Build-a-Business: Fractional CPO and Beyond
Real talk on what it has taken to build my business so far.
We all know the harsh truth: There is zero job security in tech anymore.1
Here’s what the past four years have looked like for me personally. How’s it been for you?
Finding meaning in the madness
In 2020, I was unemployed for first time since I was 14, during the worst pandemic of generations. There were very few jobs; I applied to all of them. LinkedIn was a ghost town. Help in the search was hard to find; forget “networking.” Everyone was holed up, hoping their cough wasn’t a death sentence. My job search took six months.
Fast forward two years. December 2022. The most wonderful time of the year? Nope! I was laid off with 20% of the company. This happened a few days after I had received a new job offer only to have it rescinded. And two weeks before Christmas. But there were more jobs this time. I applied to a few. LinkedIn was more helpful. Finding a job took six weeks from the time I was laid off. This was mostly because, since 2020, I had followed my own Always. Be. Interviewing. advice.
A year later, I found myself job searching, yet again. Telling my kids, yet again, that “Christmas will be small this year.”
(I know my story is typical for tech workers in these pandemic and post-pandemic years. My heart goes out to anyone reading who has been laid off or otherwise unemployed one or more times since 2020.)
Thankfully, this time the job market was more active and the job offers were easier to come by. But I had found Never Search Alone, joined a Job Search Council and was determined not to act out of desperation or land in a rebound job I would end up hating.
It was time to be intentional. Because being unemployed three out of the past four years had to mean something. I had to make all this madness mean something.
I decided to enter the world of build-a-business.
I felt done chasing certainty.
I decided to embrace non-permanence.
I (sigh) chose the road less traveled.
Side note: “The Road Not Taken” is often reduced down to a pithy “take the less familiar path” platitude. But if you read the poem, the traveler is describing both paths as equally untouched that day. He sumizes that it probably doesn’t matter which he chooses, but that he knows he will likely not return to also try the first one. It’s more about points of no return and regrets in our lives (hence the “telling this with a sigh”).
Your build-a-business questions
I’ve been asked the same four or five questions about my consulting business dozens of times in the past few months. So I thought I’d capture the answers to these questions:
How do you find customers (make money)?
What is “fractional”?
How do you do it all?
Can you teach me how to do it all, too?
Would you ever consider a permanent, full-time role again?
Question 1: How do you find customers (make money)?
Let’s face it: We’re all too comfy relying on our every-two-weeks bailout (paycheck).
So the scariest question for anyone building a business is, “How do you find customers (make money)?”
Well, I don’t have the magic answer but I would start by saying, “It looks and feels a lot like selling yourself while job-seeking.” And since, out of necessity, I’ve become an expert in job-seeking over the past four years, I’m now leveraging that to build my business. I figured …
If I’m going to be in constant hustle mode trying to find—and keep—a permanent role where I can make the people at the top (the ones responsible for all these layoffs) millions and millions of dollars, why not just do that for myself? I can constantly hustle and find clients across multiple streams of income instead.
There are currently five parts to how I make money:
Fractional Chief Product Officer for B2B SaaS startups
Product advisor to tech startup founders and CEOs
Career coaching for product managers and job-seekers
Brand-building (e.g., content creation)
Business and personal development
I haven’t yet monetized #4 so in some ways 4 and 5 are the same under the umbrella of business development/sales & marketing. They are both about building my top of funnel and eventually converting people to one of the top three options. So far, #1 is performing well. And I enjoy #2 and #3 immensely.
But I’ve only been at this a few months so I’ll let you know how each of the five are performing later this year!
Question 2: What is “fractional”?
According to Fractionals United, “a fractional executive is a highly experienced leader who works with a company on a part-time basis to provide leadership and strategic guidance.”
Fractional might be a good fit for “any SMB (small to mid-size business), startup, or scaleup that is on a budget but needs leadership expertise and experience to help them survive or thrive.”
To learn more, read this article.
Or watch this video.
I do fractional Chief Product Officer work, consulting and advising, depending on the needs of a business.
Question 3: How do you do it all?
The short answer to “How do you do it all?” is: I don’t.
The long answer is:
My life is really simple right now; I make sacrifices you don’t see.
There is a cost to my success you don’t see.
There is constant planning you don’t see.
I have help you don’t see.
The sacrifices you don’t see
I’ve broken down the average number of hours I spend “doing it all” below.
A few observations based on this data:
I spend almost as much time sleeping as I do working my main job of fractional CPO. I get an average of 7 hours of sleep a night. The rest happens as “catch up naps” on the weekend. This is the biggest sacrifice. My weekends are helluh boring right now, y’all.
Brand-building is taking a few different forms right now: LinkedIn content posts and commenting (never as much as I want to but I try for 3-5x a week), this newsletter (also something I wish I could publish more often, like weekly), speaking engagements on podcasts and LinkedIn Lives, potentially my own podcast (I’ve started banking a few episodes pre-launch).
Business and professional development often overlap. For example, I attended the Culture Builder’s Summit recently here in Utah for both purposes. Any time I agree to meet with someone new to do a coffee chat or connect informally (unpaid), I’m viewing it as biz dev for a potential client in the future.
Family time I defined here as only when I’m 100% focused on being in the moment with my husband or kids or occasionally extended family and close friends. My boys are older so we are nearing that “empty nesters” phase. There’s a lot of overlap with things like working on my laptop while watching a TV show with my college-age son, who is also on a device. I categorize that as work time, even though we enjoy hanging out and pausing the show often to heckle and laugh at random stuff. And of course, with older children, these are important moments that often end in really deep conversations once the screens are turned off.
My volunteer work is mostly focused on Product Hive at the moment, which I love and want to spend more time on in the future. (Check us out if you haven’t!)
Being human probably should take me more than 10-14 hours in a week but that’s all the time I have right now. Most of my lunches aren’t about being human; they are about my core work or business development, following the “never eat alone” principle. And I multi-task with work as much as possible while I’m doing things like walking on the treadmill or putting my face on in the morning.
The cost of success you don’t see
My consulting business is successful at the moment, for which I’m grateful. But it means I sleep a lot, stress a lot, worry & hustle a lot.
Sleep. I have to prioritize my “non-working” time on sleeping and spending time with my immediate family, in that order. I spend most of my weekends in recovery: marathon napping sessions (3-6 hours at a time), lots of binged TV while sitting on the couch, multi-tasking, and some connecting with friends and family. I don’t have time for hobbies, I have minimal time for self-care, I am constantly context-switching so I’m rarely present in the moment, and I am running at an unsustainable pace (my choice).
Stress. The stress is a bit like being back in college with the never-ending “The paper is due today!” feeling. You can’t exhale. There’s always something else to do, always something you’re currently or about to be behind on. And someone is always unhappy (but, hey, that’s just being a Product Manager!).
Worry & Hustle. On top of all that, you’re always worrying about where your next paycheck is coming from. You can never take a break from hustling for your next gig. Also, you can never take a break. Even though I’m on monthly retainers, I don’t have one-week or two-week long paid vacations built in. Something I plan to change going into my next gigs.
So before you see my life from the outside and start thinking about the next question (“Can you teach me how to do that, too?”), think again. You probably don’t want this particular version of my life. Keepin’ it real here, folks.
I have a few more months at this level of intensity and then, time for a complete reset and a vacation!
The constant planning you don’t see
The other secret to “How do you do it all?” is I am meticulous about my calendar. I have five tips for planning with purpose:
Assign every minute a job to do
Say “No” to To Do lists
Follow the 4 Ds: Do, Delegate, Defer, Drop
Plan weekly and daily
Update planned v. actual
1. Assign every minute a job to do
Every minute I’m awake is documented in my calendar. Every minute has a purpose. Even if (especially if) it’s 15 minutes of “Drive to the next appointment.” At the end of a week, every square inch of my calendar is filled with appointment blocks.
2. Say “No” to To Do lists
I am allergic to To Do lists. I never make them. Because every line on a list represents time spent doing that thing. So everything, and I mean everything, goes in my calendar. If I commit to do something, I’m committing time to do it, whether that’s 5 minutes or 5 hours.
3. Follow the 4 Ds: Do, Delegate, Defer/Delay, Drop/Delete
When I’m calendaring, I ask myself:
What can only I Do? Am I focused on the most important things?
From what’s leftover, what can I Delegate?
What can be Deferred (Delayed)?
What can be Dropped (Deleted)?
I have a rule that if I’ve rescheduled something more than twice, I drop it.
If it’s a personal task, it’s obviously not important enough for me to want to spend time on it right now. Delete. If it’s important enough, it will come back up again. (Or I need to consider delegating.)
If it’s something social like lunch with a colleague or a friend and they’ve rescheduled on me more than twice, I’m obviously not important enough for them to spend time with right now. Delete.
4. Plan weekly and daily.
I plan weekly on Sunday evenings and daily in the morning and at night. Sunday evenings take about an hour. For morning and night planning, I’m usually in bed on my phone so it’s quick—just a few minutes.
Weekly (Sunday night). On my laptop, I sync all my calendars onto my master calendar, schedule all the “big rocks” for the week work-wise and then I de-conflict from there. I have to be sure to add in all the “being human” stuff (e.g., workout, shower and get ready, eat, transition time, rest/break time). I have time blindness2—the inability to sense how much time has passed and estimate the time needed to get something done—so I have to pause and really think through things like:
“Is this enough transition time? No, really, is it? Let’s consult Maps and then add 10 minutes. No, add 15 minutes.”
“Is it realistic that this will only take 30 minutes? Let’s add some buffer.”
“Can I preempt any meeting overruns and block them out now so I’m not caught off-guard?”
“Have I scheduled time or help to procure the food and eat the food for every meal?”
As of Sunday night, everything for my week feels doable, organized, prioritized, amazing. But then, Monday morning hits …
Daily (morning). Inevitably, someone asks to reschedule something. This has a cascading effect. And keeps happening throughout the week. So on a daily basis, I’m doing calendar Tetris again.
Daily (evening). I update my calendar based on what actually happened that day. I attempt to do this throughout the day in near real-time but evenings are the final check. I also quickly look at the next day and see if there are any minor adjustments needed.
One of the things I’m subconsciously doing while planning morning and night for a few minutes is visualizing myself moving through my day. This helps with the time blindness and it helps me memorize my schedule. I have had this backfire on me if I memorize it wrong! I still look at my calendar throughout the day, but it’s helpful to have the mental notes.
5. Update planned v. actual
As I mentioned above, I spend time every evening updating all my planned time blocks and invites to what actually happened. Why? Three reasons: Reflection, memories, and memory support.
Reflection. Reviewing my day and updating the blocks of time or invites before bed is a good time for me to reflect on what I planned v. what happened and why. How can I improve going forward? For example, if I intended to make progress on a house project but spent time doom-scrolling through LinkedIn instead, I know I need to 1) stop it and 2) be more strategic about how to set myself up for success on that house project in the future. For example, perhaps I was too ambitious thinking I would want to do it on a Tuesday evening instead of on a Sunday morning when I’m freshest. I try to apply these learnings in the future.
Memories. Calendaring has become like journaling for me. I like being able to look back on previous weeks or months so I can enjoy the memories of that day, paired with any photos or videos I took.
Memory support. Detailed calendaring helps me beyond just being organized and (sometimes) showing up on time. It allows me to feel control over my time and my life in a way my brain doesn’t anymore. My memory has suffered so much from all the TBIs (Traumatic Brain Injuries) over the years. So it makes me crazy to look back at a day with an hour or more unaccounted for. An hour or more that’s just blank white space. How did I spend that time? Did I use it wisely? Did I waste it? What could I have done differently? I’ll never know because I don’t remember now and I won’t have record of it for the future.
My husband does not agree at all that I now have a bad memory, by the way. My short- and long-term memory has always been something of a superpower of mine. So he tells me that my post-TBIs memory is still better than 80% of people. I think he must really love me … and making up statistics.
The help you don’t see
I have a lot of help. Below are some examples.
Keep in mind these ebb and flow. I don’t have all of them active all at the same time. And I make sacrifices in other areas you don’t see to have this help.
My hope in sharing this list is that it provides you with ideas on areas it may make more financial sense to bring someone in to help than to do it yourself.
First and foremost is my amazing family. They do all the laundry, cooking, cleaning, dishes, everything. And they are constantly asking me, “What do you need? How can I help?”
We also have two dogs, one of whom sheds his entire top coat daily. So we have a housekeeper come in twice a week. It’s the only reason that particular goofball is still living with us.
I hired an Executive Admin who is going to take over my work and personal calendars. The scheduling has become more than I can handle. So I’ve brought in an expert.
I am a big believer in coaching. I have multiple coaches of my own. Executive coaching, content strategy / marketing coaching, business coaching, physical training/nutrition coaching.
I am a big believer in all the “woo.” I do energy work with my person regularly: reiki, foot zoning, Celtic shaman, readings. (She does remote sessions too!)
For physical and mental health, I rely heavily on my nurse practitioner, neurologist, detox/wellness clinic, and chiropractor.
I’ve struggled making “what to wear” decisions since I was in kindergarten. And I hate clothes shopping. My secret time-saver? Rent the Runway.
I don’t have time or patience to get my nails done at a salon. I have someone come to my house now. I also don’t have time or patience to do my own hair. I go to Pro Do blow dry bar 1-2x a week so I can work on my laptop while someone else deals with it!
Finally, I leverage generative AI constantly. Otter.ai for note-taking and to help remember everything. ChatGPT or Gemini to help with everything else. I never start working from a blank sheet of paper now, ever. (The one exception is when I’m writing this newsletter. I start from a blank sheet of paper and I never use AI except to grammar check passages.)
Question 4: Can you teach me how to do it all too?
If the above still has you interested in learning more about starting your own consulting work, I’d be happy to coach you and share more about what I’ve learned so far. You can schedule time here.
I would also recommend:
Join Fractionals United (FrUN)
Check out the LinkedIn content of FrUN and John Arms
Talk to others who are doing fractional
Don’t get caught up in “I need a logo first” or “I need a website first.” Get an LLC set up through LegalZoom, add a Calendly link on your LinkedIn for easy scheduling and get going!
Try pitching the “try before you buy” option to someone you’re currently interviewing with. You never know — they may love the idea!
Question 5: Would you ever consider a full-time role again?
Yes, I’m open to considering full-time Chief Product Officer roles. My Candidate-Market Fit statement is inclusive of full-time or fractional work. I’ve been actively interviewing for Chief Product Officer roles and there are some really exciting tech startups out there!
My Candidate-Market Fit statement: “I’m looking for a Product executive role in a B2B SaaS tech startup, 0-1 up to $200M, full-time or fractional.”
I hope sharing these answers to the most frequent build-a-business questions is helpful! We covered:
How do you find customers (make money)?
What is “fractional”?
How do you do it all?
Can you teach me how to do it all, too?
Would you ever consider a permanent, full-time role again?
If you have more questions, I’d be happy to answer them. You can schedule time here, drop me a note in the Comments below, or DM me on LinkedIn!
https://www.fastcompany.com/91054351/ai-job-security-2024-survey
https://add.org/adhd-time-blindness/