Career Transitions and the Ladder of Legitimacy
💌 The Roundup // 003
Friends–
Thanks, once again, for all the thoughtful feedback on last month’s issue. I liked learning about your productivity regimens. If there’s anything you’ve implemented that’s been impactful, I’d love to hear about it.
If this is the first issue you’re seeing, it either means we just met in the past month (👋) or I forgot to include you previously (sorry 😔). To get a sense of what this is all about, you can check out previous editions below.
With that, let’s get on to the good stuff.
Career Transitions and the Ladder of Legitimacy
By their nature, career transitions tend to involve a lot of self-centered thinking.
What do I want to do with my life?
What will make me feel fulfilled?
Questions like these are important, but, they only solve part of the problem. On the other side of any career transition there exist one or more people who must agree to take on the risk of a junior hire. To land a dream job, you’ll need to understand how these stakeholders think about risk so you can plan the steps of your transition accordingly.
When coaching Tradecraft members through career transitions, we try to get them to think like their future employers. For companies, hiring is a pain. Valuable team members must devote hours of time to interviews and hiring committees, instead of revenue-generating activities. Once a hire is made, more time must be spent training and orienting the newcomer. If the hire doesn’t work out, the company will need to pay severance and deal with ramifications of the hire’s poor performance. In total it represents a good deal of risk for any employer.
While the whole company shares in this risk, the hiring manager often bears the largest share. A manager’s performance is judged on the output of his team and a bad hire can significantly drag down that output. Since a poorly performing team can limit the manager’s career growth, hiring managers tend to be naturally risk-averse.
Since it’s hard to know whether a team member will work out, most hiring managers cover their asses by hiring candidates with obvious signals of legitimacy. That way, if a hire doesn’t work out, the hiring manager can say, “well, who’d have thought that someone who worked at Google would have been such a bad fit?” In the vein of the oft-cited saying that “no one ever got fired for buying IBM,” no one ever got fired for hiring from Google.
New hires can represent several different types of risk, including:
Functional risk– Can the candidate accomplish the objectives of this role?
Stage risk — Does the candidate have experience operating in a work environment like this one?
Culture risk — Will the candidate’s values, attitudes, and habits mix well with the other people on this team?
Customer risk — Does the candidate have experience solving problems or creating solutions for our customer?
Problem risk — Has the candidate created solutions to solve this type of problem before?
Solution risk — How comfortable is the candidate with the process of building and selling this type of solution?
The way most hiring managers see it, the least risky employee is one who has done the exact same job before, in as similar of a context as possible (note that I don’t believe this is the right philosophy).
To understand how much career transition risk you’re taking on, ask yourself how much hiring risk your future manager will need to bear. The more elements of your job you try to change from one opportunity to the next, the more that risk will grow.
What to do about it
You have two levers at your disposal to deal with transition risk:
Offer more
Ask for less
To offer more you’ll either need to expand the abilities you can share with your employer, or the time you can devote to work. In my experience, most transitioners understand the value of this lever. They believe that by spending enough time building skills or demonstrating their dedication, an employer will give them a shot. While, of course, this is an essential part of any transition I think it’s lever #2 that’s underrated.
Ultimately, the catch 22 of any career transition is that hiring managers want to see that you have experience doing the job, which you can only get through a job offer. So, how can you convince employers to give you a shot, in the first place?
By asking for less.
In practice, this means making a smaller ask from your prospective employer. This might mean you initially lower your hourly rate or even offer to do work for free. Rather than trying to get for a full-time job right away, you give employers the chance to try you out before making a long-term commitment. As you gain more experience you can then ask for a bit more. I think of this as climbing a ladder of legitimacy. To illustrate how it works, let’s look at a case study.
Michelle is an architect who dreams of landing a product design role at Slack. In her current role, she represents almost every type of risk to her future employer. She has no experience with Slack’s customer, problem, or solution. Furthermore, her architecture firm is small, has grown slowly, and has a very different culture from Slack. While Michelle does have a functional skill set that crosses over with digital product design, she hasn’t used it to create software products. Given all this, it’s unlikely Michelle will be getting her first offer from Slack. But that doesn’t mean she can’t get there eventually.
Assuming Michelle has the intellect and motivation to build the skills she needs, let’s look at how she might climb the ladder of legitimacy to mitigate some risk for her future employer.
Step #1: Contribute to a project for free
This allows Michelle to get her hands dirty and start gaining experience. She’s mitigating some hiring risk by involving more experienced people and working for free. While it may seem like a small ask to contribute to a project for free, she’s asking both the other contributors and the client to entrust her with sensitive information and time.
Step #2: Lead a project for free
She’ll now need to demonstrate that she can make the rest of her team look good by delivering a quality work product in a timely manner. In selecting which projects to work on, she may want to consider projects at companies that share a similar problem, customer, or solution to Slack.
Step #3: Get paid for project work
Michelle isn’t yet asking for a short term role. Just a single project. The difference this time is that she’s looking to get paid in return. This might be the hardest step of Michelle’s ladder. If she’s unable to find the right opportunity Michelle can:
Offer a money-back guarantee
Ask for a lower rate
Downscope the size of the project
Bring other members on the team with more legitimacy
Step #4: Land a short-term contract
Michelle’s now looking more serious responsibility in return for ongoing payment. While the contract is limited which means the client doesn’t need to worry about paying severance if things don’t work, it’s certainly not without some risk. If Michelle’s having trouble getting traction at this step, she can always lower her hourly rate. Again, this will be a great opportunity to look for a company with some similarities to Slack.
Step #5: Get a full-time role
While this may seem like the top rung of the ladder, Michelle may still be a ways off from her ideal role at Slack. First, she may need to take a chance on a lesser-known company or a larger employer that’s lost its luster.
Step #6: Land your dream job
Assuming Michelle has kicked ass at her last company, and gained some relevant experience, she’s now in a much better position to go for that dream job. Keep in mind, if the company is really hot (let’s say Slack in 2016, or a company like Opendoor today) she may be looking at a few more rungs between #5 and #6.
Conclusion
While this may seem like a lot of added steps, climbing one rung at a time will ultimately get you to your goal faster. Instead of spending your job search waiting for emails to be returned while watching your bank account dwindle away, you can start gaining experience and income much sooner.
You can also speed these steps up. For example, no one says that your first full-time role needs to last two years. One year, or even six months, may allow you to level up to a more desirable role. You can also speed things along by combining steps. By taking two part-time roles or more than one project, you can build momentum and confidence that will help propel you to your next opportunity.
Career transitions can be a humbling experience. If you’re used to being sought-after by employers, their new-found apathy will likely feel demoralizing. Instead of setting yourself up for the inevitable rejection that comes from changing every part of your job at once, try making a series of smaller changes. Ultimately you’ll be able to regain your former career capital by climbing the ladder one step at a time.
Endnotes:
A permalink to this post can be found here
Content Recommendations
How to Be an Effective Executive
(17-minute read)
Founders and investors have lots of great role models who write about their craft. Unfortunately, despite the number of great operators in the Valley, too few share their secrets for how they operate large teams at fast-growing companies. One of the best people to pay attention to on this topic has to be Founders Fund investor, Keith Rabois.
Rabois launched his career at PayPal where he oversaw several functions as an Executive VP, then went on to take executive roles at both Linkedin and Square, and co-founded the fast-growing startup, Opendoor. With that said, if anyone knows how to operate as an executive it’s Keith.
Here are some of my favorite nuggets of advice from Delian’s article about Keith:
Managers are judged based on the output of their team, divided by the number of people they needed to achieve it. So, make sure that any hire either raises the average productivity of the team or is a multiplier that increases the output of everyone on the team.
Managing people according to their output incentivizes employees to tackle short-term conservative projects that they know succeed. They may miss the experiments that could lead to unexpected outsized wins.
Avoid having team-members over-optimize for a single metric by pairing indicators. For example, by paying salespeople only on contract value, they may be incentivized to close customers who will churn. So pairing a revenue metric with a churn metric can be a good way to align incentives.
If you like this, I’d suggest you check out the Delian’s other essays documenting his learnings from Keith:
The Future of Geopolitics
(1-hour watch)
In the past two weeks I’ve gone down a total rabbit hole on Peter Zeihan’s vision of the future of geopolitics, which is at once both frightening and fascinating. Here’s the broad outline:
Since the end of WWII, America has used its navy to promote free trade amongst its allies, leading to unprecedented peace and prosperity. However, since the fall of the Berlin Wall, our commitment to ensuring the global order has been slowly eroding.
America’s pullback will lead to a disastrous decline in standards of living for those countries that have become reliant on global free trade (spoiler: that’s most of them).
The fate of these countries will, once again, become subject to their geographic features and demographic makeup, which for most are quite unfavorable.
The U.S. will largely avoid this decline due to it’s:
Lack of reliance on global trade
Energy independence (stemming from the shale boom)
Relatively young demography
Relative ability to assimilate immigrants (also helpful for demographics)
Geographic insulation from most other countries
High-quality agricultural land
Military supremacy
He also lists a handful of other unlikely countries that will ascend in this new world order (hint: it’s not who you think).
I’m no expert on geopolitics. So, I can’t be sure how accurate his predictions are. But if your life has any connection to the world outside this country, you owe it to yourself to listen to this talk. If you want to continue down the rabbit hole, he’s got two books and is coming out with a third later this year.
Stubborn Attachments vs. The Vulnerable World and Fermi’s Paradox
(14-minute read)
I hate to say it, but over the past few months, I’ve been turning into more of a pessimist about technology, and its role in humanity’s future. That’s thanks in no small part to Jeremiah’s criminally underrated blog, We Are Not Saved.
This post contrasts the thesis of economist Tyler Cowen’s latest book, Stubborn Attachments with futurist Nick Bostrom’s paper, The Vulnerable World Hypothesis. For those who aren’t familiar with the book, Cowen essentially argues:
Our top moral priority should be preserving and improving humanity’s long-term future
The way to do that is to maximize the rate of sustainable economic growth
We should respect human rights while doing so.
I naturally gravitate toward Cowen’s view. However, Bostrom’s Vulnerable World Hypothesis made me think again. He analogizes discovering new technologies to drawing balls from an urn.
Drawing a ball from the urn represents developing a new technology (using a very broad definition of the word). White balls represent technology which is unquestionably good. (Think the smallpox vaccine.) Off-white balls may have some unfortunate side effects, but on net they’re still very beneficial, and as the balls get more grey their benefits become more ambiguous and the harms increase. A pure black ball represents a technology which is so bad in one way or another that it would effectively mean the end of humanity. Draw a black ball and the game is over.
There are only a handful of ways humanity can avoid drawing a black ball:
We stop drawing balls
We keep drawing balls, but there are no black balls in the urn. There is no technology that will irrevocably end humanity
Growth fixes everything, even the existence of a black ball
We keep drawing balls, but we implement draconian measures to prevent black balls from truly “ending the game”
I agree with the author that the first seems nearly impossible. The second and third seem too risky, given the odds, that I wouldn’t be willing to bet the future of humanity on it. That leaves a strong argument in favor of #4.
Assuming our goal is still to perpetuate the survival of humanity, I’m starting to think that we will need to start shifting our values away from ones that lead to thriving and happiness to ones that lead to survival. Does this mean a surveillance state, like the one China is building, will be necessary to get us through the turmoil to come? I don’t know, but I’m certainly more open to the idea than I was a few months ago.
As I mentioned, I’ve been really enjoying reading and listening to this author (he makes podcast episodes from each post he writes). To get a better understanding of his world view, I’d suggest starting with this post.
Time Use of Remote vs. Non-Remote Workers
(3-minute read)
Let’s end with something lighter. Shall we?
From my last newsletter, you may have caught on to my fascination with time, and how people choose to spend it. Given the growing popularity of distributed teams and remote working, I’ve been interested to see how the lives of these employees differ from traditional office-workers.
Here are some of the more interesting things I learned from the post:
As of 2016, about 27% of full-time workers did at least some work outside of the workplace. That’s up from 23%, in 2006.
Non-remote workers spend a median of 35 minutes traveling (versus remote workers who spend zero minutes). That means switching to a remote job should save you about 8.87 days, over the course of a year.
Remote workers tend to work less in terms of median number of hours (7 hrs. 47 mins. vs 8 hrs. 20 mins). However, there are a lot more remote workers that work under 100 minutes and over 700 minutes per day.
The author has produced several other amazing data visualizations breaking down:
They’re all short posts with amazing visualizations (like the one below). Definitely worth checking out.
Community
If you’re hiring, share some info about what role you’re looking to fill, and I’ll try to pass it along to the right people.
If you’re looking for your next thing tell me a bit about what kind of role you’re looking for, and I’ll keep my eyes peeled for interesting opportunities.
If you want to grab coffee with someone in a similar role, let me know and I’ll try to match you up with a peer.
Lastly, a special thanks to my fiancée, Ash for her help with copyediting. Any coherent sentences can be attributed to her. As always, if you have any thoughts, I’d love to hear them.
Until next time,
Nick