Welcome on Own The Leap

What Day One Sounds Like Now

Wed, 10 Jun 2026 00:00:00 +0000

I did not intend to spend part of yesterday reading old posts.

Someone had left a comment on Day 3, and I went back to see what I had actually written, because I couldn’t remember exactly, and then I kept going. Day 2. Day 1. Then forward again from the beginning. I lost forty-five minutes and the dog was staring at me with the flat expression of a creature who had expected a walk twenty minutes ago and was prepared to wait indefinitely, but not quietly.

The One I Sent First

Tue, 09 Jun 2026 00:00:00 +0000

The dog and I did the loop at 6:15. Thirty-five minutes, same route. I did not rehearse anything, which was unfamiliar in a way I am still thinking about. For five days I walked that loop running the opener, the second paragraph, the one word I kept changing and changing back. Yesterday morning I hit send. This morning I just walked.

I checked my phone before I left the house. No response. Twenty-two hours in. I was not expecting one. I keep reminding myself of this. I am going to keep reminding myself.

The Third Monday

Mon, 08 Jun 2026 00:00:00 +0000

The dog and I did the loop at 6:15. I ran the opener the whole way, which I’ve been doing since Thursday, so I’ve been at this five days and I’ve stopped practicing and started pacing. I walked up the driveway and thought: you have now rehearsed this more than you have rehearsed anything in four years. You know the subject line. You know the word in the second paragraph you will change and then change back.

What I Thought This Was For

Sun, 07 Jun 2026 00:00:00 +0000

The dog and I do the same loop every morning. Thirty-five minutes, the same streets, the same three houses where the landscaping is competitive and the fourth house with the dead hydrangeas that have been there two years now and I keep expecting someone to deal with. The loop is useful. I do some of my clearest thinking between the second block and the turnaround.

This morning I was rehearsing the email again.

What the Subject Line Is

Sat, 06 Jun 2026 00:00:00 +0000

I sat down Saturday morning to write the email.

Not to send it. I am aware of the gap between those two things and I have been living in it for two weeks. But I thought: you can at least write a draft. You can open a compose window and see what it says. The calls are not calls you have to make from the office. Start there.

I opened a compose window and typed the name. One of the four non-contingent contacts, someone I have known for 12 years, a relationship I built on my own before I ever worked at this company. She runs operations at a mid-size software company, recently promoted to VP, the kind of role where you are suddenly responsible for renewals at a volume you have never managed before. I know exactly what problem she is having, or going to have. I have watched this problem develop in seven different organizations.

What Belongs to the Badge

Fri, 05 Jun 2026 00:00:00 +0000

I was on a call Tuesday. Another quarterly business review, the kind I have run enough times that I no longer need the agenda to know what I will say and when. Seven people on it, including a junior account manager who had done solid work. At the twenty-minute mark, she said something smart. An observation about the client’s procurement cycle that nobody had connected yet, accurate and specific, the kind of pattern that takes two or three years to learn to see.

Ready Is Not the Same as Going

Thu, 04 Jun 2026 00:00:00 +0000

The clearance arrived Tuesday.

Not permission. I know the difference and I keep saying so because I think I need to keep saying it. Legal clearance. The attorney’s opinion, not a guarantee, is that both contingent names fall outside what a court would likely interpret as solicitation under my agreement, provided I reach out after I have actually resigned. The missing exhibit cuts in my favor. I asked eight questions and got answers to seven. The ninth still does not have words.

The Email I Held for Thirty-One Hours

Wed, 03 Jun 2026 00:00:00 +0000

The attorney meeting lasted 43 minutes. I had planned for an hour.

She went through the non-solicitation clause quickly. I found that efficient, and then noticed I was reading efficiency as reassurance, which is not quite the same thing. The missing exhibit, the Restricted Clients list referenced in my agreement but not attached to my copy, turns out to work somewhat in my favor: a clause that points to a list it doesn’t include is harder to enforce than it reads on the page. She recommended I request the exhibit from HR anyway. I wrote that down.

I Didn't Know Anyone Was Reading

Tue, 02 Jun 2026 00:00:00 +0000

It is 7:42 in the morning and the attorney meeting is at 1pm. I have done everything I can do to prepare, which means I have approximately five hours of being ready with nowhere to put the readiness. The questions are numbered. The folder is on my desktop. The printed agreement has a Post-it on page three. There is nothing left to do that would help.

So I made coffee and sat down and found an email from a stranger.

What I'm Actually Asking the Attorney

Sun, 31 May 2026 00:00:00 +0000

I printed the employment agreement this morning. The copy I found in the guest room closet last week, eleven pages, originally printed on an HP inkjet I got rid of in 2021. It’s on my computer. I highlighted the clause on the PDF two weeks ago. I printed it again anyway.

Something about a legal document in your hand on a Sunday morning that is different from the same document on a screen. The screen version I’ve been reading for two weeks. The paper version I made coffee first.

Six Sentences After Four Years

Sat, 30 May 2026 00:00:00 +0000

The walk was forty minutes. I’ve done that route a hundred times: down to the park, around the pond, back up the hill. The dog ran ahead and waited. I was not thinking about the dog.

When I got home I opened the laptop before I sat down. I have learned not to give myself the option of sitting down first.

I typed her name in the To field. The woman who has been emailing me every December for four years asking whether I’ve thought about going independent. She left corporate six years ago, built her own practice, then went in-house at a portfolio company. She is a former colleague, not a client of my current employer. That distinction matters, and I’ll come back to it.

The Real Deadline

Fri, 29 May 2026 00:00:00 +0000

The scheduling email came at 8:47 this morning. I was on my second cup of coffee and my third work email of the day when I saw it, and I did the thing where I close the laptop and then open it again because I wasn’t sure I’d read it right.

The consultation is Tuesday at 1pm. Video call, forty-five minutes, bring your employment agreement.

I have known this was coming. I submitted the intake form six days ago. I knew a date would arrive and I would put it in my calendar. And yet when it came, I sat there with my coffee going cold and felt something I am still trying to name correctly. Not relief, exactly. More like: oh. So it’s real.

The Email I Keep Not Sending

Thu, 28 May 2026 00:00:00 +0000

I have a draft folder problem. Not a technical one. I don’t have things sitting in my email drafts right now, taking up space, waiting. What I have is a mental draft folder, and that is worse, because nobody can see it and I can pretend it does not exist.

I wrote six names down on Wednesday. The list is in my phone. Every name has a company and a note about how I know them and when we last spoke. I was careful about it, which is something I do when I’m nervous.

The Names I've Been Keeping in My Head

Wed, 27 May 2026 00:00:00 +0000

The attorney’s office acknowledged my intake form Tuesday afternoon. Two business days to schedule a consultation. It is Wednesday. I have been thinking about what I need to have ready.

The agreement, obviously. I’m going to scan it properly before I go in, not photograph it the way I photographed every school permission slip during the pandemic years, crooked, with my thumb in the corner. The clause is on page three. I’ll have it flagged. I am, it turns out, the person who shows up to legal consultations with a labeled document and a written list of questions. I suspected this about myself.

The Intake Form

Tue, 26 May 2026 00:00:00 +0000

The box is back in the closet. I put it away Sunday after I found what I was looking for, which is what I do with things I’ve dealt with and also things I haven’t. I’m aware those two states are not distinguishable from the outside.

I have the document. I know the clause. I know there’s a missing exhibit, something called “Restricted Clients,” that I either need to locate or find someone qualified to interpret without. I know exactly who can answer this: an employment attorney who represents employees. Not employers. The distinction matters and is not obvious from most law firm websites.

What Was in the Box

Sun, 24 May 2026 00:00:00 +0000

Sunday. Max got back from the lacrosse tournament around noon. He said it went fine in the way that means neither great nor terrible and moved directly to the refrigerator. Doug was mowing. Zoe would be asleep for another hour at minimum. I had approximately no excuse.

I went to the guest room closet.

The box was where I said it was, third shelf, under a bin of craft supplies I keep meaning to donate and a garment bag that has been in that closet since 2007 without being opened. I knew this because I had moved those items aside mentally at least a dozen times in the last week, which is a form of preparation I am apparently comfortable with but that does not actually retrieve the document.

The Agreement I Signed in 2002

Sat, 23 May 2026 00:00:00 +0000

Saturday morning. Doug was out getting the car washed. Zoe was asleep until a time I have stopped having opinions about. Max left at 7:15 for a lacrosse tournament I can track in only the broadest terms, and I found myself with a quiet house and no plausible excuse.

So I Googled it.

“Non-solicitation agreement standard terms.” Just typed it, hit enter, the way you finally pull a bandage you’ve been preparing to pull for two weeks.

The List I Won't Write Down

Fri, 22 May 2026 00:00:00 +0000

Thursday, second coffee, before a call that will definitely run long. I had seven minutes and I did what I’ve been doing with every scrap of found time lately: I tried to start the list.

Not a list I can put anywhere yet. I’ve done the health insurance research, or, not exactly done, I have two spreadsheet tabs and a saved bookmark for a healthcare.gov calculator I haven’t run all the way through. But I know the shape of it now: COBRA would be $1,840 a month for our family, which is enough to take seriously. The ACA marketplace option, depending on what I project for year-one income, might come out close to $1,100. Neither number is what I had in my head before I looked, which was something between “impossible” and “paralyzing” with no actual figure attached. The real figures are manageable. Annoying, but manageable. I did not expect to feel that way about them.

The Question I Hadn't Prepared For

Thu, 21 May 2026 00:00:00 +0000

The questions came Wednesday night, which was not when I expected them.

I had been anticipating a kitchen-table conversation. Serious. Probably after Zoe went upstairs. Doug would have a list, I would have answers, we would work through them the way two people who’ve been married for 21 years work through things: methodically, a little formally, with the television off.

Instead he asked the first one in the car. We were coming back from dropping Max at a friend’s house, 8:47pm, and he said, without preamble, “So what’s the actual timeline?”

Working Backwards from November

Wed, 20 May 2026 00:00:00 +0000

The questions still haven’t come.

I don’t know if Doug is being generous or strategic, but it’s Tuesday and he has not asked any of them. He made dinner last night. We talked about Max’s lacrosse tournament and whether Zoe’s college counselor is actually helpful or just expensive, and we watched forty minutes of television and went to bed. Normal in every direction.

I keep waiting for the conversation to resume and it keeps not resuming. This is starting to feel like its own kind of pressure. Like a held note.

The Part I Left Out

Tue, 19 May 2026 00:00:00 +0000

It’s Monday. Doug made coffee. I came downstairs, he handed me mine, asked how I slept, I said fine, which was true, and that was most of breakfast.

I was expecting more. The next installment of the conversation we’d started Sunday night, maybe. His questions arriving, one at a time, the way I’d been bracing for. What I got was a normal Monday morning, which I think was a kindness he was extending and I was too sleep-deprived to receive properly at 7am.

I Told Doug

Mon, 18 May 2026 00:00:00 +0000

Monday.

I told him Sunday night.

Not during a planned moment. I didn’t sit him down or open the spreadsheet or arrange the conversation the way I’d been rehearsing it. He was doing the dishes and I was at the kitchen table, and I started talking before I’d actually decided to.

Which is probably the only way I was ever going to do it.

Here is what I said, more or less: I want to leave my job. I have an idea for what to do instead. I’ve been building this whole thing in my head for months and not telling you, and I don’t know why it took me this long.

What I'm Actually Asking For

Sun, 17 May 2026 00:00:00 +0000

Sunday.

Yesterday I spent two hours building a competitive landscape and called it research. Then I wrote about how I’d called it research and it was actually avoidance. I felt very perceptive. Very honest with myself.

Then I woke up this morning and couldn’t stop thinking about what I would actually say to Doug.

Not whether to say it. I’ve settled that question. I know I’m going to say it, and I’ve known since at least Tuesday if I’m being honest, probably longer. The when is close enough now that I can almost feel it. But this morning, in that particular hour before the house wakes up, I was trying to put words to it and I kept running into the same problem.

The Productive Version of Hiding

Sat, 16 May 2026 00:00:00 +0000

Saturday morning. Doug went to get the car washed, which takes him about ninety minutes because he also stops at the hardware store and the place that does the good breakfast sandwiches. I know this because I have been married to this man for twenty-one years and he has never once just gotten the car washed.

I had ninety minutes. Maybe two hours if there was a line.

I should have done a lot of things with that time. Sorted through the pile of college brochures on Zoe’s desk. Called my mother. Waited for Doug to come home and said the thing I spent all of yesterday writing about needing to say.

What Strangers Know

Fri, 15 May 2026 00:00:00 +0000

Thursday. Day twenty-one. Three weeks.

I sat down this morning the way I’ve sat down every morning for three weeks, and that’s the thing I want to talk about. The sitting down has become automatic. I don’t bargain with myself about it anymore. I don’t wonder if I should skip a day. I get up, make coffee, open the laptop, and write.

Three weeks ago I wrote that I wasn’t sure I was “a blogger.” That I was using this as a commitment device. A public ledger for a private decision. If I wrote it where people could see it, I couldn’t quietly slink back to my desk and pretend nothing had changed.

The Line I Keep Scrolling Past

Thu, 14 May 2026 00:00:00 +0000

Wednesday. I opened the phone note this morning. The one titled “ideas” that I’ve had since early 2024. Nine items. I opened it on my second day of writing this and thought I’d sorted through it pretty thoroughly. One viable idea, eight dismissed. Case closed.

I was looking at item nine, the renewals consulting line. The 60-Day Save. The one I’ve spent three weeks building in public, the one Terri validated, the one I said out loud in my car yesterday to a windshield that had no feedback.

I Said It Out Loud

Wed, 13 May 2026 00:00:00 +0000

Tuesday morning. 7:43 AM. The highway, headed west. Coffee in the cupholder. Radio on, something about inflation I wasn’t listening to.

I said it.

“Your enterprise accounts are at risk and your dashboard doesn’t show it yet.”

Fourteen words. Alone in the car. The radio was still on, which meant I had to say it louder than I would have liked.

I’m not sure what I expected. A shift in air pressure, maybe. A physical confirmation that something had changed. That didn’t happen. It sounded like my voice saying a sentence I’ve been staring at on my phone for four days. No fanfare. Just highway and the tail end of a segment about grocery prices.

Case Study Number Four

Tue, 12 May 2026 00:00:00 +0000

Monday morning. Back at work. The problem statement from Saturday is sitting in my Notes app between a grocery list and Zoe’s SAT tutor schedule. “Your enterprise accounts are at risk and your dashboard doesn’t show it yet.” Fourteen words. I’ve been looking at them on and off all weekend the way you look at a parking spot you’re not sure is legal.

Today I watched it happen.

Quarterly business review for one of our top ten accounts. Twelve people on the Zoom. My manager leading. Slides about usage metrics, adoption rates, NPS trends. Everything green. The customer success team had that particular energy people get when they’re delivering good news they haven’t examined too carefully.

What I Typed Into Google at 7 AM

Sat, 09 May 2026 00:00:00 +0000

Saturday morning. Doug sleeping. Kids still asleep. Coffee made. Laptop open at the kitchen table because the bedroom desk felt too formal for what I was about to do.

I Googled “client retention consultant.”

I’ve been staring at three case studies for three days, and I know what I do, and I cannot figure out what to call it. So I did what every corporate person does when they don’t know something. I Googled it.

The Napkin at the Conference Dinner

Fri, 08 May 2026 00:00:00 +0000

Friday night. I told myself I’d write the third story and see if the pattern held. If it didn’t, I could stop pretending I’d found something. If it did, I’d have to figure out what to do with it.

It held.

Healthcare client, 2022. Regional health system, about fifteen hospitals, enterprise contract in year two of three. Classified as “green” in every tracking system we had. Usage steady, sponsors responsive, NPS in the high 70s. By every metric that mattered to my manager, a healthy account.

The Second Story Was Faster

Thu, 07 May 2026 00:00:00 +0000

Thursday night. Doug is downstairs. I know this because I can hear the specific silence of a man watching television with the volume at exactly 14 because he thinks anything above 15 is “blasting it.”

I opened the laptop at 9:40 and started writing the telecom story.

The $2.2 million renewal was Wednesday. Tonight I wrote the one from 2021. A telecom client, mid-size, three years into a five-year deal. Usage metrics looked fine. Better than fine, actually. Logins were up 12% quarter over quarter. If you were reading a dashboard, you’d say the account was healthy.

What If the Story Is the Pitch

Wed, 06 May 2026 00:00:00 +0000

Wednesday. I tried again. Not in the kitchen. At my desk in the bedroom, which is technically a desk but functions primarily as a place where mail goes to die. I moved three catalogs, a field trip packet for a trip that already happened, and a phone charger that doesn’t work but that I keep because it might. Optimism in a cable.

I didn’t open the one-pager. Instead I opened a new doc and started writing the $2.2 million story.

Why I Can't Write My Own One-Pager

Tue, 05 May 2026 00:00:00 +0000

Tuesday night. Doug is watching a documentary about bridges. Not a metaphor. Actual bridges. Infrastructure engineering. He watches these the way some people watch true crime. Zoe is in her room with headphones on. Max is allegedly doing homework.

I’m at the kitchen table with my laptop open to a blank Google Doc titled “60-Day Save: Service Overview.” I have been staring at it for twenty-two minutes.

I have written hundreds of one-pagers in my career. Literally hundreds. Service descriptions, capability summaries, client-facing proposals. I have reviewed them for my team. I have sent them back with comments like “tighten the value prop” and “lead with the outcome, not the process.” I know exactly what a good one looks like. I could write one in my sleep for someone else.

What I Think About in Meetings Now

Mon, 04 May 2026 00:00:00 +0000

Monday morning. 9:00 AM standup. Seven people on Zoom, four cameras on, three off. My manager is sharing his screen, walking through the Q2 pipeline review. I’m nodding. I’m making the right faces at the right times. I’ve been making the right faces in meetings for so long I could probably do it asleep.

Here’s what I’m actually thinking about: whether $12,000 per engagement is too high for a first client.

What My Mother Doesn't Ask

Sun, 03 May 2026 00:00:00 +0000

My mother calls every Sunday at 10:15. She has called every Sunday at 10:15 for as long as I’ve lived in this house, which is twelve years. Before that she called at 10:00, but I asked her once to push it back because Zoe’s swim lessons ended at 10 and I was always in the car when the phone rang. She adjusted without comment and has hit the new time with a consistency that I find both comforting and slightly unnerving.

Who Signs the Check

Sat, 02 May 2026 00:00:00 +0000

Saturday morning. Doug took Max to a tournament, Zoe is still asleep. I have the kitchen table, my laptop, and the question Terri asked me two days ago that I still can’t answer.

Who signs the check?

I have LinkedIn open. I’m looking at VP of Customer Success profiles at mid-size SaaS companies, trying to figure out who would pick up the phone if I called and said “you’re about to lose three of your biggest accounts and I can tell you exactly why.”

Forty-Seven Minutes

Fri, 01 May 2026 00:00:00 +0000

The call was supposed to be twenty minutes.

I sat down at 1:51 with my laptop open, my three questions written on a Post-it stuck to the bottom of my monitor, and a glass of water I’d already finished. Doug was downstairs. The door was closed. I’d told him I had a call with a former colleague, which is technically true the way “I’m fine” is technically true.

Terri called at 2:01. One minute late, which she apologized for, which made me like her again immediately. People who apologize for one minute are people who respect your time, and I have spent 24 years in meetings that start eleven minutes late with no acknowledgment.

What Do You Say When Someone Says Yes

Thu, 30 Apr 2026 00:00:00 +0000

Terri responded at 6:22 this morning.

I know the exact time because I was already awake, staring at the ceiling, running through the hierarchy of possible responses. The best case: enthusiastic yes, let’s get coffee. The worst case: polite deflection. The truly worst case: no response at all, which is its own kind of answer. I had prepared myself for all three. I had not prepared myself for what she actually said.

Asking for Help Before You're Ready

Wed, 29 Apr 2026 00:00:00 +0000

I woke up this morning and checked Terri’s contact before I checked the time.

6:14 AM. The text field was still empty from last night. My thumb was hovering again. I put the phone facedown on the nightstand and went to make coffee.

Here’s what I’ve learned about myself this week: I can diagnose a $200K account save in fifteen minutes, but I cannot write a two-sentence text message to a woman I used to eat lunch with every Tuesday.

Six Hundred Contacts and No One to Call

Tue, 28 Apr 2026 00:00:00 +0000

I spent twenty minutes tonight scrolling through my LinkedIn connections. All 614 of them.

I was looking for one person. Just one I could call and say: I have an idea for a consulting service, here’s the pricing, here’s the target client, is this real or am I flattering myself. That’s the bar. One person who could answer that question honestly and who I trust not to mention it to anyone in my current company by Friday.

Pricing Something You've Been Giving Away

Mon, 27 Apr 2026 00:00:00 +0000

I opened the yellow tab tonight.

Not on purpose. I was in the spreadsheet updating our grocery budget because Doug noticed we spent $87 at Whole Foods on what I described as “a few things for the week” and what the receipt described as twelve items including a $14 jar of olives. He didn’t say anything. He just held up the receipt the way a lawyer presents evidence, and I said “fair,” and then I was in the spreadsheet, and then I was in the other tab.

What I Said When He Asked

Sun, 26 Apr 2026 00:00:00 +0000

Doug asked me what I was working on last night.

We were on the couch. He was watching something about World War II, which is his version of meditation. I had my laptop open to a Google Doc that was very clearly not email. He glanced over, not suspicious, just making conversation the way you do when you’ve been married for 21 years and the other person is typing and you want them to know you noticed them.

I Already Did the Math

Sat, 25 Apr 2026 00:00:00 +0000

I went back to the spreadsheet last night.

Not because of the phone note. That’s what I told myself while opening it, the way you tell yourself you’re just going to look at the menu, not order anything. But I know why I opened it. Yesterday I found the one idea on that list that didn’t make me cringe, and the next thing my brain does, apparently without my permission, is start running numbers.

What Nine Ideas Look Like in Daylight

Fri, 24 Apr 2026 00:00:00 +0000

I opened the note.

The one on my phone. The one I mentioned yesterday, the one with nine business ideas I typed over the course of about eight months, mostly late at night, mostly with one thumb, mostly while I should have been doing something else.

I’ve been carrying it around the way you carry around a voicemail you haven’t listened to. You know it’s there. You know you should deal with it. But as long as you haven’t opened it, everything on it is still possible. Schrödinger’s career pivot. The moment I actually read the list, some of those ideas would stop being maybe and start being no. I wasn’t ready for that.

Why I'm Finally Starting This

Thu, 23 Apr 2026 00:00:00 +0000

The tab has been open in my brain for about a year and a half.

Not an actual browser tab. A mental tab. The kind that takes up space without loading. I would catch myself thinking about it on commutes, while making dinner, while half-listening to a status call I did not need to be on. I should write something. I should start something. I should figure out what comes next.

About

Mon, 01 Jan 0001 00:00:00 +0000

This is the story of one person deciding to stop waiting and take the leap.

Own The Leap is a real-time journal – not a retrospective from someone who figured it all out, but dispatches from inside the transition. The good days and the bad ones. The math that almost works and the fears that keep showing up at 3am.

If you are sitting in a meeting right now, hating your life, wondering if this is all there is – this is for you.

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Start Here

Mon, 01 Jan 0001 00:00:00 +0000

This blog is a real-time journal.

The person writing it is 49. She has spent most of her adult life in corporate jobs she was good at but never chose. She is trying to figure out what comes next before she turns 50.

She does not have it figured out. That is the whole point.

Day 1 — Why I’m Finally Starting This is where the story begins.

Posts go up whenever something is worth saying. There is no schedule. There is no niche. There is just what is actually happening.