Should I go freelance?

If you’re considering going freelance but scared to take the plunge, this course is for you.

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Easy business development for freelancers.

If you hate sales but want to build your client list and get the right kind of work, look no further.

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Optimal client management for freelancers.

Do you feel like freelancing would be great if it weren’t for the endless demands of your clients? I wrote this course for you.

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What I learned from a month of remote working

I spent January 2018 remote working in Montevideo, Uruguay. I’ve been excited about this experience for months, and for good reason – it’s been incredible spending a month I normally have to trudge through (I’m not a Winter person) enjoying summer sunshine, palm trees and ocean breezes, as well as light-filled skies until 9:00pm.

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How I chose my remote work location

Last March, I decided that I would spend January 2018 remote working. Anyone currently living through Toronto’s winter doesn’t need me to explain what prompted the decision. For the next four weeks, I will be living and working in Montevideo, the capital of Uruguay.

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Three unexpected traits that help me thrive as a freelancer (part three)

The final part of my three-part series on unexpected traits that help me thrive as a freelancer  (find parts one and two here) may be the most unexpected. It is the ability to let go. You may wonder what this ability has to do with a healthy freelance practice, but it’s surprisingly important. Not to mention, the list of things you need to release is unexpectedly long. The first item on the chopping block is the perks of full-time employment. That may sound strange, since many people compare quitting their 9-to-5 to winning the lottery. But it’s not that simple. In my experience, the inability to let go of the benefits of being an employee is one of the most common reasons people quit freelancing. These benefits include: Financial security – this is the most obvious and for many the biggest loss of giving up full-time employment. For the first year or so of self-employment, I regularly woke up in the middle of the night in a panic, wondering where my next paying job would come from. The camaraderie of co-workers – I’ve always really enjoyed the social aspect of work and working from home was initially very tough. Some days, it still is. While co-working spaces and working in clients’ offices can help, nothing replaces the close-knit friendships you make with co-workers. The feeling of belonging – love or hate your job, feeling like you have a place in the world is important. When I first quit my job I felt unaffiliated and bereft. How was I supposed to fill my days now that I wasn’t accountable to anybody for what I accomplished during work hours? How do you go from being invested in the well-being of an organization to creating your own thing? These things become less critical as you get invested in your own practice. But here too, you have to let go of things to progress. In fact, there’s a whole new list of items to release: Your insecurity about never working again – it’s fear that the phone will never ring again that makes consultants take on projects that aren’t right for them or undercharge for their services. You’ve got to know that the practice that you built is standing on a solid foundation and make the choices that support it. Your self-limiting beliefs – every time you stretch yourself beyond your current experience level or skill sets, the inner alarm bells ring. You’ve got to learn to keep going anyway, and prove yourself wrong. Nothing alleviates imposter syndrome short of actually doing the thing that initially makes you feel like an imposter. The outcome of your efforts – The harder I hold on to my hopes of winning a certain project, the more stressed I get. This stress impacts my other work, which then makes me feel worse. Similarly, worrying about whether or not the effort to speak or teach will be worth it just makes the process taxing instead of enjoyable. Challenging as it is, you have to learn to put forth the effort for the experience as opposed to strictly for the results. Your mistakes – It can be harder to make mistakes as a freelancer than as an employee, since it directly affects your bottom line and you’ve got no one to blame but yourself. But mental flogging only brings bad energy to your other projects. You’ve got to learn to let go of the mistake while keeping the lesson. The fear and grief associated with letting go is natural, but as you slowly untether from society’s security blankets, you’ll also start to appreciate how much easier it is to act with integrity and in a manner that is true to yourself. For me, learning to let go began with my personal effects – after following The Minimalists, I began a year-long de-clutter of my home. The repeated act of assessing which things to keep and which to release eventually prompted me to re-assess everything in my life, from my relationships to my habits to my beliefs. Start small, and question everything. If it’s not absolutely essential, it’s expendable. This post was originally published on November 14, 2017

Three unexpected traits that help me thrive as a freelancer (part two)

Last week I started my three-part series on (unexpected) traits that help me thrive as a freelancer (find parts one and three here). Part one covered the importance of the ability to play the long game. Part two is in line with this in that it also requires patience – an iterative mindset. When you think about the risks that you haven’t taken in life, what is the barrier that typically holds you back? For most of us, it is fear – the fear of failure. Many of us struggle with the idea of having to potentially face the fact that if we actually try, we won’t live up to what we think is our potential. We believe that if things don’t work out, we’ll feel shame, along with the sting of other people’s judgment. Our cherished notion that if we tried [NAME THAT VENTURE], we’d be a superstar can only be killed by one thing – actually stepping up to the plate. The truth is, I’ve “failed” at a number of things since going freelance. But in reality, I haven’t failed at anything. I’ve simply made a first attempt that underperformed. You may chuckle thinking that I’m up-phrasing, but I honestly don’t see it that way. If you think about any professional skill you’ve mastered, from doing a great interview to giving a memorable presentation, the odds are that the first time you tried it was not your best. The same is true of consulting. As with anything challenging, you’ll make a number of gaffes in the beginning. The first time I arranged a networking lunch, I felt so awkward paying for the meal that I just didn’t offer. We split the cheque. It’s still embarrassing to remember that incident, but over the years I have gotten much more comfortable having these lunches, to the point where I actually enjoy (and pay!) for them. As a newbie blogger, I’m hardly setting any records for readership, but each post I write, I gain a little more understanding of what topics really resonate and how to write a solid headline to support it. These things are a little tough to admit, but they would only be failures in my eyes if I stopped after the first attempt. I have always been someone who sees things iteratively, from mastering my chili recipe to managing my consulting practice. The key to this mindset is to consider your latest effort not as a failure, but as the new benchmark on the ultimate journey to mastering the skill. One thing that will help you master this mindset is to regularly consider how much you’ve progressed from when you first started, or even from your last attempt. If this sounds like motherhood, or the message in a “very special” sitcom episode, consider how many things you’re holding yourself back from doing because you’re worried you won’t do well, that you’re not as good as you want to think you are. Seth Godin, seemingly the only person who can talk about failure without sounding like a cat poster (“Hang in there!”), said: “If you don’t start, you will fail. Not starting and failing lead to the same outcome, with different names”. Now, if you’ll excuse me, I’m off to try writing another blog post. This post was originally published on November 7, 2017

Three unexpected traits that help me thrive as a freelancer (part one)

Last week I read an article called Unexpected Signs that You Might Be an Entrepreneur. That got me thinking, what are the unexpected attributes that differentiate someone with a thriving freelance practice from someone who struggles? There may be many, but for me personally, it has come down to three. In the interests of keeping these posts short, I’m going to write a separate blog post on each one (find parts two and three here), citing how it helped me get my practice to where it is today. If you agree that this trait is an integral part of freelancing/entrepreneurship, feel free to share how you’ve used it to grow your own practice in the comments area below. Trait Number One – The Ability to Play the Long Game For the first few years of my practice, almost all of my work was for the same company. The advantage of that was the predictable income, but it’s easy to see why it’s not a good long-term strategy. Any business that is overly reliant (or, in my case, entirely reliant) on a few key clients is vulnerable. If anything happens to your client or to the relationship, the gravy train makes an unexpectedly abrupt stop. Even though I knew it would mean hard times in the short-term, I decided a few years ago to cut back my work with this client in order to invest more time into prospecting, networking and creating a more solid foundation for myself in my industry. Many long, hard days and months of (metaphorical) unanswered door knocking followed. During that time, I frequently questioned my strategy and even thought longingly about returning to life as a full-time employee. Finally, my first new client came on-board. A short time after that, the next client followed, and things have snowballed from there. After I had amped up my client list, I decided it would be a good idea to increase my profile within my industry. I didn’t know much about how to do that, but decided to focus on storytelling since that’s what I’m passionate about. I spoke at a conference and at a lunch and learn, and eventually developed a course on the topic. It takes a lot of time to develop original content and learn how to deliver it smoothly, and I had no idea whether or not the effort would pay off in terms of increased profile or new clients. But if you take a moment to think about your own industry, who are the thought leaders, the people whose names you know even if you’ve never met them? You can bet those people have taken the time to develop their own content, whether it be presentations, courses, videos or blog posts. The Long Game is a psychological endurance test because you don’t know whether or not your hard work will pay off. You need to get up each morning and put forth the effort, never sure if it will pay dividends. In the beginning, there are days when it is truly a slog. Those are the days when mental fortitude (and a solid source of emotional support) are required. You can expect to have a few emotional breakdowns. But as the first dividends start to trickle in, it will breed the kind of satisfaction that only sweat equity can offer. You can’t beat the pride of creating something from scratch. Martin Luther King Jr. said ‘Faith is taking the first step even when you don’t see the whole staircase’. That’s pretty much the definition of playing the long game. You keep taking step after step, hoping it’s going to work out, placing that bet on yourself. It’s tough, that’s for sure, but up to this point, I’ve never invested my time and thought ‘wow, I regret that, what a waste’. I’m betting you won’t, either. This post was originally published on October 29, 2017

Why consultants need to learn to say “No”.

When we first try something new, most of us are in “play it safe” mode. If you’ve ever bought a house, chances are you chose a fixed interest rate for your first mortgage, despite the fact that a variable rate is often the wiser choice. Similarly, when starting a consulting practice, most of us will take every job that comes our way whether or not we find it interesting or it’s in our area of expertise. It’s better to have a gig, we think, than not to. For a long time, I knew that I wanted to focus on work that was more strategic rather than strictly executional, but I took on many projects that didn’t reflect that. I had a “survival” mindset that led me to work on certain projects that didn’t stretch or engage me. I was proud of the fact that I was paying the bills, but I also wondered why I didn’t feel very fulfilled. Then last year I experienced a gutting moment – I was offered a great project, one that I could really sink my teeth into. But I couldn’t take it, because at that time I simply didn’t have the capacity. I thought about what I was giving up that dream job for. Don’t get me wrong – many of the projects I work on are interesting, thought-provoking and thoroughly enjoyable. But at that particular moment, this was not the case. I gave up a great project for what amounted to analyst work. Gratitude is an important component of a successful consulting practice. However, in the long-term, taking on every job you’re offered will feel like a grind. At a certain point, you’ll have to decide what you want your practice, and your life, to look like, and start choosing accordingly. Knowing how I want to invest my time, I have started to run potential projects through the filter questions below. This more strategic approach has had a notable impact on my career fulfillment. ·       Does this project reflect the kind of work that really engages me? ·       Will it be enriching? Will I stretch myself as a consultant? ·       Will this project give me the flexibility that I want? ·       Will this project lead to other interesting opportunities? ·       If I had to give up a great project for this one, would I be okay with that? Being thoughtful with your practice is an important step to creating a rewarding long-term career. While we all need to work a certain amount to survive, consultants, unlike most employees, have the opportunity to make choices based on whether or not they are aligned with their values and their vision. It’s worth thinking through what you really want for yourself, and whether or not your choices reflect that. This post was originally published on September 26, 2017

How to conquer your fear of going freelance

Many skilled professionals confess to me that they’ve been thinking about becoming an independent consultant for a long time, but something is holding them back. Of course, that something is Fear. I can certainly understand that Fear – the potential rewards of consulting are substantial, but the stakes are also very high. Most of us require a certain income level to sustain ourselves, and the pressure is even higher for those with a family to support. Finally cutting the cord and setting up a freelance practice is just the start of the anxiety that new consultants will face. First, there is the sweaty-palms discomfort of learning how to speak confidently about your professional rate. Then, there is the gnawing anxiety when the phone doesn’t ring for a while. This is followed by the pulse-racing stress of having to manage a deadline during a technology crash. Then it’s the pressure of landing the first assignment that really takes you out of your professional comfort zone. Finally, if your practice has survived this long, you get to move on to the Mac Daddy of all fears – the abject terror of public speaking to increase your exposure. But in facing and managing all of those fears, I’ve learned something empowering and important: the more fear you take on, the less control fear has over you. In his book The Seven Habits of Highly Effective People, Stephen Covey talks about the Circle of Influence – these are the areas in which we have some control over our life concerns. His advice is to focus your problem-solving activities in your Circle of Influence – and you will see that circle grow. Lately I’ve been thinking of Fear as having a Circle of Influence too. Depending on the individual, Fear’s Circle of Influence over them can be huge, or quite small. If your Fear has a large Circle of Influence over you, you have a limited comfort zone and appetite for risk and therefore limit your experiences, both personal and professional. We hear this a lot when people say: “I’d love to [fill in the blank]”, and then state some flimsy excuse why they “can’t” do that thing that essentially means “I’d love to [fill in the blank], but I’m scared”. Happily, I’ve learned that as you begin to face your Fear, its Circle of Influence slowly diminishes. So, the things that seemed like a huge deal to me four years ago are pretty much par for the course now. Not that long ago I couldn’t turn down work (even if I knew it wasn’t the right work for me) because I was scared that nothing else would come along. Now I know I don’t do myself or my clients any favours taking on projects that are wrong for me. The first time I taught my course The Essentials of Research Storytelling, I was terrified. Now I get excited to teach it because it’s a subject I’m passionate about. Thinking of fear as having a movable Circle of Influence is empowering because it means that that circle will get smaller with each step that you take. If going from full-time employee to full-time freelance consultant is too big a leap, then the key is to just keep taking steps towards your goal. Start small and get bolder and bolder. First, learn to not just survive, but thrive, in a networking situation. Then, start posting regular blog posts on your area of expertise to get comfortable in a thought-leadership role. After that, maybe it will be time to take on some part-time consulting work on the side. Each step along the way is going to be daunting and uncomfortable, but as Fear’s Circle of Influence slowly diminishes, your power, and your professional options, will grow. This post was originally published on September 18, 2017

Downtime: turning my greatest fear into an asset

This post was originally published on December 3, 2015

When people ask me how I like having an independent practice, I tell them that I enjoy it, that it’s stretching me beyond where I was before, both as a consultant and as a person. But I also tell them that, like anything, making this choice has involved trade-offs. One of the biggest trade-offs for me is living through the down periods, those times when the emails don’t come and the phone doesn’t ring.

Making the choice to go solo was exhilarating, but also terrifying. All my life, I (like most people) have been affiliated with organizations of some sort – first school, then work – which shaped much of how I spent my time and the things that I accomplished. There is a particular kind of terror that comes with letting go of those affiliations, much like diving off a cliff into the surf below, hoping that you are going to emerge from the turquoise waters unscathed and not jump head-first into a pile of craggy rocks.

Lately I’ve noticed that I am getting better at managing the down times. Having been through it before, I’m starting to understand that not only is this part of the drill, but that these periods have also taught me some valuable lessons. I thought I’d share some of them here, since I’m guessing many of you will relate to this situation in one way or another.

Things don’t always come at the time that you want them to, and that’s okay

When your work involves providing a service to others, you must learn to accept that you are not necessarily in control of how much work you have when. When this gets frustrating, I remember a quote from author David G. Allen: “Patience is the calm acceptance that things can happen in a different order than the one you have in mind.” And then, in addition to pursuing professional opportunities, I look for life opportunities to fulfill that I might not have had the time to address if I had a standard full-time job.

Celebrate the small wins, because they’re the precursor to the bigger ones

It can be easy to dismiss the significance of a conversation or an email, but I have learned from experience that a series of little wins can ultimately add up to interesting work and a thriving practice. The easiest way for me to move myself from fear mode back to peace and productivity is to consider how much I have going on compared to the previous year. While I still have a way to go, there is room to celebrate at every stop along the way.

Reward yourself for the effort, not necessarily the results

There’s always more to strive for and I’ve found that if I only reward myself for major wins, I get a warped view of what I’ve accomplished. It’s worth feeling good about every new conversation you have and every new contact you make. After all, if my practice is just a never-ending slog to a new finish line, why do it?

Playing the long game DOES ultimately get results

It’s a well-known adage of sales that most people give up after contacting a prospect a few times, but successful sales can take 10+ contacts. Each time I reach out to my contacts, I’m pleasantly surprised to see a few new individuals responding in a way that forwards our relationship a little bit. I try to provide content with some insight and value, and it’s always interesting to see who responds to what.

When the things you want aren’t happening, make other things happen

After a rough start to 2015, I decided to reach out and look for speaking engagements. After all, putting together a talk was something I could control and accomplish without relying on others. I have found speaking publicly to be tremendously helpful in establishing new contacts as well as professional credibility. And from these engagements other things have started to happen, which further legitimates the effort.

In addition to helping me thrive during leaner periods, the beauty of a lot of these learnings is how they apply to so many other things in my life. Part of the reason that I began an independent practice was that I felt a need to branch out and stretch myself. You never know what you’re going to get when you take these metaphorical leaps, but experience has taught me that the end result, while typically looking different than I imagined, will be worthwhile.

Here’s to a happy and productive 2016 for all of us.