the five pillars of intentional career advancement

for traditional and non-traditional careers

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Hi Cece, I am curious about how you manage your time, energy, and projects when it comes to pursuing a non-traditional career path/self-employment. I admire how you are pursuing so many endeavors, but I can imagine it is not easy to handle. Do you have advice for those of us who are also interested in building a career consisting of many different parts, rather than something more linear/direct? Thank you!

- Annie

Great question, Annie! Did you know I actually hated the idea of a non-traditional career when I was in my early twenties? I wanted to be One & Done in all avenues of my life—marry the first suitable person who also wanted to marry me; work my way up in a profession and company with a clear linear progression; put together a perfect capsule wardrobe that I’d never have to update again. The fact that I now have a non-trad, portfolio career—a mix of writing, creating content, and practicing law—isn’t so much a testament to how much I’ve changed but discovering that even seemingly linear careers are not so linear.

Case in point: doctor is perceived as one of the most stable, most linear careers. You go to med school, do your residency, maybe a fellowship, and then apply to jobs. Sounds straightforward, right?

The devil lives in the details. After years of following a blueprint, doctors are confronted with a deluge of considerations about what “being a doctor” looks like in practice. Will they join a group physician practice, hospital, health system, or academic medical center? Will they be paid a fixed or variable compensation? How long will they be guaranteed employment (as long as there isn’t a breach of their physician employment contract)?

Recently, when I tried to make an appointment with one of my doctors, I found out her entire office was closing. None of the staff knew what was happening; my doctor didn’t know what was happening. And because of the non-compete in my doctor’s contract, she couldn’t let her patients know where she was moving to. I had to independently find her and finagle an appointment to see her. (She technically wasn’t seeing patients anymore for the area of medicine I’d previously seen her for). When I asked her what happened to the old office, she told me she didn’t have much more notice than I did about the whole operation shutting down.

How stable! How linear!

The same is true in Biglaw: I’ve heard so many stories of associates fully expecting to make equity partner, only to not, and longstanding non-equity and equity partners being pushed out of firms. Adaptability is becoming more and more a necessity, rather than a nice-to-have. Gone are the days when you summer at a firm and can reasonably anticipate equity partnership at the same firm.

My linear (and admittedly naïve) expectation for law firm life had been this: bill ~2000 hours a year, do it for ten years, make equity partner. Unfortunately, I discovered doing that wouldn’t put me in a good position for promotion. I would be in an okay position—I wouldn’t get fired—but I’d be leaving my promotion prospects largely up to chance and the whims of others.¹ And if there’s one thing I hate, it’s ceding control.

So I took matters into my own hands. Not only did I do my legal work—the “linear” work—but I added several other areas to what constituted “work,” as well. Even in the linear path of law firm associate → partner, I needed to juggle the following endeavors:

1. Billable hours (the “linear” work)

2. Training & learning

3. Internal networking (existing partners have to vote to admit you into the partnership, and they can’t do that if they don’t know who you are!)

4. Sales (client/business development and external networking)

5. Giving back (e.g., mentoring)

Having to juggle between these five facets in a traditional career was my gateway to eventually juggling between multiple pursuits in a non-traditional career. It made the transition easier, too—because I already had experience with, and a framework for, envisioning “work” in the expansive, holistic sense demanded of non-trad/entrepreneurial/self-employed labor.

My five pillars of “work” in Biglaw translated quite nicely to my current mode of work:

1. Billable hours → Money to pay my rent/bills

2. Training & learning → Still training & learning!

3. Internal networking → Networking with other writers, creators, entrepreneurs, and those with non-trad careers

4. Sales → Building my ideal career

5. Giving back → Still giving back!

More on each below.

Billable Hours → Money to Pay My Rent/Bills

This is the baseline expectation for whatever work you’re engaged in. In a corporate setting, these are usually spelled out for you, and if you’re junior, these are the tasks that your boss(es) will assign to you. Do what you’re told; do it well. Schoolwork, essentially.

In a non-trad career, Money to Pay My Rent/Bills is less straightforward. You can, theoretically, do anything to earn money. Oftentimes, what you want to be paid for will be at odds with what the market is readily willing to pay you for. (But it’s not because what you have to offer is valueless! It’s simply a reflection of the market not knowing what to make of non-trad offerings.)

To use myself as an example: because of my pedigree and past work, I can readily earn money doing legal work or admissions consulting. If my goal were to simply maximize revenue, I should be spending all my working hours on legal work or admissions consulting. BUT! I don’t want to. Doing so would vitiate the whole point of having a non-trad career.

Instead, I figure out how much money I generally need to earn in order to pay my rent and bills, and I aim to do only as much legal work to meet that requirement. If demand for my legal services dries up, I’ll look into admissions consulting, or coaching, or whatever—the point here is to meet the market, but only as much as I need to in order to live and work another day.

Training & Learning → Still Training & Learning!

This should always be the fun part. You get to follow your curiosities about your work! In law, I’d read newsletters on privacy developments, generative AI lawsuits such as New York Times v. OpenAI, and talk to partners about what they’re seeing in the legal market. And because I was consistently drawn to discussions about one subject matter—law and technology—over news in, say, M&A or class actions or securities litigation, I knew which practice areas were suitable for me. If the Training & Learning in whatever you’re doing feels painful or boring, it’s a good sign you’re in the wrong domain and need to move onto something that truly sparks your curiosity.

Nowadays, I still follow generative AI developments and the Biglaw market with great interest—because I like writing about technology and Biglaw—but you’ll also find me clicking on media and social media gossip, publishing industry talk, and storytelling and editing advice. I take writing workshops and read craft books on writing, storytelling, entrepreneurship. And I also go to therapy and do waaaay more self-reflection than I used to—because a non-trad career requires that you also learn about yourself. No boss is going to tell you what to do next, so you have to figure it out!

Internal Networking → Networking with Others with Non-Trad Careers

In the corporate sphere, internal networking served two purposes: (a) increasing visibility across groups and functions; and (b) finding colleagues who can offer emotional support and mentorship. Networking in a non-trad career isn’t much different.

Because humans and work both benefit from socializing, networking within a non-trad career is still of paramount importance. It’s helpful to be able to think of others—and for them to think of you—as you go about your non-trad career paths, whether it’s for referrals, recommendations, or simply commiseration over how self-employment sucks sometimes. I’ve found much solace and support in others embarking on non-trad paths, as well as inspiration—because it is inspiring to see so many people try to carve their own way through life! And as lonely as having a non-trad career can feel, many people actually have non-traditional careers. (The hard part is finding them.)

Sales → Building My Ideal Career

In law, I saw that the partners who built their own books of business with clients they wanted to help tended to be happier than the partners who were less intentional about their clients (and lowkey hated some of them). Intentionally building a client base, however, is harder than saying “yes” to whatever comes your way. You’ll also receive a lot more “nos” than peers who don’t pitch as often or as intentionally. But pitching—putting yourself out there, opening yourself up to rejection—is a necessary component of aligning salesmanship with self-fulfillment. For what is worthwhile business development if not bending your reality towards your ideal?

In self-employment, this pillar involves working on projects which may not be paying off now, but if they did in the future, you’d be one step closer to the career you want to have. For me, these projects include works of fiction, screenwriting, interviews, and this newsletter! Do they financially justify the time I put into them right now? No—but if I were a Biglaw partner, neither would every pitch. And because I have adequate Money to Pay My Rent/Bills from the first pillar, I can ease pressure off these passion projects to provide for me financially—and just enjoy them.

Which isn’t to say every part of Building My Ideal Career is enjoyable. All jobs—jobs you hate and jobs you love—will have parts you hate and parts you love. As a lawyer, I hate modifying contracts which are largely based on templates. (I find it intellectually boring.) As a writer and content creator, I hate posting on social media. (Really.) I have a friend who’s CEO of his own tech startup, and he spends 40% of his time on HR, Payroll, Marketing, and all the stuff he doesn’t want to do. But as long as you’re spending most of your time doing what you want, that’s pretty good.

Giving Back → Still Giving Back!

I’m a firm believer that giving back should be a permanent component in anyone’s career. This can take on several varietals—direct mentorship, volunteering, community organizing, increasing transparency, etc.—but you should keep on helping others navigate this wild, crazy world as you yourself figure things out.

I used to accept all informational interview requests when I was a junior associate, but as I got more senior (and more popular on social media), that became untenable. One of the hardest parts of giving back in a non-trad career is dealing with the assumption that because you work for yourself, you have more time to meet one-on-one with others than, say, an investment banker or doctor or Biglaw associate. As a result, I’m sure I disappointed others more frequently. That fact pained me at first—I had a lot of guilt over it, both internally and externally—but therapy (see Training & Learning) and powwowing with other career creators over this shared guilt (see Networking) helped me better come to peace with my boundaries.

Now the overarching question: how do you juggle between these five pillars? Apart from Money to Pay My Rent/Bills, which I need to accomplish in order to not get evicted, I have an impromptu approach to the rest. At the beginning of every week, I do what I’ve always done, even in Biglaw—I time-block out my upcoming week, take a look at what’s missing, and then figure out how to make time for those pursuits. Some weeks are heavy on 1-2 pillars and light on the others—but on a quarter-to-quarter basis, it tends to balance out. Striving for daily balance is a pipe dream—but in letting that impossibility go, I’m able to more meaningfully pursue other dreams. ◆

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1. To really put myself in the best position for promotion to equity partner, I’d have to either (a) build a book of business that generates in revenue approximately 3-5x my desired annual compensation or (b) build a relationship with an equity partner who will then hand me their book of business upon retirement (which would need to be carefully calibrated to my desired timing for promotion).