I’d been setting aside part of my budget for an “opportunity fund” ever since I graduated with a master’s degree and started working at IBM. On February 17, 2012, after four wonderful years of web development and consulting, I turned over all of my projects and started on my own adventure. Two days later, I had a federal corporation that could be the umbrella for various experiments. By March, I had my first paying clients for consulting, and I was off and running.

2012-12-15 5-year experiment

Why this experiment?

Not many people have the time or space to find out what can happen if you don’t have to worry so much about making money. I wanted to see what could happen if you explored that.

Why five years?

Statistically speaking, most businesses struggle within the first five years. People have to learn how to run businesses. People have to find product-market fit. People have to figure things out. If I prepare for those challenges by remembering that it’s normal to struggle and telling myself that I won’t consider going back to employment until at least five years have passed, then I can hang in there even when times are tough. And if times are really tough, knowing that the experiment is time-bound will also help me stay sane.

I’m open to considering employment if our circumstances change drastically, but so far, I’m still on track.

What have you learned so far?

While it can be stressful learning about things like sales, marketing, and accounting — all the things you’re insulated from in a corporate environment — I also really like learning how to build a business. Lots of people are happy to help you out along the way, too. In addition to learning more about business, I also want to use this time to learn more about life.

How can you afford not having a regular paycheque?

I saved up a lot when I was working at IBM. Initially, I carved out enough from my savings to plan for five years of expenses, and that allowed me to give myself permission to start with this experiment. I had other savings beyond that, too. Since I’ve been adding to it with consulting and other things (and the stock market has been doing really well), it looks like my experiment can continue for quite a while yet.

How is the money working out?

W- and I are frugal, and that’s been a key factor in making this experiment possible. We keep our expenses low through cooking, simple leisure activities, and self-discipline. My personal finances are approximately where I projected they would be. In terms of business income, I’m ahead of where I expected to be (thanks to people taking a chance on a business that’s starting up, hooray!), but I’ve left most of the money in the business so that it can build its own emergency fund. (And to simplify paperwork…)

2014-02-24 Yes, but how do you make money #experiment #business

How’s W- dealing with it?

Wonderfully. We think it’s a great idea for me to be learning entrepreneurial skills. It’s the new job security, after all. This would be much more difficult without his support.

What are you up to now?

I share what I learn on my personal blog. One of my experiments has graduated into a business that I’m learning how to sell and market. Looking forward to learning even more!

What do you want to get out of this experiment?

2014-02-19 Imagining wild success for this experiment #experiment.png

2014-02-28 What outcomes do I care about #experiment

You’re just lucky.

Yes, I’m incredibly lucky. I grew up reading personal finance books, and I started saving and investing early. I graduated with a bachelor’s and a master’s degree without student debt, thanks to support from my parents and various scholarships. W- is frugal, supportive, geeky, and totally awesome. I live in Canada and W- has a great health plan, so many of my health expenses are covered. I’m not completely worried about a gap in my resume because I’ve seen many women start second or third careers after taking time off. (It might be tough, but it’s not impossible.) I can communicate well, and my blog has helped me connect with people even though I’d be too introverted to reach out in real life. I’m not greedy – I don’t need to beat the market, so I don’t take crazy risks. So yeah, I’m really lucky.

You might be lucky too, in different ways. I’m not saying this path is for everyone, but hey, if you think it’s interesting, you might give it (or something like it) a try. =)

Can I hire you for stuff?

See Reflecting on what I want to contribute to and how interested people might (semi-)work with me.

Read other experiment-related posts by clicking on individual posts below or reading the category of posts:

• What did I learn from this experiment with semi-retirement? - I’m so glad I started this experiment! The timing worked out perfectly. I was pretty happy with the corporate world, but I also wanted to learn about all sorts of things that don’t fit into the usual 9 to 5. I learned that I can have fun building very different kinds of businesses, and that […]
• How do I want consulting to fit into my life? - I do a tiny bit of consulting to help a long-standing client with prototyping and data analysis. It lets them take advantage of the experience I’d built up with their tools and platform, and I get to keep my technical skills and professional network going. Before we went on our trip, I was averaging about […]
• A reflection on leisure and discretionary time - I’m coming up to the 4-year mark of this 5-year experiment with semi-retirement. The start of the final year might even neatly coincide with the next substantial change I’ve been planning. I’ve been very lucky to have had this opportunity to explore, and it’s a good opportunity to reflect on self-direction and leisure. This past […]
• Moving past getting things done - 2015-06-19a Moving past getting things done – index card #present #mindset #being When I have a lot of energy, it's easy to do good things for my consulting clients or on my personal projects. This energizes me further, and so on. This is a good cycle. When I'm feeling blah, or when I don't feel […]
• Tweaking my daily routines for that feeling of progress - I found myself feeling like I hadn't gotten a lot of things done. My weekly reviews showed me I made progress, but it didn't feel like it day to day. I thought about what I'd like to feel instead. 2015-05-04c Keeping the end of the day in mind – index card #life #quality-of-life A little structure […]
• From dreams to experiments - Since my childhood, my parents have always told me to follow my dreams. It wasn't just the usual maxim passed on from books and the child-raising culture of the time. I had proof of the power of dreams in the adventures of my father. I talked to my parents last weekend. They're a little worried […]
• Quiet afternoons and weeks - I work about one day a week, sometimes less: enough to keep interesting things on the go at my consulting client, and with plenty of space for other things in my life. 2015-04-23e Working once a week – index card #consulting #pace #experiment It's been a little tricky working once a week, since the communication […]
• Learning from a diversity of ways to live a significant life - I have plenty of role models in terms of people who've done wonderful things as part of regular careers and entrepreneurs who've created products or services. I even have a few role models who've explored alternative paths: simple living, writing, arts, crafts, trades… I love having such a diversity of life paths illuminated for me, […]
• Being extra-kind to myself - I enjoy an awesome life in general, so it feels a little indulgent to focus on making it better. But for the next few weeks, I think I'll experiment by being even kinder to myself. It's not just a matter of spending the entire day reading or playing video games… (On the plus side, W- […]
• Considering tech and the home - I came across an interesting exercise in Barbara Sher's I Could Do Anythng If I Only Knew What It Was: to pick a scenario and try fully committing to it, even just for a little while. Let's say that this current lifestyle is the thing that I'm going to fully explore. I've started thinking of […]
• Starting from a small life - The impression I get from people's descriptions of their lives or careers is that many people (or at least the ones who talk about stuff like this) go for a big goal. They want to influence lots of people. They want to make a big difference. Sometimes it works out really well, but there are […]
• What do I want to get ready for next? - I've been thinking about what I should prepare for during the fourth year of my experiment. The first year was about exploring business. The second year was about digging deeper. The third year focused on self-care. I still don't know what shape my life will take in my fifth year and beyond, but I can […]
• Learning to live slowly - Sometimes I feel a little duller around the edges, not quite as alert. It’s a little harder to think, to reason. I feel slightly out of focus. I talk more slowly, move more slowly. And yet, living more slowly, I feel like I live more gracefully as well. None of the sharp jitters when my […]
• Different dimensions of scaling up - When I was coming up with a three-word life philosophy, learn – share – scale felt like a natural fit for me (Nov 2012). Learning and sharing were pretty straightforward. I thought of scaling in terms of sharing with more people, sharing more effectively, building tools to help people save time, connecting the dots among […]
• The 5-year experiment: A conversation with my anxious side, and how sharing time might be better than giving money - (If you want, you can skip past the reflection on anxiety and safety and jump straight to the part on how you can help. =) ) Having resolved to learn how to work on my own things, I'm experimenting with reducing my consulting to one day a week (from last year's routine of two days […]
• Finding a model for my sharing - Can a sharing model based on free/pay-what-you-want resources be sustainable over a long period of time? I've been thinking about this for a number of reasons: One of my assistants e-mailed me about my difficulties with delegation. He suggested thinking of my life as a business: What would my objectives be? When I reflected on […]
• Learning to work on my own things - It’s easy to say yes to other people’s requests, but it might be worthwhile to learn how to come up with your own.
• Filling in the occupational blanks - Following up on an interview, a journalist asked: If I were to say that you freelance as [blank] consultant, what would be the word that fills that blank? 2015-01-14 Filling in the occupational blanks – index card #experiment #occupation Tricky question. "Freelance" is definitely the wrong word for it, since I doubt I'll be taking […]
• When you feel like you’re spending a lot of time on low-impact activities - Embracing your constraints, laying the groundwork for action, acting in tune with yourself, and accumulating gradual progress can help you keep moving forward even if it feels like you're taking such tiny steps.
• Relaxed routines - Where I tell people it's okay to have a relaxed, not-crammed-to-the-gills schedule, and I extol the benefits of slowing down and taking notes
• Learning slack - Amy Hoy’s post “Don’t write 1000 words a day” goes: What would bring a person to ask, “How do you motivate yourself?” … This question presumes that You are not a single entity, but a split one: a cart driver, and a donkey. The cart driver is trying to flog the donkey and the donkey […]
• What could I do if I showed up in a bigger way? - Among the different communities I care about, Emacs still tickles my brain the most.
• Reducing my consulting - I’ve been gradually scaling down my consulting. I started with a plan for consulting 3-4 days a week. Then I shifted to 2-3 days. Now I’m planning to target a regular schedule of one day per week, with extra for when there are important projects. I’ve been helping other team members pick up my skills, […]
• Thinking about rewards and recognition since I’m on my own - One of the things a good manager does is to recognize and reward people’s achievements, especially if people exceeded expectations. A large corporation might have some standard ways to reward good work: a team lunch, movie tickets, gift certificates, days off, reward points, events, and so on. Startups and small businesses might be able to […]
• Recovering from a sprint - Still a little tired from my work sprint, but I’m starting to feel the fog receding. I spent yesterday evening helping at Hacklab, holding up cabinets and assembling Ikea shelves. It was a little bit more work when I could be relaxing or helping out at home, but it will pay off, I think. My client […]
• Crunch mode - I’m working more intensely than I expected to do at this point in time, roughly halfway through my 5-year experiment. I had planned to wind down to two days a week of consulting, or even one or zero. Instead, I’m working on a potentially high-profile project with shifting requirements and technology risk. I can definitely tell […]
• Doing more consulting - As I mentioned previously, I’ve been doing a lot more consulting than I originally planned. At this point, I had been thinking of keeping my twice-a-week schedule for a few months, and then tapering down to the equivalent of one day a week, and then eventually letting go of it entirely. That might still happen. […]
• Planning ahead for experiments - Experimenting doesn’t have to be about coming up with conclusive answers. It can be about reducing uncertainty and increasing understanding. For example, compared to where I was at the beginning of this 5-year experiment with semi-retirement, I’m more comfortable with business. There are fewer unknowns in my life. No, actually–there are just as many unknowns, I […]
• Anticipating experiment outcomes - I’m almost half-way through this 5-year experiment with semi-retirement. Every so often, I like reflecting on the possible outcomes and whether I want to influence things one way or another. (Totally unscientific here!) Thinking about this will also help me figure out what I need to try so that I can properly discriminate among the […]
• Nudging the balance toward work - As an experiment, I decided to work a lot more last week than I normally do. I made work my default activity. If I didn’t have something particularly interesting in mind to write or draw or read, I’d log on to the network and check for requests, work on prototypes, and follow up on things I needed to do. […]
• Thinking about leisure activities: noble, advantageous, pleasant - As an experiment (and because the timing works), I have a three-month break coming up. It’ll be quite a different experience from the 1-month breaks I’ve been taking so far, probably as different as the way that having an entire weekday to yourself is different from squeezing your activities into an evening. So I have […]
• Learning from frugal lives of years past - I’ve been reading a lot about early frugal living. I read Henry David Thoreau’s Walden (1854), and I followed a link in a blog post to Ralph Borsodi’s This Ugly Civilization (1929) and thence to his Flight from the City (1933, during the Great Depression – particularly poignant bits in the chapter on security versus […]
• Planning my next little business - I’ve been holding back from experimenting with new businesses. I’m not sure how the next few months are going to be like, and I don’t want to make commitments like sketchnote event bookings or additional freelance contracts. Besides, focusing on my own stuff has been an interesting experiment so far, and I want to continue […]
• Quiet days - I set aside Tuesdays and Thursdays for consulting. Fridays are for meetings and getting together with people. Saturdays are for spending time with my husband or having the rare party, and Sundays are for cooking and chores. Mondays, Wednesdays, and Fridays are discretionary time. I could spend those days working. My consulting clients would love […]
• Hmm, maybe I’m not slacking off after all - Even though I’ve got the steady accumulation of DONE tasks showing my slow-but-constant progress, I still sometimes feel like I’m leaving something on the table when it comes to how I use my time. I feel like I’m living with a more relaxed pace, especially compared with the world of work around me or my fuzzed-by-time recollections of […]
• Reflecting on risk aversion - I’m more careful about risks than I was at the beginning of this experiment. I see more negative consequences when projecting the results of decisions, and I perceive more volatility. I tend to overestimate the probability and impact of negative possibilities, and I’m conservative about taking advantage of opportunities. This is interesting to me because […]
• Thinking about what I want to do with my time - Every so often, I spend time thinking about what I want to focus on. I’m interested in many things. I like following my interests. Guiding them to focus on two or three key areas helps me avoid feeling split apart or frazzled. I balance this thinking with the time I spend actually doing things. It’s […]
• Planning ahead for the stories - Sometimes, when you take risks or make decisions, it helps to think about how your choices affect your story. We all tell stories. Stories are how we make sense of things. The same set of facts can support many different kinds of stories. The story you choose to tell–the perspective you pick–affects how other people […]
• Reinvesting time and money into Emacs - I received a wonderful token of appreciation from someone who found my Emacs posts useful. It got me thinking: what would it be like if I made Emacs a large part of my life’s work, and how can I invest even more into it? Emacs is already a big part of my life. I like […]
• Rethinking my time categories: the blurring of business and discretionary activities - I track my time with medium-level categories (not detailed enough that I’m tracking individual tasks, but not so high level that it’s hard to make sense of the data). From time to time, I notice categories drift, or they stop fitting. Consulting is definitely business, but does working on Emacs really belong there? Why is coding classified […]
• Working fast and slow - When it comes to personal projects, when does it make sense to work quickly and when does it make sense to work slowly? I’ve been talking to people about how they balance client work with personal projects. It can be tempting to focus on client work because that comes with clear tasks and feedback. People’s […]
• Experiment update: Mid-term pre-mortem check - In the early days of my 5-year experiment with semi-retirement, I brainstormed ways it could fail. I worried that I might end up too distracted to make useful stuff, or that I’d end up being incapable of pursuing my ideas, or that I’d mess up somewhere–paperwork, people, products–and botch the whole thing. I worried that […]
• Going fishing for three years - People often ask me if I could draw for them, or write for them, or code for them. I refer all that business to other people. Here’s why. You see, some people want to learn how to fish. These are the people who want to learn more about sketchnoting or Emacs or other things I’m interested in. […]
• Reflecting on what I want to contribute to and how interested people might (semi-)work with me - From time to time, people ask me if I’d be interested in working with them to make something bigger happen. I’m getting better at saying no. I want to focus on learning how to direct my own life. Other-directed work is seductive. Clear tasks! Appreciation! My mind wanders back to it, thinking about whether it’s […]
• Reflections on infopreneurship - There’s a lot of information on how you can build an online business by selling what you know. Many people are looking for that dream. It feels a little weird to me, and I want to figure out why. I guess one of the things that rubs me the wrong way is that a lot […]
• Reflection: Two years into my 5-year experiment - “Monotony collapses time; novelty expands it,” writes Joshua Foer in Moonwalking with Einstein. It feels like more than two years since the start of my 5-year experiment with semi-retirement, which is what I jokingly called this adventure into a self-directed life. So far, amazing. This year, I focused less on consulting and event sketchnoting, and I […]
• Reflections on learning to be an entrepreneur - The other week, I focused on exploring ideas and becoming my own client. Last week, I focused on the systems I can set up in order to keep on sharing while I’m distracted by work or other needs. The other week felt happier and more self-directed, but on reflection, last week is great for long-term […]
• A conversation about writing, and reflections on taskmasters - I’m fascinated by the idiosyncrasies of systems that we build for ourselves over decades. I’m particularly interested in what people find weird about themselves and their systems; what they do the most differently compared to other people. When John Allemang picked my brain about a piece on the Quantified Self, I jumped at the opportunity […]
• Other-work and self-work - Since I decided to become my own client, I’ve been thinking about the things I think of as work and the things I do out of my own volition. Work is shaped by other people’s goals, priorities, and directions. When it comes to the things I do for myself, I am responsible for figuring all […]
• Becoming my own client; also, delegation - When I started this 5-year experiment with semi-retirement, I fully intended it to be a learning experience in entrepreneurship. I wanted to learn how to create value. I wanted to learn how to sell, how to build systems. Mission accomplished. I have the confidence that if I need to work, I can help people and […]
• The power of no: being completely* unhireable until 2017 (and possibly longer) - When I started this 5-year experiment, I didn’t know if I could stick with it. My track record for sticking with interests is not that good. I’m delighted to report that (semi-)retirement gets easier and easier. I am learning to say no. By coincidence, two of my mentors (who had moved on to separate companies […]
• Reflecting on a month of experimenting with Proper Retirement - When I started on my 5-year experiment, I hedged my bets by thinking of it as semi-retirement. I was open to working part-time on a flexible basis. Consulting worked out well for that. People also wanted me to work on illustrations and sketchnotes, and I figured that was a great way to spread visual thinking […]
• On making big, scary decisions, and how I left an awesome job to do my own thing; or how to be a Builder Lemming - Following up on my Accelerated Learning chat with Timothy Kenny, where someone asked how I made the decision to go on this 5-year experiment with semi-retirement: It might surprise you, but I consider myself pretty risk-averse. I don’t bungee jump. I don’t ski. I don’t even drive. I spend hours and days analyzing decisions. I […]
• Thinking about business cards - I’m nearly out of business cards, which means it’s time to evaluate my business card experiment and plan my next one. Past performance is a good indicator of future results, so let me think about how I’ve been using my business cards and how I want to use them in the future. For comparison, here’s […]
• Business experience report: Setting up payroll and benefits - Another big milestone in my business adventures: I paid myself for the first time! Not bad, considering this is my second fiscal year. I’ve been nervous about this for a while because I wanted to make sure that the business had a emergency fund of its own, especially when it comes to taxes. I also […]
• Choosing openness and scale - Summary: Until June 2014, I’m focusing on work that’s either public or that reaches an audience of 10,000+.  I’m celebrating my 30th birthday next month. To get a sense of where I’ve come from and where I want to go, I’ve been reviewing more than ten years of blog posts. If I didn’t have my […]
• How hacking my wants helped me experiment with early retirement - During his Third Tuesday Toronto talk on How to Live an Amazing Life (see notes), C.C. Chapman saw me sketchnoting near the front and called it out as an example of a creative and unusual profession. He asked (probably rhetorically) how I explain it to other people. I said that I usually told people I […]
• Things I’m learning about semi-retirement - I’m really glad I track my time, because I get to ask questions about long-term patterns. It turns out that I haven’t been as retired as I joke about. It’s been 64 weeks since the week beginning March 3, 2012, which included my first major gig as an independent person. I’ve tracked an average of […]
• Experiment notes: Accounting, sales, and marketing–all the other parts of a business - When I started my experiment last year, leaving the familiarity of web development at IBM for my own adventures, I wanted to dig into several big unknowns that I had little experience with: the paperwork and accounting required for business, and the sales and marketing that’s even more crucial to business survival. I had tracked […]
• Planning my code/development learning - One of the best things about programming is that as you learn more, the possibilities increase dramatically. Each new thing you learn can be combined with so many other things for even more awesomeness. I’m getting ready for my idea-of-the-month experiment, and I’m thinking about the kinds of building blocks I’d like to learn more […]
• Accelerating my business learning: setting a goal for a new business every month - The first year of my five-year experiment is going well. I learned how to set up the structures for five different kinds of service businesses: web development contracting social business consulting illustration conference/event sketchnoting public speaking and two kinds of product businesses: writing e-books selling used books … and I got to my first sale […]
• Experience report: Naming my company! - Ten months after incorporation, I’ve finally come up with a name for my company. I wanted to combine the different aspects that resonated with me and with other people during conversations and events. Consulting was easy to do under my own name and with a numbered company, but if I want to expand to channel […]
• Experiment pre-mortem: Imagining and dealing with causes of failure - I am, for the most part, a relentless optimist. I embrace my inner Pollyanna. I regularly explore my goals with the Imagine Wild Success technique. Most people know this part of me, because I’m often the first to find the silver lining in any cloud. Here’s something less visible but also very useful: I also […]
• Taking a month off from consulting - I’m taking all of September off from consulting so that I can present at a conference, spend time with family, and work on other skills. This five-month consulting engagement has been absolutely wonderful. It turns out that you can create tremendous value as a generalist with technical, business, and design skills, and that good engagements […]
• This is what five years looks like - I was thinking about my experiments with entrepreneurship the other day, and I realized that I have a lot of room to learn things. Books tell me it takes about five years for many businesses to shake out the bugs and settle down; even then, only about half of new ventures survive the first five […]
• Experience report: So much for having a virtual bookstore - As part of my experiments in entrepreneurship, I decided to try out selling used books online. I like books, and am happy to keep a small library of my favourite titles in order to reread, give to friends, or resell. I checked out Toronto Reference Library’s bookstore, focusing on donated hardcover business books that had […]
• Experience report: Applying for a Harmonized Sales Tax account - In Canada, corporations are required to collect and remit Harmonized Sales Tax if their revenues are over $30,000 in a year or if they meet certain other conditions. If you’re starting out, it might be a good idea to register for an account anyway. That way, you don’t have to change things when you do […]
• Experience report: Opening the RBC Small Business eAccount - Having a business bank account is good for separating business and personal expenses. Reconciling your books is easier when you don’t have commingled expenses, and clean separation is important for minimizing legal liability. After considering several options for business bank accounts, I narrowed it down to a choice between Royal Bank of Canada’s Small Business […]
• People-centered entrepreneurship - Practically all Many of the books I’m reading about entrepreneurship assume that you start with a big idea for a product or service, and then you find and validate the market for it. Many of the people I talk to start with the same assumptions, too. “Oh, I’ve always wanted to start my own business, but […]
• Experience report: Renting a business mailbox - If you don’t want to give your home address out to everyone, a private mailbox (say, one from UPS, not a PO Box) seems to be acceptable for business. To reduce the risk of unwanted visitors, you can incorporate with that mailbox, receive business mail at it, and list it as your contact address. I […]
• Experience report: Incorporating a federal numbered corporation in Canada - This was not at all as complicated as I thought it would be. After twenty minutes, several multiple-choice and fill-in questions, and one credit card transaction, I had my very own company: a federal numbered corporation ($200) with extra-provincial registration in Ontario (free, yay). On a Sunday, no less. The government publishes a guide to […]
• Thinking about how to experiment with business and what I might want to do - “So, what are you going to do?” That’s always what people ask after I tell them that I’m leaving IBM in order to experiment with entrepreneurship. “I don’t know yet,” I say. I explain that I haven’t yet experimented with anything that could be seen as competing with IBM, following our Business Conduct Guidelines – […]
• Getting ready for my next experiment! - It’s been four years of awesomeness at IBM. I’ve: helped companies and communities collaborate facilitated brainstorming workshops with executives from leading companies built web apps in Drupal and Ruby on Rails created popular tools for community newsletters and analyses drawn comics that made people smile across IBM, and learned from and shared with people around […]