Playing Freelance Mode | #163
I recap my freelance journey and answer some questions
December 4th, 2021: Greetings from New York. Hope everyone from the US had a great holiday last week.
🙌 I’ve been having a great time in New York over the past few weeks. I’ve had dinners with new and old friends, met up for coffee with readers from the newsletter, attended shows, and bounced around the city to various friends’ offices and homes. I know the pandemic threatens to linger indefinitely but it feels like I’m living some sort of life again after spending the past 22 months in various states of lockdowns.
✈️After playing with the idea of moving to Miami for a couple of months, we’ve decided instead to move to Austin, TX in January for at least six months. Looking forward to connecting with many of you in that part of the world.
💻 I have one spot left in the early career group coaching experiment I’m kicking off next week. It kicks off Monday at 3 pm EST. E-mail me or put a deposit down here if interested
#1 Freelance Mode & Freelance Questions
I haven’t written much about my freelance work and I thought it might be fun to do a little recap on my journey, the kind of work I’ve done over the years, and the work I’m heading towards in the next year or two.
In the first eight months of self-employment, I pushed aggressively to land freelance projects. This was really the only “game” I knew how to play after quitting my job. In these months I went all-in into what I like to call “freelance mode.” I reached out to everyone I knew and told everyone I was ready, willing, and able to do projects. This is a necessary step if you want to be a freelancer but can be hard because it’s tempting to hedge the insecurity of a new path by continuing to look for jobs.
After 2-3 months of consistent effort, I landed projects that sustained me for about four months. These projects were great and I loved the increased autonomy and flexibility. I had and also found that being a freelancer puts you in a unique position of working directly with the leaders of organizations. This is one of the most underrated things about freelancing - If you are squarely in the “middle” of organizations in your career, it is possible to shift to working at higher levels by becoming a freelancer.
At the end of that stretch, I knew I should go back into freelance mode and build a pipeline of projects, but I leaned in the opposite direction. I started asking deeper questions about work, ones that led to this newsletter and me moving to Asia.
Due to this, my freelance income shrunk and was replaced partially by digital product income but my income dipped for two years. I like to share this chart every once in a while because people seem to find it interesting.
In the last three years, I’ve really been focused on the online course stuff, my writing, and doing projects, often unpaid, that help me learn new things. I still dabbled in freelancing but only taking projects that I was excited about. Some examples:
Writing a report on the future of work for Catalant
Writing a section of a book on remote work culture for Holloway
Coaching a CEO on developing a strategic vision for a Board meeting
Developing a consulting skills training program for a software consulting firm
Working with an Australian tech company, helped them assess whether or not they wanted to enter the US market
Designed a 4-week consulting skills virtual workshop for a US data analytics company
Coached an analyst at a US non-profit firm and did one-off project work
It was fun to continue to do these kinds of projects sporadically but my primary focus was still experimenting with living life not centered around work and doing the creator economy stuff I was getting a kick out of.
Coming back to the US, however, I knew that I needed to make a little more money to continue to live how we wanted and part of me was also excited about leaning into some of the emergent opportunities that were beginning to show up. I genuinely like doing consulting work, it’s just that I never loved doing it 60 hours a week, and even as a freelancer, 40 hours a week is a bit too much. Part-time and project-based, however, I want to do freelancing indefinitely.
About a month before I returned I went back into freelance mode, proactively reaching out to people and sending out signals that I would be open to project-based work again. This was an interesting experience. I didn’t mind it and was kind of excited to explore potential projects. This was in contrast to those early months where I still had the residual frustration with my previous job and deep insecurity of being on a new path. If I had to think about the different phases I’ve gone through in freelancing, there would be three periods:
Stage 1: Desperate to succeed, will take any work within reason (Year 1)
Stage 2: Know what I will say no to, but not sure what I want to do long-term (Years 2-4)
Stage 3: Understanding a couple of areas where I can do great work and am starting to have a coherent perspective and offerings (Years 4-5)
The kind of work I’m talking about in stage three that I’ve found has been working with small and medium-sized professional services firms. This has emerged organically based on some previous project work (I’ve now worked with 4-5 firms like this) and also as higher level work born out of my StrategyU courses.
In the early days, I thought my consulting skills course would be mainly targeted towards individuals, but over time, companies started reaching out, wanting to deploy my training in a more hands-on way. This naturally led to opportunities to pitch consulting work. This past year, I developed a number of “packages” that I display on my site. Now, people know that I offer this higher-level consulting work and I’ve had an increase in people reaching out to me. Here are some examples:
Companies tell me that they love that I list these things publicly and I think this is an argument for more freelancers to proactively develop clear packages and offerings and display them transparently on their site. One of the best examples of this strategy I’ve seen is from a company called NurtureKit, which offers consulting and coaching on how to use ConvertKit. His pricing sends three different signals to three different kinds of clients:
Back to my work, my current pipeline looks like this:
Exploratory conversations or e-mails (2): Boutique executive search firm, insurance strategy group
2nd/3rd Conversations (6): Strategy group in UK, gig economy staffing firm in US, Consulting firm in the US, finance strategy group in the US, Canadian marketing consulting firm, and Boston-based advertising consultancy, a US tech company starting a strategy group about potential project-based staffing
Sold! Kick-off in January (2): Running virtual consulting skills workshop with UK consulting firm, working with Nigerian consulting firm on strategy & analyst coaching
Completed (1): Ran workshop for marketing consultancy on building a high-performance consulting process
If you know anything about freelancing you know that many of these may never turn into anything or may lead to something in the distant future. My experience in winning projects has been that they either happen very fast, within a week or happen after a large gap of time following an initial flurry of conversations.
Will freelancing be my primary mode of making money in the future? I’m not sure. Freelancing is something that always changes and this is part of the fun. I can change my “job” or work much faster than I could in full-time work, which solves a major issue I always had with my previous path.
The digital products, courses, and coaching I’m doing are still things I’ll work on but I’m just never sure where those are headed. I don’t want to double down and go all-in on those either. For now, I like the portfolio approach and the wide range of things I am working on.
Some other questions about freelancing that people had:
What work do you actually do?
You can click through to the virtual workshops I do and see what kind of things I offer but if you want to get a flavor of the more research-based work I’ve done in the past, here are 10 hours of research on the steel industry for an investment firm.
Most of the other stuff I’ve done I can’t share, unfortunately.
Which kinds of work give you energy and which feel routine?
To me, project management of initiatives in large organizations feels routine in the sense that I’ve been in that mode hundreds of times in consulting projects in the past. I know exactly what needs to be done and how to do it but I just don’t enjoy navigating things like politics, stakeholder management, and so on. So I try to avoid this kind of work.
I’m quite energized by working with a hyper-curious client, ideally in a leadership position, who is excited by asking hard questions. It’s even better if I can pair this with hands-on coaching and working as part of a front-line team where I can help others improve and add value to the work they are doing.
I also love the workshops I’ve been running for my course with organizations.
If there was some way to measure mental status at different stages of your journey?
From the above:
Stage 1: Desperate to succeed, will take any work within reason
Fear, insecurity, impostor syndrome, excitement, growth & energy, momentum, success
Stage 2: Know what I will say no to, but not sure what I want to do long-term
Uncertainty, shame of not earning money, contentedness, curiosity, fear of taking projects I’ll hate
Stage 3: Understanding a couple of areas where I can do great work and am starting to have a coherent perspective and offerings
Excitement, some fear of overwork, pressure to make money, curiosity, amazement at the # of inbound requests, uncertainty of where this work goes
What unfair advantages could you press on?
I genuinely love coaching and working with people and helping them develop skills. Whenever I can demonstrate this ability, I have a much higher likelihood of landing projects. I am still brainstorming on how to make an upfront coaching offer free or low-friction to organizations such that it can be the first phase of a project.
Generally, I think it can be hard and take years for freelancers to figure out the kind of work they love doing. For me, it’s probably always going to shift but it took a solid 3-4 years until the kinds of clients I wanted to work with both knew about my work and were regularly reaching out to me. This is something that many new freelancers don’t like to hear. There does seem to be an inevitable initial period where people need to take projects that aren’t perfect as a way of slowly figuring out what not to do.
What % of rev came from referral vs outgoing effort?
Right now I have one potential project that came from a referral. Two potential projects are based on outbound effort in my personal network and the remaining majority are from inbound requests from my StrategyU content (YouTube, blog, newsletter).
While this is inbound, it still morphs into me needing to make consistent outbound efforts to turn these into real projects.
+Have more questions? Happpy to answer them. Also, I have a freelance skills course if you are interested. I’m offering $50 off until the end of the year.
#2 Beginning of Infinity
I just started David Deutsch’s Beginning of Infinity. The beginning really captured my imagination and made me want to read more. I’m copying the rest of the intro here. If you want to join me in reading it over the next month, let me know.
Progress that is both rapid enough to be noticed and stable enough to continue over many generations has been achieved only once in the history of our species. It began at approximately the time of the scientific revolution, and is still under way. It has included improvements not only in scientific understanding, but also in technology, political institutions, moral values, art, and every aspect of human welfare.
Whenever there has been progress, there have been influential thinkers who denied that it was genuine, that it was desirable, or even that the concept was meaningful. They should have known better. There is indeed an objective difference between a false explanation and a true one, between chronic failure to solve a problem and solving it, and also between wrong and right, ugly and beautiful, suffering and its alleviation – and thus between stagnation and progress in the fullest sense.
In this book I argue that all progress, both theoretical and practical, has resulted from a single human activity: the quest for what I call good explanations. Though this quest is uniquely human, its effectiveness is also a fundamental fact about reality at the most impersonal, cosmic level – namely that it conforms to universal laws of nature that are indeed good explanations. This simple relationship between the cosmic and the human is a hint of a central role of people in the cosmic scheme of things.
Must progress come to an end – either in catastrophe or in some sort of completion – or is it unbounded? The answer is the latter. That unboundedness is the ‘infinity’ referred to in the title of this book. Explaining it, and the conditions under which progress can and cannot happen, entails a journey through virtually every fundamental field of science and philosophy. From each such field we learn that, although progress has no necessary end, it does have a necessary beginning: a cause, or an event with which it starts, or a necessary condition for it to take off and to thrive. Each of these beginnings is ‘the beginning of infinity’ as viewed from the perspective of that field. Many seem, superficially, to be unconnected. But they are all facets of a single attribute of reality, which I call the beginning of infinity.
#3 Events
Shoutout to Nikhil Krishnan who hosted an awesome event in Brooklyn last night where people gave talks on random topics. He’s got a fantastic newsletter on the future of healthcare that’s also worth checking out.
I also met another reader and fellow solopreneur, David Nebinski, who I joined on his podcast about a month ago about people with portfolio careers. Check it out here.
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