Unlocking Optionality in Your Career

What options are available outside of full time, in-house employment?

Hi there, it’s Adam. 🤗 Welcome to my weekly newsletter. I started this newsletter to provide a no-bullshit, guided approach to solving some of the hardest problems for people and companies. That includes Growth, Product, company building and parenting while working. Subscribe and never miss an issue. Listen to my new podcast about fatherhood and company leadership - Startup Dad. Questions? Ask them here.

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Q: As somebody who wants to move away from full time work to more optionality, what options do you find yourself considering? How different is advising from consulting?

Last week someone asked me this question and I realized I had never written down all of the options that I’ve explored. I have written a bit about the phases of your career and what a Growth Advisor does (how I spend some of my advisory time currently). But never laid out what it means to pursue and unlock optionality in your career.

In this newsletter I’ll break down the different options I’ve pursued and my take on each one. I invite you to contribute your thoughts on this and your own explorations of optionality in the comments at the end.

Reforge Expert in Residence (EIR)

This is an option that isn’t available to everyone, but I need to start here because it’s an important part of the story. I started with Reforge as a backdrop to provide some stability in my solopreneur journey. Being an EIR at Reforge is a part-time, W2 job. I get a paycheck twice/month in exchange for running programs like the Growth Series, Advanced Growth Strategy, and Growth Leadership (which I also created; more on that later). 

Being an EIR at Reforge was really helpful for me at the beginning because I wasn’t sure about other paths of optionality and I needed some stability to explore. It has some similarities with other EIR programs, like at VC firms, in that it gives you that space to learn about other businesses with a backstop of monthly income. It’s also very different from other EIR programs—I construct, teach and facilitate Reforge programs which are very time intensive a few times per year. 

One bonus is that it has provided me with some important skill building that I overlooked at the beginning. I now know how to facilitate discussions amongst (virtual) rooms of 300-500+ people. And teaching has turned out to be one of the most enjoyable components of my career optionality phase.

Advising

Advisors will all have slightly different definitions of what they do. I’ve written a piece on what a Growth Advisor does that you should read if you’re curious. The non-standardization of advising can actually complicate finding engagements so it’s really important that you define what your particular approach to advising looks like.

For me advising is a cross between teaching, coaching, and organizational problem solving. I’m helping CEOs, founders, and other CxOs (and their teams) build practices that accelerate their growth, product development, or hone their strategies. It blends strategic and tactical advice with some coaching (depending on the engagement). Engagements tend to last between 6-12 months or sometimes longer. 

Much of what I help with are hands-on implementations of many of the concepts that I teach or have taught at Reforge or elsewhere. I’m able to work with ~5 companies at a time because I can leverage frameworks and artifacts I’ve successfully created and used elsewhere. I then layer on the uniqueness of the specific business like their use case(s), customer base and growth model. I’m helping companies see around corners, skip a ton of extra work, and make more optimal decisions. They get the benefit of 20 years of experience in a concentrated form.  

From a compensation standpoint, advising is really effective for me. It provides a high dollar value per person hour and helps companies make decisions way faster than they would otherwise. But advising is not without challenges. For starters, it’s a largely word-of-mouth driven business so each engagement is a chance to earn (or lose) a referral. I also have to practice all of my reverse interviewing skills ahead of each engagement to make sure I’m able to help them with their specific challenges. Sometimes, I miss something in this process and realize after I start that I’m not the right fit. Because the advising market is highly fractured and non-standard there’s an education component on what is (and is not) possible with each engagement. Oftentimes people are looking for hands-on consulting which is very different from advising.

This is a good time to take a brief tangent to answer the second question: 

How different is advising from consulting?

Very.

Advising is around 1-2 hours of meetings per week and about 2-3 hours of  asynchronous time per hour of live meeting time. Consulting is a lot more asynchronous time, very project and deliverable focused with specific artifacts that come out of it.

But you can do fractional consulting -- where you're working "part time" with a company and handling deliverables. The structure of the agreement and compensation will look very different from advising.

Consulting

Earlier in my career I did some consulting work after my time at Lyft. I was spending about a day a week in the office with a few different companies, running aspects of their business, and sometimes directly managing the work of team members. Now you’d call something like this “Fractional” work and structure your time accordingly (probably no more than two companies at a time depending on your bandwidth). 

For me, consulting isn’t the highest leverage use of my time. It’s much more time intensive than an advisory relationship and is less of a partnership and more of an employer / employee relationship. You have specific projects, deliverables, and timelines you need to adhere to, but you’re also operating at arms-length from a company so you can have a harder time accessing the resources you need to get the job done. On a pure dollars per hour basis it’s lower than advising and also doesn’t effectively utilize decades of skills to advance the thinking of CEOs, founders and other executives which is very high leverage.

The ideal structure for consulting is one where you are able to operate fully autonomously with access to all the resources and tools you need to get the job done. At that point, you’re probably better off operating as a fractional team member and committing a larger chunk of your time each week.

Interim Work

I define “interim” work as full-time with an end date. It is different from fractional work because here you’re spending the majority of your time in a given week with the company you’re working for. In my most recent interim role as the CPTO at ResortPass I was responsible for the entire product and technology organization: hiring, performance reviews, strategy, being part of the executive team, delivering the roadmap, etc. It was a full-time job like any other in-house executive role.

The difference was that I had a defined period of time that I would be there and the end goal was to hire my replacement (still looking btw!). The work was scoped with a set of very clear deliverables, and as an example here they are:

• Join as the interim Chief Product & Technology Officer at Resortpass with the existing product and engineering teams reporting to me.

• Coach and manage team members (regular 1x1s, etc.)

• Participate in required leadership meetings as defined by the CEO

• Prioritize and evolve roadmap; assist team in execution

• Recruit and hire additional roles for the Product team. (note: I spelled out these roles in the agreement)

• Support the hiring of replacement VP Product or CPO and other leadership roles as needed

• Deliver ~18-24 month Product Strategy and ongoing roadmap

• Deliver team topology (product org design)

• Assess and adjust (as necessary) product development processes

The advice I would give here is to make sure that the deliverables are really clearly defined (as above) and unless you want the time frame to be open ended (which isn’t really “interim” in nature) you have to define your end date. 

From a compensation standpoint the Interim role can be lucrative but it won’t be the highest dollar value per hour. My interim roles tend to include both cash and equity compensation and so I’m much more selective in the companies that I choose to work with as a result.

Coaching

I think almost everyone would benefit from having a coach, but being a coach is not for me. I wrote an entire newsletter on this where I interviewed two exceptional coaches, including one who was my coach for many years of my career. 

For me, coaching isn’t the ideal use of time. It can border on therapy, which isn’t something that I’m trained in (for good reason) and the emotional energy required of the coach can be a lot. Coaching is also very focused on an individual whereas advising is focused on the entire company. As someone who is very results-oriented I find that advising is a better fit for me because I can see the tangible impact of my work (numbers move, products get built, etc.). But for some people who want to help out on a one-to-one basis and help people transform their careers it’s a perfect fit for their personality and skills.

From a compensation perspective coaching tends to be less than consulting and advising on a per hour basis and the work just looks different. My advising practice does have an element of coaching to it, but that tends to be more about tactical coaching that benefits the company (ex: how do you build a growth model, what does a great product strategy look like, how do you rebuild onboarding) than it is about individual improvement.

Workshops

I’ve done a few of these and I’d describe them as “advisor-in-a-box.” If you can templatize them then they are a good addition to your optionality toolkit. A workshop combines education with practical application. It usually involves me teaching a concept (ex: growth model or use case mapping) and then fitting that concept to the company in a hands-on way. 

My challenge with workshops is the limited follow-up and implementation of the workshop. This is why I like to pair workshops with advisory relationships because then the relationship doesn’t start and end with the workshop. 

From a compensation standpoint these can be highly lucrative, but feel very transactional to me. As a solopreneur it’s the difference between a purchase and a subscription. One approach I’ve taken is to leverage the workshop as a kick-off to the advisory relationship. This has been very effective because we can spend an intensive 1-2 hours of time together working through a problem and then check in on implementation of that throughout an advising relationship.

Courses

I mentioned earlier that I would circle back to this so here it is. I built the Reforge Growth Leadership course with my pal Elena Verna. It was my first program at Reforge and I’m very excited about the feedback we’ve received. Creating a course is an incredible amount of up front work; we spent months on this program turning our experience into frameworks, templates, processes and tools with the amazing Judy Merzbach. 

If you’re creating a course not as part of Reforge one of the main things to know is that you need strong distribution. If you don’t have your own audience then you have to leverage someone else’s like one of the existing cohort platforms (ex: Maven). Even on Maven, the success of your course is often predicated on your ability to market it and drive adoption. 

Course creation is an LTV game. The upfront time investment probably won’t pay off in the first run of the course, but (hopefully) will over subsequent runs because the time required is significantly less after you create it. There’s also a tradeoff between what’s popular now and evergreen creation. You can sell a lot of AI courses now, but in a year or two maybe not.

One word of caution on course creation: like most platforms it follows a power law distribution. The really successful course creators you read about are the top 1% of the platform. Most courses make a small amount of money (or zero). So as with building a product make sure you’ve got some PMF before you go all in.  

Paid Speaking Engagements

I’ve done a handful of these—Amplitude’s Amplify and Cohort conferences, Adobe’s PLG speaker series, and Microsoft. I love speaking engagements and would gladly do more of them now that we’re returning to in-person events. Hit me up here if you’ve got one you’d like me to join.

These tend to be less lucrative on a per hour basis than other work, but can be helpful for testing out new frameworks and getting feedback. If you’re into personal brand building they can also be helpful with that and you get a bunch of media assets that you can use in the future.

Membership / Subscription / Advertising

This is an avenue that more of my peers are starting to pursue. Lenny Rachitsky is one of the most recent to demonstrate that you can build a really meaningful second career out of monetizing your newsletter and podcast. We’ve also seen a lot of transparency recently from folks like Elena and Leah Tharin about their newsletter monetization journeys. One of the best conversations on this topic is the Acquired podcast episode with Ben Thompson of Stratechery who is an early pioneer of this model and the reason that platforms like Substack exist.

I obviously think this is great (I worked at Patreon for 4+ years) and I will eventually monetize this newsletter and my podcast when the time feels right. Right now, however, this work is more of a labor of love than one of financial gain. One of the reasons to run and monetize a newsletter is that you can own the relationship with your audience independent of any other platforms and their algorithms (a lesson I also learned at Patreon before it was fashionable to talk about it). 

There are also more practical reasons to do it; like if you absolutely love writing. I write about topics I’m passionate and curious about and also that I know will help people. If you don’t love writing then it can be really hard to stay consistent with it because you’ll gravitate towards the work that you do love and sacrifice the cadence and quality of your writing. If you’re starting writing because you want to build a business I’d advise against it. Start with your passions and interests then add the business model.

Also, as with course creation there is a power law. While you only need 1,000 true fans to earn a living as a creator, many won’t get there and if you live in a high cost of living area (looking at you California) you’ll need more than 1,000 true fans to pay the mortgage.  

Investing

I do some of this and hope to do more over time. Right now, because I’m early in my lifecycle as an investor, this is actually a cost center rather than a revenue generator. But I’ve recently gotten involved as an investor with 20VC in a subsidiary investor group where I get to invest someone else’s money alongside my own. For me right now this is much preferable because the payback cycles are longer and uncertain. Also I have no aspirations of being a full-time investor; I like operating too much!

Conclusion

I’ve been doing marketing, growth or product management work for ~20 years at this point and only recently have gotten to a place where I’ve finally unlocked some optionality. I spent the 15+ years before getting here working on the first two phases of my career: validating impact and demonstrating repeatable success.

I think there’s a hunger and a sense of urgency amongst a lot of people who are earlier in their career that they want to accelerate to get to the optionality phase. I understand that. I’ve been that person and I don’t think it went very well. I didn’t have enough lived experience, frameworks, and repeatable success to share with people so I ended up doing a lot more work and pushing myself beyond capacity. I don’t recommend it.

However, when you’re ready to start exploring what unlocking optionality looks like I recommend trying some of what I’ve explained in this post. I’m also very curious to hear about how other people have unlocked optionality in their careers and what they’ve learned. Feel free to leave me a comment with your thoughts!