“The three most harmful addictions are heroin, carbohydrates, and a monthly salary,” Nassim Taleb once derisively wrote about anyone opposed to professional risk. Sabre-rattling aside, it’s hard to deny that our economy (and along with it, our jobs) have shifted – exemplified by the proliferation of side projects, gigs, free-lancing, consulting, and free-agents. For some it’s a search of autonomy and freedom while for others a way to learn new skills – often time in pursuit of finding meaningful work.

When we think about ditching the paycheck economy, the freelancer comes to mind. They have skills and they “trade” their time for income. But what should you do if  you’ve just quit your corporate job, unsure about the specificity and transferability of your skills? What does the path to working for yourself look like? And does the loss of a corporate affiliation jeopardize your ability to establish yourself as a thought leader, join professional organizations, and advise startups or policymakers?

You don’t have to skim far down April Rinne’s LinkedIn profile to know that the answer is an emphatic NO. The first half of her career was in economic development and micro-finance. But her insatiable wanderlust has led her to over visit 100 countries in her lifetime and work in 20 countries just last year.

Eight years ago, she became a “career portfolioist” and developed an expertise in the sharing economy, the future of work and global citizenship. I spoke to April on the Rad Awakenings Podcast about how she prototyped and iterated her way into independent work, how she identifies and dives into nascent fields, and her (surprisingly low) risk tolerance.

1. Hit the pause button

Our professional culture is obsessed with “doing.” If we aren’t moving the ball down the field, we’re nothing. If we’re not growing, we’re falling behind. But did you know that when you sleep, your brain activity only declines by 20%? And in the same way sleep enables us to cross-pollinate ideas and expand our thinking, a pause (or a firm do not work window) is what we need most, particularly if we have a bit of financial resources. Rinne warns about hopping too quickly into the next thing:

[su_quote]I strongly encourage people [taking a sabbatical or making career pivots] to have a period of time where they have not finished one thing Friday and start their next thing Monday. Spend some time looking at those bigger life goals, looking beyond what’s going to be on your CV or the headline of your LinkedIn profile. Spend some time with the multi-faceted question: Are you professionally on the life path you want to be on and, if not, how can you actually embed this into a professional change. I’m always amazed by how this idea never enters people’s mind, or it does, they steamroll it out of existence because it doesn’t relate to what the next business model’s about. [/su_quote]

2. Take an inventory of your skills

During this pause, it’s so critical to reclaim, then rediscover your career narrative. Personally, when I quit I had skills in finance and loved tech. The narrative became that I had to do FinTech. But that was missing the point on my higher level skills (mentoring, relationship building, communication) and unknown ways in which I knew I wanted to grow as a professional – and human. April discusses how an unrelated online course or a trip (but not a vacation) could widen your own perspective.

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Use a pivot as a way of learning new skills. And here I’m not talking IoT (i.e. internet of things) or “I’m a marketer and want to learn about operations.” How can you get a different flavor of perspective? It could be enrolling in a course that’s unrelated to what you do or taking a trip – and I have to be very clear here, not taking a vacation, but instead treat it as professional development.

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3. Make a calculated bet, with guardrails

Believe it or not, April is not a particularly risk-seeking individual. And if you have some savings, it doesn’t have to be too risky (and no, you won’t end up broke). For me, my plan was twofold: first, I made an angel investment in myself by setting aside an amount that, as a family, we were comfortable going to zero (and this spreadsheet can help). And you’ll notice that I deliberately used the phrase investment (in myself) as opposed to spending. Next, I matched that with my COBRA (i.e. Health insurance) coverage, which lasted 18 months. So 18 months became my window. April set up her “parameters of the sandbox” or “guardrails” through a conservative set of assumptions:

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On one hand, I’m pretty risk averse which seems contradictory to going independent. In the initial phase I knew that there wasn’t going to be a guaranteed source of income. I had savings and was looking at it more through the lens of “look it matters to me to try this” and if I don’t figure it out within some months, then we’ll try something else. It was absolutely not willy nilly, I thought long and hard about this, I had my financial plan in place (with some flexibility). For me it felt scary, but I knew I had done my homework.

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Once the parameters were set, it truly enabled her to focus on this new career phase. April’s husband helped push her on this by saying:

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“Just try it. You don’t HAVE to do this!” Set yourself a time limit, say 6 months or a year, then THROW yourself at it – blood, sweat and tears, sweat equity, you name it. Go for it and don’t second guess yourself during this time. That way you won’t spend 50% of your time stressed about whether you made the right decision. And then 6 months or a year later, rise up and ask yourself “Was this worth it or not?”

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And here’s the crazy thing. Often times the biggest risk is what you choose not to do – if there’s a voice in you saying “you have to do this,” ignoring this may be the riskiest strategy. Jeff Bezos calls this the regret-minimization framework. For April, regret-minimization was, in part, influenced by the death of her parents:

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The element of “screw it” came from doing what I wanted to not regret in my life, so there was this sense of “hell yeah, I’m going to try” but with guardrails or “parameters of the sandbox. Because on your deathbed there are certain things you may regret doing but there are other things I would regret NOT doing this. And for me it was driven by “I don’t want to regret not having tried.”

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4. Dive into a nascent space

I’m not def not one of those bitcoin-obsessed-bros. But I think it’s a really interesting and promising technology. And while I have zero fucking clue as to whether it will make a good investment, here’s a stat that mesmerizes. In speaking to Fred Ehrsam on the Rad Awakenings Podcast (co-founder and former CEO of Coinbase) we discussed how bitcoin came into existence in 2009. Assume you dove into bitcoin (for a year) at the beginning of 2018. By the end of 2018, you’d have been involved in the space for 10% of it’s entire existence! And again, forget the investment virtues (or lack thereof) of bitcoin, there’s a good chance that it’s a transformative technology. I can’t think of another space with so much potential in which a year can get you that much experience.

April made this bet with the sharing economy 8 years ago:

[su_quote]I’ve always liked to get into ideas when they are really, really nascent. I got into microfinance way before the Nobel Peace Prize, before it was a household term and before it was viewed as a bonafide tool for economic development. I was enjoying my career, but not leveling up as a professional. That’s when the term “the sharing economy” came up and I said to myself, “THAT has potential for the planet as well” in terms of inclusive responsible business, Community Building, were things I had seen in microfinance.[/su_quote]

So during this exploratory window, she dove in – head first. And you know what, in challenging the status quo, having people tell you that you’re crazy can be a positive indicator:

[su_quote]I threw myself headfirst into this space called the sharing economy where people didn’t know what it was. People looked at you like you were kinda crazy. But I said, I’m going to make a bet on this space, I think it’s going somewhere and I’m going to carve myself an interesting professional path. [/su_quote]

[su_quote]I share this because I didn’t know how it was going to look, I didn’t have the business model figured out and I ended up saying “I’m going to give myself a year, check-in in 6 months” and within that year, enough took root for me to say “I know I’m onto something.”[/su_quote]

And this is how you get a crack at “expertise” in this rapidly changing economy:

[su_quote]Seven years later, I realize that I was able to ride that wave because I got into the space at a time when it was so nascent and everyone needed help unpacking what was what. And within a few months, I was working with companies, writing some of the earliest pieces that I know of around policy for the sharing economy.[/su_quote]

5. Make sure you regularly ‘shed your skin’

Axios recently ran a piece titled The next great challenge, 100 year careers, in part inspired by the scientific research stating that somebody born today has a chance of reaching the age of 150. Thus it’s possible that we’ll work til were in our 80s, or even later.

This feels sensational and click-baity, but there is a double trend at play here. Yes, we are probably going to be working longer all while technological innovation is shortening the relevance of our skills. Thus reinventing yourself is absolutely critical. April dubbed this “shedding your skin” and the metaphor is so powerful:

[su_quote]I’m also keenly aware of the fact that a concept like [the sharing economy] is not what you do for the next 50 years. At some point, the sharing economy is just the economy. There’s this constant sense of shedding a skin, reinvention and leveling up. For me, it goes back [to the fact] that there are still so many skills that I want, but don’t have. And there are many, many issues and topics that need help. Topics that I find fascinating.[/su_quote]

And this learning is inter-disciplinary, oftentimes not found in books, and requires a ravenous curiosity:

[su_quote]I use the example of concentric circles. Every few years I need to expand to another concentric circle. So what I’m doing before (i.e. the sharing economy) is not the only thing I do, nor would I want for it to be. Now I’ve got embedded circles of “the future of work and the sharing economy” or “citizenship and the sharing economy.” There’s definitely a nexus there.[/su_quote]

6. Let emergence kick in

Unless you’ve experienced it, emergence is one of those hard-to-define terms that come across as corporate woo woo. So I won’t try, other than to say that it comes from a combination of trust, creativity, open-mindedness and work ethic. Once those seeds are planted, you sit back (well, sort of) and see what blossoms.

[su_quote]When I decided to make this leap years ago, emergence was not a term that I would’ve been in my vocabulary. Emergence is fundamental to what I do and how I even see my path. It’s important to note that this has not been an instance of “I made this bet, and it all worked out!” No. This has required lots of leaps of faiths. This is up and down. Ebbs and flows. I happened to pick a concept that did take off, in wonderful ways.[/su_quote]

7. It’s not the be-all, end-all

We’re always in search for a grand and unifying theory about what the perfect job looks like. But it’s important to remember, that like most things, there are trade-offs. And that with time, your preferences will change. The importance is keeping an open mind:

[su_quote]I love being independent. Right now. I’ve never looked at it as the holy grail. I look at this as one chapter in my book of life, I loved the chapter I’m writing, but I’ve never ruled out [a more traditional role]. At the end of the day, there’s a set of trade-offs. There are days when I say, “wow it would just be so much easier [to be in an organization]” but then remind myself that I love the path I’m on and wouldn’t change the bundle for anything. But back to emergence, I don’t know what’s going to arise on the horizon and I’m going to be open with as much peripheral vision as I can.[/su_quote]

So there you have it, a blueprint for those looking to pivot into an unbundled career. And there’s a commonality amongst these steps – they’re a manifestation of what Seneca once said: “Luck is what happens when preparation meets opportunity.”

You may enjoy

 

• How to survive a career transition
• Why are successful people so scared of being broke
• The unbundled career
• Venkatesh Rao on the ‘free-agent economy)