5 First Steps to Becoming Self-Employed

Self-employed home office

Many people dream about being self-employed and making money on their own terms. No more bosses, no more bullshit. But you can dream all day, and that won’t change your circumstances. The only one who can change your circumstances is you. It doesn’t need to be drastic or dramatic. Drama is best saved for the world of entertainment, not your professional career.  So you want to be your own boss? Let’s action that.

Start Small

I find people have pre-conceived notions of what “starting a business” means. Generally it’s whatever they’ve been fed in their daily diets of tech blogs and silicon valley success stories.

But there’s a big broad world of microcosms beyond those boundaries. Small businesses strive and thrive everywhere. With digital mediums and online marketing providing a lower cost of entry than ever before, people everywhere are making money for themselves.

If you’re an employee looking to step off the treadmill, do so at a reasonable pace. You don’t need to build the next Google. Don’t let yourself be intimidated by the thought of renting office space, hiring employees, investing huge quantities of money just to ‘test’ whether your idea will work.

Start with what you can accomplish without a huge investment. Want to start a catering business? Cater a few small events initially for friends/acquaintances. Want to start an online business? Create a website and start actioning your plan for an hour or two each day, after your day job. Figure out what works and what doesn’t when the stakes are small.

Start With What You Know

Making money isn’t magic, and it isn’t dumb luck. It’s about generating value. People who don’t know what you know will pay you for that knowledge. And people who can’t do what you can do will pay you for that ability. Whether it’s a service (‘I don’t know how to do X, but you know how to do X, so I will pay you to do X for me’) or a product (‘I can’t create Y, and you’ve already created Y, so I will pay you for Y’).

Everybody has knowledge about something. Everybody has skills. What do you know? What can you do? It doesn’t have to be unique. You don’t need to be the only one in the world with this talent. But it needs to be comprehensive. Comprehensive knowledge or skills means you can compete.

Start Now

People that talk to me about wanting to work for themselves, people who dream of being self-employed, consistently express one common theme – “when the time is right”.

Often, for those dreamers, the time is only right when it’s easy (‘I have $100,000 in the bank and nothing to spend it on, what a great time to be self-employed!) or when it’s necessary (‘If I ever lost my job, I’d become self-employed’). “Easy” will never happen; “necessary” happens all too often.

The problem with waiting until you lose your job before you start your own business is that you’re starting at step 0 at a time when you have 0 income. Not smart.

Whenever you start, you will not be an overnight success. This doesn’t happen. Depending on your business, there’s a better than average chance that you also won’t be successful in one month, or two months, and possibly not even in six months.

Starting your business in your own time, while you still have a day job, is the safest, least risky path to successful self-employed.  That wasn’t my path.  My hand was forced, and I had to react, and react quickly.  Vistria’s origin story was more big bang than slow burn.

While the pressure of not knowing whether you’ll be living on the street in two months’ time is certainly motivating, it’s a less than optimal way to get started.  Better to have a steady income while you slowly and gradually work on your freedom plan.

The downside? It’s a hell of a lot of work. You will need to sacrifice your evenings and your weekends on a regular basis. The end game and the payoff is freedom. Freedom from being at the mercy of your bosses and co-workers, to answer only to yourself.

Only you can answer the question how bad do you want that freedom.

Start Confidently

As much as we rely on our friends to give us valuable feedback, be careful about asking your friends for advice about quitting your job.  Especially if your friends are salaried employees. By all means tell them about your endeavour and listen to their feedback. But don’t take their advice.

Employees will always offer the same perspectives about non-employees – ‘sounds risky’, ‘what if it doesn’t work’, ‘what’s your fallback plan’, ‘how do you absolutely know it will work’, ‘what if you can’t pay the bills’. You likely already have these doubts inside of you. Good. You should. It will motivate you to work harder to avoid those pitfalls. But don’t let your friends comments reinforce your doubts to the point that you fail to move forward because you’re paralyzed by fear.

Friends mean well, but if they’re working a 9-5 job, especially if it’s a job they hate, they’re likely not going to encourage you to break free of those same chains. Misery loves company.

Make sure you leave misery by itself as you walk on by.

Start, and Don’t Stop

This is the hardest step. Once you’ve started, you’ll be faced with challenges and obstacles, and even some failures. Don’t give up. If becoming sustainably self-employed was fast and easy, then everybody would do it. The secret, the secret that everyone really knows if they stop and think about it, is persistence. Do you really think that all of those people who are making a living as contractors, as consultants, as life coaches, as online business gurus, as retail flower shop owners, as caterers, as landscapers, as designers, as app builders, and on and on are really so incredibly special that they can succeed where you can’t?

Of course not. The distinction,the ONLY distinction, is that they don’t give up.  They persevere.  They believe.

Final Reminder If You Want To Be Self-Employed

When you think you can’t, when you have your doubts, when everyone tells you not to, remember this: Start now, start small, and start with something you know.  Don’t let the pessimistics and naysayers and cowards drag you down.  And after you’ve started, do not stop.


3 Key Reasons Not to Fear Failure

I was trying to think of how many times I’ve failed in my life, but who can count that high?

The interesting thing about fearing failure is that most of us do, and most of us pretend we don’t. I have absolutely no data to back up that statement, but I’d still be willing to bet on it.

Do you get up in the morning and think, “I would do X today, if I did not have a fear of failure”? Of course not. Fear of failure insidiously hides in the shadows, and disguises itself in many other costumes.

“I’d like to do X, but I just don’t have the time”.

“I’m going to do X, as soon as A, B, and C are ready and perfect”.

“I might try and do X, but I’m not going to tell anyone in case it doesn’t work out”.

The problem with all of those is that they lead to same result – inaction. X never happens. And you never know what potential wonderful results could transpire if you had just gone ahead with it.

Fear is an obstacle to everything. So here are my top three reasons not to fear failure:


Everybody Does It

Sometimes extraordinary people do extraordinary things, and you can’t help but think “I could never do that”. But failure? Everybody fails at something, as some point. From minuscule disappointments to catastrophic life altering events, failure surrounds us. So what is there to fear? Take comfort in numbers. Try something and risk failure. If the worst happens, so what? You’ll only have done what everybody else has.

Look beyond the surface of some famously successful people and you’ll see a path littered with failure and rejection. Michael Jordan was didn’t make the cut for his high school basketball team. Steven Spielberg was rejected from film school. Walt Disney was fired by an early newspaper editor for “lacking imagination”, and his early businesses went bankrupt. How different their journeys would have been had they let it stop them in their tracks.


It’s Unavoidable Anyway

I was trying to come up with an example of how you could live a life without risking failure. And I just couldn’t get there. Maybe someone smarter than me knows the answer to this. Relationships and careers require leaps of faith and have their own inherent risk of failure. But even the smaller day-to-day details of living involve some risk.

Do you ever cross the street? Even if you limit yourself to well-lit, marked crosswalks, you’re still taking a risk. Is it risking failure? Maybe a careening car comes around the corner, and runs you over. Not your failure. But maybe just after you step off the sidewalk, you glance down at your phone, ever so briefly, just to see who sent that text, and then the careening car comes around the corner, and hits you during a moment of distraction that took away your opportunity to avoid becoming roadkill. Well, then that’s on you.


No Lessons, No Learning

Ever hear the expression, “It builds character”. I used to hate that expression. During certain periods of my life, I recall thinking, “Ok, I have enough damn character now, thankyouverymuch”. But I’ve learned to appreciate the truth of it.

Failing, falling, stumbling and tumbling are how we learn. You see this repeatedly, whether it’s among kids on the playground or executives in the boardroom. Those that took their knocks and got back up again have a resilience and sharpness that is completely lacking in those that led a protected, sheltered, everything-must-go-my-way existence.

Acceptance is Progress

And since everybody fails, and since it’s unavoidable anyway, maybe it’s better to get comfortable with failure. If you never suffer the consequences, how can you ever improve?

 “Accept failure, understand it, learn from it, and ultimately, move on from it.”


How To Start a Business Without Money

Start a Business With No MoneyWhen I talk about how to start a business or the benefits of owning your business rather than working for someone else’s, people often leap to the conclusion that I’m talking about building the next Facebook.

I am not talking about building the next Facebook.

On the other hand, if you think you have what it takes to build the next Facebook, or Uber, or Google, then good for you. Make it happen. And then let me know how you did it.

But for the average 9-to-5’er who dreams of breaking free from the daily grind, there are very tangible and very attainable ways to make this happen. And no, you don’t need $1,000,000 in funding first. Or $100,000. You don’t even need $1000.

How to Start a Business With No Money

Create Value

Earning money is simple. If you can create value, you can earn money. We learn this as children, when completing chores or mowing a lawn or selling lemonade brought in that much sought after cold hard cash. The principle doesn’t change that much when you’re a grown-up. Do you have skills that other people lack? Are you willing to do work that other people shy away from? Do you have knowledge that other people seek?

When you have something that someone else needs, you’ve created value. When you’ve created value, you can earn money. Or exchange it for something you equally value, but that’s drifting too far off topic for today. Figuring out how you can provide value to earn money requires your brain, a pen and a notebook. Cost? $2.50 (plus your superior brainpower).

Tell People You Can Create Value

Tell people about your valuable thing, and how it’s for sale. People can’t buy it if they don’t know it exists. Starting a grocery delivery business? Let the people know. Tell them what you have to offer, and tell them how to get in touch with you. Keep it simple initially by creating or updating your LinkinedIn page, or Facebook page, or About.me page. Cost? $0. Pure sweat equity. And at some point you’ll need to evaluate this as well, but not just yet. Not when you’ve just started the journey.

Understand What Has Value For You

Everyone has a set of misconceptions about what they “need” to start a business. Why we have this clutter in our brains is debatable. Too many Hollywood tropes perhaps, that stick in our heads and prevent us from distiguishing between reality and fantasy. You don’t need a glass corner office in a high-rent district to start a business. You don’t need employees, at least not right away. You don’t even need business cards. You likely need a computer, or access to one. But it doesn’t need to be the best computer money can buy.

Make a list of what you absolutely need to create the value that you’re going to get paid for; not what you think you should have, or what would be cool to have, but what you need to get from point A (value realized) to point B (money received). If you’re starting a grocery delivery service, then you likely need a car. But you don’t need a Land Rover.

Understand what has real value in helping you meet your goals, and let go of optical value which exists only to impress people that you shouldn’t care about impressing. This is probably the most critical lesson for starting and running a business.

A continual process of separating substance from flash, and truth from bullshit.

Cost? Priceless.

Learn How Fear Can Motivate You

I recently took my car to a body shop, after losing the car versus snowbank battle that tends to play out in the streets of my city this time of year.  While anxiously waiting to find out the fate of my vehicle, and bank account, I spent some time chatting with the people there.

During the course of conversation, it came up that a new tenant had leased some space in the building next to theirs.  They were in the process of installing 550 cubicles.

550 neat and tidy boxes where 550 people would sit for 1800 hours a year.

Every year.

Until they retire.

Or leave for another cubicle farm.

Or die from lack of individuality.

When I first started working for myself, I was always afraid.  Afraid that I’d run out of money, afraid that the clients who were paying me would suddenly stop paying me, afraid that I’d never get another client.  Afraid that my dream could turn into a nightmare at any moment.

Those same insecurities waft across my brain every now and then, but after these many years of thriving on my own, I’ve learned to acknowledge them for what they are – motivational reminders!  So stop dwelling on the fear itself, and instead consider, really consider, how fear can motivate you.

Know Your Numbers

Instead of staying awake at night trying to mentally calculate how much money is left to pay the bills next month and the month after that, turn this fear into positive action.  Schedule time once a month to review your budget (not just professionally, but personally!).  Make sure you really need all of those things that are costing you money.  Don’t just think about your expenses, actually sit down and make a list of them in Excel, or Google Sheets, or Numbers, or another number crunching tool of choice.  List everything you can think of, and then take a hard look at whether you’re spending your money wisely.  One of the side effects of not having an employer is that you quickly become acquainted with the real value of money. There’s a passive reliance that comes into play when you’re receiving a paycheck every two weeks. It gives a false impression of security.  That’s why it’s such a jolt to suddenly lose it, whether by choice or not.

When you’re working for yourself, and your actions are so tangibly linked to earning every dollar, you take a good hard look at how each of those dollars is spent. Not only that, knowing and managing exactly how much your household and business spend every month is one of the best inputs you’ll have toward peace of mind.

Make More Money

Aside from taking stock of how you spend your money, the absolute best way to guard against running out of money is to make MORE money!   No, I’m not suggesting you start an exciting new counterfeiting business.  I’m also not suggesting that making money is as easy as wishing to do so.  But if you work on it, continually and consistently, you begin to realize that generating revenue is always achievable.  It’s demanding, and a lot of work, and requires a lot of attention; but once you have a solid understanding of what you have to offer, what value you can provide, you’ll find that you can truly discover and connect with people willing to buy what you’re selling.  Connecting with your clients and customers is the first step to making sure you always have an active revenue stream.

People get too hung up on immediacy.  Success doesn’t happen overnight.  As long as you focus on the long-term, and deliver in the short-term, you can gradually climb the path you need to realize your goals.  Give it time, keep at it, don’t give up.  These are all well-worn tropes.  But maybe there’s a reason for that; maybe they’re so well-known and so often repeated because they represent truths that we’ve gained from experience.

Biggest Fear of All

Lastly, when things get challenging, it’s good to have a conversation like the one I had recently. Because at the end of the day, my biggest fear is that I’ll someday give up and go back to being a cubicle zombie. Who needs more motivation than that?!