Written by: Sabina Wiley
Published on June 30, 2026
Quest Log
Side Quest: Reinvent your entire career while solo parenting, finishing a degree, and pretending you have it together.
Difficulty: ★★★★★ + ∞
Status: Upright. Mostly.
Unexpected Loot: A career I’m actually building, an MBA I’m pursuing, and the humbling discovery that adulthood has absolutely no onboarding program.
Nobody put it in the fine print.
Not in the marriage certificate, not in the military spouse orientation packet nobody actually gives you, not in any of the parenting books I read with the misguided confidence of someone who thought preparation was the same thing as readiness. Nobody wrote down that adulthood — real adulthood, the kind with a deployed spouse and a toddler and a career pivot happening simultaneously — would feel less like a plan coming together and more like trying to assemble furniture without the instructions while someone small screams at you from the next room.
Which, for the record, is a particular kind of cruel joke when you are someone who has had a one-year, two-year, five-year, and ten-year plan since approximately the eighth grade.
I am not an athlete. I have never competed in anything that required a jersey or a starting line. But if overthinking and self-analysis were Olympic sports, I would be a decorated veteran. I have color-coded my future. I have built contingency plans for my contingency plans. I have sat with a blank calendar and felt genuine excitement about the organizational possibilities.
And then life went completely off-script, and I had to figure out what a planner does when the plan is no longer relevant.
Spoiler: it is not graceful. It is not graceful at all.
The pivot nobody briefed me on.
When I found out my husband was deploying to a combat zone — a region I was not allowed to research without immediately catastrophizing, which is its own special kind of torture for someone who processes anxiety through information-gathering — I was six months pregnant and running on the specific kind of tired that does not respond to sleep. I had a federal career I was proud of. Two agencies, complex work, the kind of professional identity you quietly rely on to remind yourself you are a person with skills and not just someone who has forgotten what a full night’s rest feels like.
None of this was in the ten-year plan. Zero percent of this was in the ten-year plan.
The two-hour one-way commute while solo parenting a newborn made the decision for me. I walked away from federal service, turned in my creds, and stood in a parking lot wondering what exactly I was supposed to do next — which, as a lifelong planner, is genuinely one of the more unsettling places I have ever stood.
What I did not anticipate was how disorienting it would feel to start over without a roadmap. Not because I was unprepared — I am constitutionally incapable of being unprepared, it is simply not available to me as an option — but because no amount of preparation actually cushions the specific clumsiness of beginning again mid-stride. You know things. You have skills. You have opinions about stakeholder management and operational efficiency. You are also, somehow, the newest person in the room, learning a new industry’s rhythms while simultaneously learning that toddlers have no concept of your deadline and even less sympathy for it.
The part that got me was not starting over. It was starting over without being able to benchmark my progress against the version of myself I had planned to be by now. That version had a different title. A different trajectory. A very organized five-year projection that is now laughably irrelevant, which I say with love and only moderate grief.
What nobody tells you about career pivots is that they are humbling in the most unglamorous way.
Today I work in project coordination supporting a team of forensic engineering consultants across complex technical cases. The work is genuinely interesting — the kind that requires you to think, adapt, and operate across moving parts with competing priorities. The skills I spent years building in federal service translate more than I expected. What did not translate was the assumption that starting somewhere new would feel graceful.
It does not. It feels like learning a new language while simultaneously teaching a toddler not to eat crayons. You are competent and confused at the same time, which is a deeply uncomfortable combination that nobody adequately prepares you for — and which is particularly destabilizing when you are the kind of person who has historically preferred to be competent and thoroughly briefed.
Parenthood has the same energy, for what it’s worth. Adequate planning does not prevent the permanent three-day lag. You can have the schedule and the color-coded calendar and the backup plan for the backup plan — and trust me, I have all three — and you will still find yourself standing in the kitchen at 7am in yesterday’s clothes, out of coffee, trying to remember which version of today’s plan is still operational.
I spent a genuinely embarrassing amount of time being frustrated with myself for not keeping up with the imaginary, better-organized version of me who was apparently handling all of this more efficiently somewhere in a parallel universe. The competitive streak that was supposed to push me forward kept turning inward, measuring me against a projection I had made before I knew what I was actually dealing with.
Rewarding? Absolutely. A scam? Also yes. Both things are true and I will not be taking questions.
What I did while I was finding my footing.
Somewhere in the middle of feeling perpetually behind a plan that no longer existed, I started doing something that made no logical sense: I started applying for things.
Not because I felt ready. I was definitively not ready. I started because I built a spreadsheet called the 1,000 Rejections Challenge — a running log of every application, pitch, scholarship, and slightly unrealistic idea I threw into the world — and somewhere in the act of tracking attempts, I found the only antidote that actually worked for me: turning the competition inward in a direction that was useful. Not measuring myself against the ten-year plan. Measuring myself against yesterday’s version of me, who applied for one fewer thing. (The full origin story lives here — read the 1,000 Rejections spreadsheet post.)
The spreadsheet did not fill with rejection the way I expected. It sent me across the country to accept a scholarship at a gala I almost declined because I was tired and it felt like too much. It earned me a writing competition win. It walked me through the Obama Presidential Center before it opened. It funded, piece by piece, an MBA at the University of Illinois Urbana-Champaign that I am finishing one late-night session at a time — after my daughter is asleep, because that is the only quiet window that exists, and I use it.
Between scholarships, grants, and being relentlessly specific about applying for every dollar available to military spouses and working professionals, I am on track to finish that MBA for under $10,000 out of pocket. I am writing that full breakdown soon — every scholarship, every application, every yes and no — because that is the post I wish had existed when I started. [Stay tuned — or subscribe so you don’t miss it.]
Here is what I know now that I did not know in that parking lot.
The ten-year plan is not coming back. I have made my peace with this, mostly, on good days, when the coffee is hot and my daughter is not shrieking.
Starting over is clumsy and slow and occasionally you will feel like everyone else received a briefing you missed. That feeling does not mean you are behind. It means you are in the middle — which is not a place a planner loves to be, but which turns out to be the most interesting place in the story if you can stop trying to skip ahead to the part where everything makes sense.
Adulthood did not come with fine print. Parenthood came with even less. Career pivots come with the vague instruction to “trust the process,” which is genuinely unhelpful advice that I resent every time someone offers it, particularly when I am the person who wanted to outline, annotate, and color-code the process before trusting it.
What actually helps is showing up anyway. Logging the attempts. Letting the spreadsheet be the plan when there is no other plan. Accepting that some days the most you can do is get everyone fed and remember where you put your laptop — and that counts. It all counts.
The footing you are looking for has been building under you the whole time. You just cannot see it while you are busy grieving the version of events you had already scheduled in your calendar.
Your Side Quest
Think about the last time life forced your hand and you had to pivot without a plan. What did you find out about yourself that you wouldn’t have learned otherwise?
A few questions worth sitting with:
- Where are you currently trying to find your footing — and are you being honest with yourself about how hard that actually is?
- What skill do you have that you haven’t given yourself credit for since changing directions?
- What would it look like to stop waiting to feel ready and just log the attempt anyway?
If you’re already mid–side quest, I want to hear about it. Drop it in the comments, find me on Instagram, or just let it sit with you for now. Either way — you’re not the only one figuring it out as you go.
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