Working It Out
Figuring out the future of a career in product
After watching comedian Mike Birbiglia’s latest show, The Old Man and the Pool I started listening to his podcast, Working it Out. Working it Out focuses on workshopping new material as a comedian. The material may be something Mike is working on or his guests. Ira Glass is one of his regular guests and I love Ira Glass. So I went back to listen to his episodes with Ira while he was still working on the material for The Old Man and the Pool. It was wild to listen to parts of the show in their early iterations knowing what the final results were. Ira would rip apart one of Mike’s monologues: highlighting what worked, what didn’t work, and asked probing questions about the value of a sentence based on the audience’s understanding of the story.
Greatness in any field requires immense dedication and humility. Even a seasoned comedian like Mike Birbiglia, with five successful comedy specials under his belt, invests countless hours refining his craft. His podcast and touring schedule showcase this ongoing commitment. This concept resonates deeply with me - striving for excellence while acknowledging your work is a work-in-progress. It's a delicate balance, and even more challenging in today's job market where vulnerability is discouraged.
For the past few months, I've embarked on a personal mission: building a business as a fractional product leader. Initially framed as an experiment, I was promoting myself as if this major career shift were already solidified. I was "faking it till I made it."
I haven’t made it; but I’ve learned a lot along the way. Devoting myself over the last few months has been a journey of invaluable self-discovery and validation of some false ideas I had about consulting. In the last few weeks some people reached out to ask what I’ve learned by trying it out so I wanted to share what I’ve learned by “working it out” in public like Mike Birbiglia.
If you’re curious about exploring fractional and are seeking a practical guide on how to do it, check out Aakash Gupta’s Substack; he collaborated with Jason Knight on this. It’s gold. As is Jason’s own writings on how to get into fractional.
But if you want to understand the emotional side of this experience, keep reading.
THE STATS
I started exploring fractional opportunities in earnest at the end of March, but have been doing research talking to other consultants since January 2024. From those conversations I started to craft a lightweight strategy that included: my unique value proposition, ideal client profile, and my tactics to secure up my first client.
I set a short-term goal of finding 1 client by the end of May giving myself two months to see if I could find traction. I had a few potential leads before I started in earnest, but essentially my pipeline was at zero. So I had to start somewhere.
Spurred on by my conversations and research, this is how I decided to position myself:
UVP: Building winning product teams delivering sustainable growth.
There were a few iterations on this UVP, but I decided to learn into the way I’ve pitched myself in the job market for a few years.ICP: Early Stage Companies (prior to the first Head of Product or VP of Product)
Sales Approach: Relationships. Lean on my network to help find ins. Failing this, sign up for fractional platforms that help talent find gigs.
This is how it went:
Total # of Conversations: 50+ meetings IRL & virtual
On average I was having seven networking conversations per week.Market Research Interviews: 6 fractionals and/or consultants; 4 coaches
Discussions with Principals & Operators at VCs: 5
Initial Outreach (Referrals): 47
These were emails asking for referrals to anyone may need someone like me or intro into VC community. I had 88% response rate; and the majority of my network replied in less than 24 hours.Fractional Platforms Signed Up For: 4
I focused on signing up for these for one week of my 8 weeks. So far it hasn’t net any leads.Unqualified Leads: 13
Qualified Leads: 4
Won: 1
This project wasn’t my ideal type of work, but it extended my runway by covering a couple months of administrative and marketing costs and a small pay cheque for myself.Lost: 3
WORKING IT OUT WITH OTHERS
Week by week as I was running through this process I went back to a quote I had written down back in March:
“If you’re overthinking, write. If you’re underthinking, read.”
I would alternate through periods where one was more true than the other. I started to feel stuck around week five. I was writing and I was reading but I needed to start having conversations with people about what I was feeling not just conversations where I was pitching my services.
So, I started to real talk. Over the past four months, I've relied on a small group of individuals to give me honest feedback. From their advice, I was forced to face that I was chasing something outside my wheelhouse driven by external validation and not my own fulfillment. I’m truly grateful: Kara, Anna-Roza, & Tyler. <3 Each of those three people listened, asked me questions, and shared their opinions while calling out their own biases. They were my Ira Glass.
My recommendation to people going through a career transition is to talk to as many people as possible but trust your best people. When you’re feeling low you need people who will puff up your ego but you really need the ones who will tell you the bald and honest truth. The kind of friends who communicate their opinion directly and have the facts to back it up. They pull out receipts of your own behaviour to show you that you’re talking the talk but not walking the walk.
This is not to say every single individual of the 50+ people I talked to in the last couple months weren’t impactful. Every conversation was a small step toward clarity. Thank you to everyone who picked up the (metaphorical) phone when I called. I am grateful; I know it is rare to have this kind of professional community.
WHAT I LEARNED
Fall in Love with the Business You’re Building
The best advice I received was from my ex-leadership coach (shout out Nancy John – she’s fabulous); she told me I needed to fall in love with building the business even more than the service I delivered.
I wasn’t in love with the business I was building; because I was positioning myself in a way that was aspirational and not really authentic. Imposter syndrome crept in because I was trying to fit myself as a square peg (product leader at digital transformation companies) into a round hole (pre-PMF early stage startups).
I truly believe you can learn to love the business building but you have to be deeply committed to the vision to ensure that love can grow.
Service ≠ Product
Consulting in whatever shape and form has similarities to building a product business but it is fundamentally different. You are the service, so relationships are everything. It’s like seeking venture capital money: investors believe in the founder more than the idea. I spent a lot of time focusing on honing the service and the value prop instead of refining the pitch of myself to get potential clients to believe in me. My stats are a result of that lack of polish.
My Network Was Not As Strong As I Thought
One thing I didn’t do before I started was take a really hard look at my network and the strength of the ties within it. My network is strong because when I ask for help, most people responded within 24 hours. That is outstanding; I’ve come to learn not many people can say the same. However, it was not strong in the sense that I had strong relationships with people who could hire me for a contract gig. I had to push through making second and third level connections to get to a proposal.
This isn’t an insurmountable obstacle. You can build the kind of network you need, but it is a massive undertaking. Prepare for it.
Quickly Build an Outreach, Networking, Sales & Marketing Machine
I put this off too often in my two-month journey. I felt like I was lost and wasn’t confident in my pitch so I held off on networking and outreach. At a certain point you need to be confident in your approach and just start putting yourself in front of people.
In hindsight, for me, I’m glad I put it off because I realized I wasn’t on the right path. Something was holding me back from really putting myself out there, and I’m glad I listened to that feeling. But if you don’t have that nagging feeling, accelerate on this aspect ASAP. Building this up is the most important step.
Listening to My Instincts
I hate to admit this, but it’s true. Three weeks into dedicating myself full-time to fractional, I knew I was on the wrong track. I remember one morning at breakfast I said to my husband: “I think I need to pivot” and I wrote it on a sticky note and I plopped it in my agenda for 2 weeks in the future. If any of you have worked with me, you know I have an uncanny ability to predict when things fall off the rails. So sure enough, when I saw that post-it two weeks later I knew I had been right. This is when the “stuck feeling” started to settle in.
Confidence, Imposter Syndrome, and Killing the Negative Chatter
This job market is brutal. It is fucking with everyone’s confidence. Shaking them to their core. The humans I’ve seen doubt themselves in the last 4-6 months are some of the most confident people I know. It’s a season, we’ll get through it. But the negative chatter will drag you down.
I let the negative chatter drag me down in the early days of this journey. Every day felt like crabs in the bucket. I allowed certain people’s feelings about the job market drive my decision making even if it wasn’t applicable to my own situation.
If you’re going down this path because of a layoff, avoid bitch sessions with your fellow laid off friends. Meet with them, but talk about any-fucking-thing else. Laugh about anything but the misery you’re feeling. You'll find more stability. I had to cut off contact with some professional peers because it was shaking me.
Avoid commiserating with laid-off colleagues. Focus on positive interactions, humour, and humanity.
Financial Health is a THING
I didn’t think I had enough runway originally to try this out. Turns out I’m hella risk averse because I had an eighteen month runway and I thought it was too little. I originally planned to go on this journey two years from now and with two years worth of financial runway. Everyone I talked to who was moving to consulting or had successfully transitioned to consulting for themselves had way less runway when they started. That also means there’s pressure for success; and that can drive an individual.
My situation is different. I have had a “Fuck Off Fund” since I was in my early twenties. I’ve used it many times and replenished it many times. This is one of those times where I’m using it. I make financial choices in my life to give myself the freedom of choice without fear. It feels like a shitty humble brag so I felt guilty talking about this with others. But when I let the financial pressure of others impact my thinking, I let fear creep in and started to dream smaller.
I need to dream bigger to figure out what is next for my career & life.
If financial health is a real constraint for you, talk to people who feel it as well. Lay out your options and map out different scenarios. Have a plan.
It’s Lonely AF
I knew loneliness was going to be a big hurdle going into this journey, especially because I was doing it alone. All ten solopreneurs I interviewed before trying this out said that they were lonely.
You need balls of steel to battle the loneliness of this journey. And a good therapist.
I highly recommend getting yourself a partner in an adjacent or complementary skillset instead of going it alone.
My Value Prop Wasn’t Sticking: People are OpEx
I am really good at building strong product teams. Good Strategy + Talented Peeps = Success.
This is a hard sell right now to companies with founders and leaders who are making very calculated decisions with their dollars. My friend Tyler gave me the best advice when I was walking him through a pitch deck I built. He said: “Where will the budget for this come from?” That advice forced me to put myself in my client’s shoes and whether I would spend this kind of money on the problem I was proposing to solve.
Product management 101, geez. 🙄
That chat with Tyler was my come-to-Jesus moment. When an executive/senior leader needs someone like me on the team, they’re probably going to hire someone full-time. There are some instances where that is not true – and I know people are doing fractional work successfully with this value prop because they’ve found companies with a need. But it’s a harder sell with a longer sales cycle.
In the same week as my conversation with Tyler I received two separate messages from product executives asking if I would be interested in a full-time role based on my positioning on my website and LinkedIn.
It clicked. 💡 When you need to help your people, you bring in a good people leader to make change in the long term.
WORKING IT OUT WITH MYSELF
For many of the reasons above and more, the last few months taught me that I started a new chapter but this has only been section one of that chapter.
Now I’m working it out with myself; figuring out what’s next.
That’s what writing this was all about (in ten drafts; thank you Gemini).
So what’s next?
On to the next experiment. From the personal side of things, I realized full-time fractional isn’t going to make me fulfilled or get me to some of my life goals. That being said, I’m going to keep experimenting and return to being open to full-time roles as well. That Open to Work profile frame is going up on LinkedIn.
In one of the 50+ conversations I had over the last four months; one fractional leader told me to “figure out how to productize yourself” because selling your time by the hour will only take you so far. This is one area I’m going to explore further by writing and building my thought leadership (ugh, I hate that phrase). While this post and this Substack are examples of thought leadership in product management; I’m doing it to help my favourite people — product people — while improving my writing. I don’t plan on monetizing it anytime soon, but I might try Substack’s pledge feature.
I will be writing about things that impact my own peer group: product leaders in the “sandwich generation” of management that is stuck in the middle between a rock (their team) & a hard place (their senior leadership/C-Suite). 😛 I want to combine some of the essence of my favourite newsletters in the world of product and leadership, like:
The World’s Best Newsletter for its advice on how to navigate the challenges of management while being a great leader.
The Beautiful Mess for its exploration on how to apply systems thinking to creating environments for product success.
Lenny’s Newsletter for its tactical advice that is applicable in the day-to-day.
If you don’t subscribe to the above three, I recommend you do.
So I’m excited to get back into writing and share some of my own experiences and advice.
I have a huge backlog of ideas from conversations I’ve had with numerous product leaders over the last six weeks. Many thanks to the product leaders I spoke with or those that I met at the Women in Product Conference and those I interviewed about your jobs, you’ve been my inspiration. While I like to think everything’s been written about, there’s still a lot to learn and improve in our craft. <3
Sign up below to get notified about the next post. I’m going to explain how I applied a product-market fit framework called the 4Ps to help re-position my services offering. I heard about the framework on Lenny’s Podcast with Todd Jackson from First Round Capital. It’s a great listen if you’re working on an early stage product.
My DMs are open if you want to connect further on testing out the fractional waters.
Subscribed! Very well written, thoughtful and to the point. While I've had a similar view that "everything’s been written about", there's always room for honest thought leadership (hah!) without promotional agendas.