.

You know that you’re passion and positivity will fuel you, and your work ethic and commitment will buoy you. You don’t need someone to tell you when to show up to get the job done.

You know that one failure doesn’t end you. It doesn’t define you. It gives you the resolve to do better next time. Because there will always be a next time.

And most importantly, you know that no one ever makes their dreams come true by not even daring to try.

What You Will Do That They Will Never Do

As much as we all want the people in our lives to support our dreams, sometimes they just can’t. That doesn’t mean that you should give up. People fear what they don’t understand. They envy that which they don’t believe they can ever have. And they disparage that which they envy.

These are observations, of course, not absolutes. But the point is to look beneath the surface. Consider some of the motivators before you accept your friends’ criticism as truth. Because the only truth you’ll find there is evidence of their fears and what’s been holding them back.

At the end of the day, the only person that needs to believe in your chosen path is you. Because the only person walking that path is you.


Making The Switch From Employee to Solopreneur, Part 1

By far, the most frequent questions asked of me, professionally, have to do with making the switch from employee to solopreneur. Or from employee to contractor, or freelancer, or entrepreneur, or self-employed, and so on. Whatever your perspective. It transcends demographics, industries, skills, and experience levels. People at every age and stage of their life, in a variety of careers, are inquiring about leaving the world of employment to strike out on their own.

In fact, I know so many people who are thinking of making the switch from employee to solopreneur, or independent contractor, or freelancer, that I often think the world of employment is on the brink of being decimated by mass resignations of the workforce any day now.

Of course, that’s not even close to reality. For a couple of reasons.

Employees – No Longer First Choice?

First, corporations aren’t desperately seeking to hold onto their employees these days. In fact, the trend is just the opposite. Organizations are looking for contractors and freelancers more often as a means to get the job done. (Intuit 2020 Report: 20 Trends That Will Shape The Next Decade) The world economy continues to shift more toward a “gig” economy, where resources are hired to deliver tasks and projects, rather than hired to fulfill the role of “employee of company x”. In many situations, this is a less expensive option for organizations, even though contractor rates on the surface seem high in comparison to employee salaries. But beneath the surface, it’s the associated expenses related to staffing employees that drive companies to engage “per project” resources more frequently. Employee benefits, paid time off, sick leave, overtime pay, on-boarding investment, professional development and training costs, off-boarding investment, and more add significant bloat to the salary line item. With contractors and freelancers, what you see is what you get. Work is estimated, budgeted, contracted, delivered, and paid for. The end.

The Courage to Change

Second, of the many people who are thinking of making the switch from employee to solopreneur, most will fail to pull the trigger. It’s not so much that they’ll fail at their attempt, it’s that they won’t even try. A small tragedy, really, for those who have the desire and likely the capability, but simply lack the courage to realize their dreams. On the other hand, for those of us who pulled the trigger years ago and make our day-to-day living as solopreneurs or contractors, we needn’t ever really worry about a flooded market. There will always be just enough fear to hold back just enough people.

At the same time, a few will certainly dare to take the leap, and so I’ve decided that the next few posts are for them. Or for you, if you count yourself among them. There are all kinds of “how to” and “tips and tricks” posts out there on the interwebs which can give some great tactical examples of steps to take to make this transition. For my part, I’d like to focus on sharing some thoughts and experiences about what it’s really like to live without a pay-check. Because all of those people who are to afraid to pull the trigger? Well, they have a point. It’s terrifying.



How To Manage Yourself

As an employee, you report to someone. Doesn’t matter what your title is, or where you are in the corporate hierarchy, everyone reports to someone. Even the CEO. Up through the food chain, each link is accountable for their actions and must account for them to the links above.


When you work for yourself, who are you accountable to? Your customers? Not really. At least, not in the same way. Self-employed people are accountable to themselves.

If you’re self-employed like me, you develop your own business strategies, and then are solely responsible to execute them. You alone determine your business goals, sales targets, marketing plans, and deadlines for achieving results.

So how do you hold yourself accountable? How do you motivate yourself to get those results?


The biggest motivator, of course, is failure. Or, failure avoidance. It’s an even bigger motivator than the concept of “success”. Success can be such a broad concept, so intangible in tactical application, that it begins to lose meaning. It becomes the elusive pot of gold at the end of a rainbow you’re always chasing.

But avoiding failure? That’s real. That’s tangible. Not being able to pay your bills every month is a failure. Generating income avoids that failure. Being able to pay your bills every month is very motivating! It’s also very urgent. It’s top of mind. Most people aren’t able to ignore finanical obligations and not think about them for months on end. You’re less likely to procrastinate when you know that doing so will have very tangible, and potentially catastrophic, results.


The fact that not generating an income results in a failure to pay your bills may be motivating, but it doesn’t automatically empower you with the ability to create money from thin air. It does put a lot of pressure on you, and potentially create a never-ending stressful lifestyle. If you allow it to.

This is where you need to provide yourself with the support you need to get the job done. Again, another responsibility for you, the solopreneur, because you’re doing this on your own. If you’re wondering why at the moment, take a few minutes to remind yourself why it’s better to be self-employed.

Continue reading for some quick tips on how to provide yourself with the necessary support to stay motivated, accountable, and delivering results.

Top 5 Tips To Managing Yourself

1. Once a month, set aside 3 hours to review your business plan (yes, you should have one!). Confirm or modify your plan as needed.

2. Every three weeks, review your CRM and note which key contacts you haven’t connected with recently. Identify 4-5 contacts and reach out to them to re-connect. Businesses are fuelled by relationships. And if you’re only reaching out to people when you need to make a sale, you’ll find that people will soon stop taking your calls. Reach out to your contacts to keep in touch and see what they need. Helping others also helps yourself, in the long run. And yes, you should be using a CRM system. There are many free or cheap options available for small business.

3. Every two weeks, set aside 1 hour to update and reconcile your budget vs your actuals, both your personal budget and your business. Yes, you should have your budget written down and be tracking what you make and what you spend. Never go more than 2 weeks without reconciling.

4. Every week, set aside 2 hours to review how many of your objectives and obligations you successfully met; how many did you fail to meet; and what are the outcomes from failing to meet those objectives. Did it matter? What did it cost you?

5. Every day, take 15 minutes to setup the top 3 goals that you need to accomplish. Use whatever task or ‘to do’ system or app that works best for you. Make your 3 goals bite-sized; they may be small individual accomplishments, or they may be steps to achieving a larger objective. For example, if your goal is to write a book in 90 days, then a daily goal may be “write for one hour”, or “write 1000 words”.


Be focused on what you’re trying to achieve, both long-term and short-term. Be ultra-aware of your financial position, always. Stay connected to past customers and potential customers. Focus on delivering results every day, both for your customers and for your own business goals. Don’t just plan, analyze. Review actual outcomes, continually, to measure and monitor your likelihood of meeting future goals.

Manage yourself proactively. You aren’t just central to the success of your business, you ARE its success.