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



Getting Back On Track

Expect the unexpected

This is my first post after a bit of a reprieve. I’ve been sitting here for about 15 minutes, trying to think of what to write. I was 2 minutes away from shutting down the laptop and letting another day (or week) drift by, when it finally occurred to me. That’s what I should be writing about. Because that’s something we can all relate to, right? Trying to get back to some sort of normality, some sense of self, after life unexpectedly side-swipes you and drags you miles off course.

Expect the Unexpected

I loathe the expression ‘expect the unexpected’ because it’s so completely useless. While the intrinsic meaning is well-intentioned, it’s clearly not something that any of us can truly master. We can’t anticipate every possible event and circumstance, nor can we predict with any degree of reasonableness how we’ll react when the unexpected happens. Even if you think you know, you’re probably wrong.

As a solopreneur, it’s incredibly challenging to effectively manage time. Juggling sales, networking, marketing, and professional development, all while trying to ensure customers and clients receive the absolute best that you have to give, can be a recipe for a perfect storm. Keeping all of those balls in the air requires constant vigilance.

Then the unexpected happens.

Something you aren’t prepared for, and couldn’t have prepared for, not in any meaningful way, and you just have to cope.

There’s no magic button, no playbook, no step-by-step script to follow.

Reinventing Normal

I’ve always been a bit hyper-focused on time. Ironic, considering how much of it I seem to waste. One of my favorite things to do, in fact, is nothing. Not only do I enjoy doing nothing, but I excel at it. Lounging in a chair, staring up at the sky, watching the clouds float by. Yet I have so many things that I want to do, so many ideas that I want to test, so many new skills that I want to learn, that I always feel like I never have enough time to do it all. Which of course is true. None of us ever have the time we want, or need. So we prioritize, the best that we can, and more so, we muddle through. We establish our routines, constantly balancing too little time with too many tasks, and invariably end up sacrificing what we truly want on the altar of obligation.

When you experience a loss of someone close to you, I think your mind naturally drifts to thoughts of mortality and the countdown of a running clock. When you’re with someone at the moment of their death, thoughts that were previously abstract concepts, philosophizing best saved for a dreamy summer day, suddenly crystallize into something tangible. As if you could touch time itself.

And when that happens, when time becomes something you can viscerally feel, when it becomes that definitive and finite thing, you start to realize that perhaps watching the clouds float by on a bright sunny day isn’t time wasted at all.

Perhaps getting back on track isn’t about finding a way back to the normal you used to know.  Perhaps it’s about embracing a new normal, whatever that turns out to be.


To Do List Hack Guide – 5 Key Hacks to Make Your To Do List Work For You

To Do List - So. Many. Things.

When you’re a solopreneur, juggling customers and projects effectively is essential to your success. If you’re an aspiring solopreneur, you’re likely trying to juggle a life, a day job, and a side hustle, as you work towards turning your dreams into reality.

If you want to reach your goals, it’s critical that you can keep on track and tick off those To Do list tasks like a ninja.  But all too often the list ends up growing and growing, without nearly enough checkmarks on the ‘completed’ side of the equation.

So how do you wrestle that To Do list to the ground?  These 5 hacks can ensure your To Do list is working for you, as much as you are working on it.

To Do List Hack #1 – Right-Size It

There’s no point having a To Do list which includes items that span days and weeks and months. My anxiety level rises just thinking about this!

A list like that won’t help you focus. If you get overwhelmed just looking at your To Do list, you’re on the wrong path.

Create a Work Inventory

If you need to have a long list of every possible item on your plate, go ahead and create one. But don’t use this as your To Do list. Consider it more of a “work inventory”.

Keeping a written inventory of the work you need to do over the next week or month or even months can be useful, especially if it helps “unload” it from your mind. Writing it down can definitely alleviate those random thoughts that like to swirl around your mind at 3am!

A Work Inventory also gives you a 360 degree view of everything on your plate. You can keep it high-level, and use it to help you keep your goals and objectives in sight, while you work from a more tactical To Do list on a daily basis.

To Do List Hack #2 – Break It Down

But if you want to create a To Do list that actually helps you get things done, it needs to be tactical and focused.

Plan it day-by-day, not weeks and months in the future.

Your To Do list should have the life span of one day. Each item on the list should be items you can accomplish within a day.

But what if one of your To Do items takes days of effort to complete? That’s when you need to break it down into smaller tasks.

Let’s say you have to design a new web site for a customer. Add “Design web site for Customer X” to your Work Inventory, noting when it’s due. But on your To Do list, only write down the individual tasks that will help you get that project done. Maybe you have to meet with the customer to understand their brand, prepare a project plan for the work, get the customer to sign-off on the plan, create wireframes for the customer to review, get the customer to sign-off on the wireframes, draft comps for the customer to review and sign-off, and so on. And depending on the overall size of the project, even these tasks may break down into smaller items.

Basically you want to keep breaking it down until the items that are on your plate can be completed within hours not days.

But Be Realistic – We’re Humans Not Machines

One of the critical factors in being able to plan and manage your work is being brutally realistic about it. Maybe even approaching it with a healthy dose of pessimism.

The world doesn’t allow us to work on anything for a solid 8 hours.

Aside from the very human reality of fatigue, we never get an 8 hour block of time without interruptions. Am I wrong?

When was the last time you could sit (or stand) and work for 8 consecutive hours, without needing to take a call, respond to an email, consume food or water, or take a mental break?

When you inject reality into your To Do List, you have a much greater chance of completing your objectives.

Create Tasks You Can Complete in Two Hours or Less

I love the idea of the Pomodoro technique, but the small blocks of time don’t work well for me. 30 minutes is just long enough for me to get my head in the game, focus, and start to actually produce something. So taking a break after 30 minutes would guarantee that I would never accomplish much of anything.

But, the approach is sound. Work, focused and relentlessly, for a period of time. Then take a short break. Rinse, repeat. How long each period of work should be is a bit of an individual thing. I like 2 hours. After a bit of trial and error, I’ve found that this is what works best for me.

If I work in larger increments before taking a break – say, 3 hours – then I end up getting more fatigued, more prone to distraction, and less inclined to keep plowing ahead after the first two blocks of work. Anything less than 2 hours and it feels like I’m spending as much time taking breaks as I am working! And while that’s a pleasant way to spend the day, it’s not exactly productive.

With 2 hour blocks, and short breaks in between (15-20 minutes), I can accomplish what I need to accomplish without feeling completely drained at the end of the day.

What if you have a task that you know will take about half of your day to complete? Same rule. Break it down, even if it’s an “artificial” partitioning.

What I mean by that is, even if it’s legitimately the smallest parcel of work that you can make it, and it will still take at least half your day, make it into a series. “Begin first draft of final report” becomes one task; and “Complete first draft of final report” becomes the second task.

Why bother with this type of artificial task creation? See above. This allows you to work for a couple of hours; take a short break; then move on to the next item on your list.

It may seem ridiculous to approach it this way, because of course you know that it’s all the same task that you’re working on for those four hours. But it’s amazing how much of a difference it makes mentally to be able to move through your day, crossing tasks off your list every couple of hours.

It keeps you focused, while giving you a consistent sense of accomplishment. It’s that sense of accomplishment that keeps you motivated enough to keep going. Your essentially creating your own positive feedback loop. An essential for a solopreneur!

To Do List Hack #3 – Work The List

This goes hand-in-hand with the above. Let’s say you have 3-4 tasks per day, that you plan to work through. There’s nothing more deflating than jumping to the last item on your list, without having accomplished the other tasks preceding it.

It’s a list that you created less than 24 hours ago, and you can’t even follow your own plan?! Yet we’ve all done it. Changed the game plan on game day because we’re tired, or not motivated, or any other dozen excuses. And that’s what they are, excuses.

But, as noted above, we’re humans, not machines. Reality is, you may wake up, look at your list, and just not be able to convince yourself to jump into task #1 (the one that you thought should definitely be tackled first when you wrote that list the night before!).

If (when) this happens, then don’t just ignore the first few items and jump right into task #4. First, take the time to adjust your list.

Yes, I know, it seems like a waste of time. Because you know that you’re doing the list out of order, and so what does it matter?

It matters. Take the 2 minutes to revise your list. Make task #4 the first task of your day. Then look at the other 2-3 items, and think about what order you want to tackle them. Make those revisions. And then work the list.

Focus on one task a time. Complete the task. Cross it off the list. Take your break. Move on to the next task. Work, accomplish, rest, work, accomplish, rest. Positive feedback loop. Well done!

To Do List Hack #4 – Yes, Use an App

Writing a list on note paper, or post-it notes is wonderfully nostalgic. But not nearly as effective. Do paper notes send you reminders? For that reason alone, go with an app.

Some people like to just use what they have on hand, and send themselves emails or use their Outlook or Google calendar to keep track of their To Do lists. I used to do this.

But ultimately, the emails just became more email clutter and were no more effective than a paper list. The calendar lists were a little more helpful, in that they provided a nice little pop-up reminder, but they just muddied up my calendar far too much.

I’ve since tried a number of different apps, before settling on one that I love (Swipes). There are so many good task managers available, and you should be able to find one that suits you without too much trouble. The key is to keep it as simple as possible. You don’t need a tool that does everything; you need a tool that does this one thing very well.

Task Management App – What To Look For

As I said, keep it as simple as possible. Here are they key things needed to effectively use an app for your To Do list:

  • Quickly create a task and set a reminder for it
  • Easily mark a task as complete, with a tap or a swipe
  • Quickly snooze and shuffle tasks

That about does it. The rest is gravy. There’s nothing wrong with more bells and whistles, as long as you don’t end up spending more time fighting with the tool than using it.

To Do List Hack #5 – Honor Your Commitments

It doesn’t matter what process, organization, approach, technology, or system you put in place if you end up doing any of the following. These bad habits will stop your progress before you even get out of the gate:

  • Not making your list at the end of every day. That’s right, lists don’t generate themselves. It doesn’t matter how busy you are, you can set aside 5 minutes every day to organize yourself for the next day. If you’re reading this and thinking to yourself, “not true, I’m far too busy”, well, then you’re lying to yourself and maybe you need to start working on that first.
  • Not reading your list at the beginning of every day. See above. Lists don’t read themselves. And this is as close to a zero-effort task as you can get. Easily accomplished while getting your morning coffee.
  • Reading your list and immediately blowing off the first item. Revise the list if you must, but don’t succumb to the temptation of ‘winging it’. Work the list, and it will work for you. Helping you to stay on track and get more work done with greater efficiency are the ultimate goals!
  • Ignoring your To Do list completely. If you can somehow manage to stay focused, be amazingly productive, produce the right things in the right order, address all of your priorities, and hit all of your objectives without any kind of task organization, then congratulations! You don’t need a To Do list! But most of us need a little guidance as both a reminder and a kick in ass.

Making a plan and committing to it, even something as small as a To Do list, is an important step in realizing your goals.

At the end of the day, all approaches, processes, tools and strategies must rely on the human factor to make them work.

But as long as you can offer an honest committment to your goals, they can help you achieve them!






Believing These 5 Myths About Solopreneurs Is Holding You Back

It’s one thing to be held back from pursuing your dreams because of some very real risks and a sincere fear of the unknown. It’s another thing altogether to be held back by false assumptions.

How myths start is a topic for another day, but I think a good deal of misinformation is spread, if not created, by those who need to reconcile their own fears with some sort of external validation. And so the narrative changes from, “I’m afraid to do this because”, to “No reasonable person would do this because”. Fools rush in where angels fear to tread.

But that’s just one perspective. Gathering more perspectives can allow you to see something you were missing before.  Everyone has the power to write their own story. And if you’re writing your own story, wouldn’t you want to be the hero?

It’s important to be realistic when considering whether solopreneurship is right for you. Leave your rose-colored glasses on the desk and take a clear look around you.  Just don’t forget that also means having enough perspective to rise above the naysayers and fearmongers.

These are some of the more common ideas about solopreneurship that I’ve heard, but have never really experienced in my career as a solo.

1. Solopreneurs don’t make enough money

Not all solopreneurs fit the ‘starving artist’ category, though some probably do. And of course how much money is “enough” differs by geographic location, personal needs, and lifestyle choices. But that much is true whether you’re self-employed or other-employed.

One thing I know for sure – a salary is an earning cap. Even with an annual increase, and taking into account performance bonuses, there is a set maximum amount of money that you can earn every year.

As a solopreneur, your earning potential isn’t predetermined. As long as you continue to generate value, you continue to make money.

2. Solopreneurs are always desperate for work

Nope. I suppose if you’re perptually lazy and a committed procrastinator, this will indeed become a self-fulfilling prophecy.

But many of the solos that I know end up referring work to trusted colleagues, because they have more than they can handle.

Now, that’s not going to be the case when you first start out. But once you’re established, and if you’re engaged in your business, you can build a customer base and can have consistent work year over year.

3. Solopreneurs go through long stretches of unemeployment

Maybe? I have no idea. For example, in the last 12 years, I’ve had two dry spells. One where I decided to take a couple of months off and just enjoy the summer. The second was self-imposed as well, when I decided to devote all of my energy into building a software startup company. During that time, my solo business took a backseat.

Aside from these two exceptions, I’ve always had consistent streams of income. The volume of that income fluctuated of course; some months are extremely busy, others are a bit leaner. But I’ve always been able to cover my expenses.

4. Solopreneurs are sales and marketing experts

I suppose there are solopreneurs out there who definitely fall into this group, especially those solos who are experienced marketeters who have transitioned into a solo career advising other solos how to market their own businesses.

But for many of us, sales and marketing are parts of the job that were completely new and uncomfortable for us when we launched our solo careers. We learn as we go, and we improve as we grow.

I’m still very much a novice in this area, and I’m constantly looking for learning opportunities and ways to improve my skills. Luckily, customer satisfaction and referrals still count for a lot in business!

5. Solopreneurs are just getting by until they can find a ‘real’ job

None of the solos I know, myself included, would give it up by choice.

Going back to a life spent working for someone else just isn’t a scenario I can even imagine at this point in time. Maybe that will change in the future? But at this point, being a solopreneur isn’t just what I do; it’s who I am.

And that may very well have been the tipping point. When I first started working for myself, for the first few years, I did wonder whether I could continue to make a living like this, or whether I would be better off – safer, more secure – returning to the fold and working for a large corporation.

I never pulled the trigger, because every time it crossed my mind, what inevitably followed was a flood of memories recalling everything that I hated about that world. The amount of conformity required; the micro-management; the politics; the biases; having my work hours dictated by someone else; not having a choice in work assignments; being at the mercy of corporate quarterly targets that I had zero influence on; and the cubicle farms. Rows and columns of tiny gray boxes stuffed with human captives for 8+ hours a day. Ugh.

So as scared as I was of the future, I couldn’t bring myself to return to the past.

And then, as happens, time meandered on. Two years turned into four years which turned into six years. And by the time I hit that 5-6 year mark, I started to realize that I wasn’t just “lucky”. Yes, luck sometimes played a part.  But to be successfully self-employed for that long meant that I was also capable of pulling off this solopreneurship stuff. Imagine my surprise! Introverted, a complete lack of sales skills, no safety net, and yet I was able to find customers and generate income.

I slowly started to realize that I was actually good at my job. And my job was my business. And my business was completely integrated with my life.

Being a solopreneur isn’t my 9-5 job. It’s who I am.

And I wouldn’t have it any other way.


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.


The Best Laid Plans

Ray of lightI’ve previously written about how grateful I was to be able to take the time I needed when my father passed away (Time Stopped But Just For Me). I couldn’t have known then that just three short months later I would be walking that same sad path once again.

Losing both parents in such a short time span is difficult, even as an adult. How little we realize what a day-to-day backdrop our parents provide, as we muddle through our own hectic lives. In their absence, the void is an echo. Life goes on, but the loss reverberates around me.

I’ll get back to my regular blogging schedule soon enough, but not today.

For now, I can offer only these very few, painfully obvious thoughts.

Stop making plans. Don’t wait. Don’t hesitate.

Don’t bank on a tomorrow that may never be.

Life is for the living.  So live!

Life asked Death, ‘Why do people love me but hate you?’

Death responded, ‘Because you are a beautiful lie and I am a painful truth.’

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

And so this is 2016

Now that January is half over, it seems like the right time to take stock and look ahead to 2016. No? Not buying it?  I don’t blame you. The truth of course is that I didn’t have my ducks in a row on January 1st. My ducks were all over the pond, with seemingly little interest in my attempts to corral them.

So while the rest of the blogosphere was diligently sharing their thoughts and perspectives upon ringing in the new year, I was still sipping my wine and contemplating not much more than whether I needed to go out and get more wine.

Life and it’s many surprises pulled at me in November and December, and it wasn’t until the end of that last month when I could even catch my breath and actually return to travelling my path. After I paused for a brief rest.

Two weeks later, I’m slowly regaining my balance and able to consider both the responsibility and the excitement of a being given the opportunity to embrace a minty fresh new year.

It’s been a tough year personally and a great one professionally, which makes for some bittersweet reflection. But then that’s life, isn’t it? Rarely do the stars align perfectly so that all things can be said to be in harmony. It’s why some people fail to even attempt to live the life they truly want. As they continue to wait for that perfect moment, the years continue to roll in and fade away.

I never make New Year’s resolutions, and in keeping with tradition I’ve neglected to make any this year as well. But I love January 1st. The promise it holds, the visceral optimism of a fresh canvas.

Yes, logically, I know that events of the past can bleed into the present and burden the future. We can’t control what the world throws at us. But we have absolute power over how we react.

And while a calendar date rolling over from one day to the next is as ostensibly insignificant as any other twenty-four hour period, taking a few moments to consider a year gone by, while standing on the precipice of another 365 opportunities to make it count, opens your eyes to a vast sea of gratitude.

I’m glad I decided to follow the path I’m on. I’m not a brave person. But I made a few brave choices which have led me to where I am now. And for that, I’m immensely grateful.

Hello 2016. It’s a pleasure to meet you.

The Truth About Positive Thinking


I like to share positive and uplifting articles. It can also be fun to indulge in sarcasm and cynicism from time to time, truly it can, but it’s not productive.

At the same time, I’m not a fan of “anyone can do anything if you just believe it” mentality. Anyone with a bit of experience, whose lived in the world for longer than a minute, can see right through that.

I recently read an article that listed a large number of reasons (25? 32?) why dreaming big dreams leads to success. Dreaming! Leads to success! I didn’t share that article. Because it’s bullshit.

Everyone has big dreams. Everyone. It’s part of being human. Even though the scale of “big” may be relative.

A big dream in America might be to have great wealth, live in a large house, and own several cars. A big dream in Syria may be to live freely, without fear, and have enough food to feed your family.

In either case, dreaming big takes you exactly 0 steps forwarding in achieving those things.

But too many people confuse dreams and wishes with positivity.

Positive thinking isn’t simply believing in what can be; it’s persevering in the face of what is.

Our greatest weakness lies in giving up. The most certain way to succeed is always to try just one more time. ~ Thomas A. Edison