Career Strategy Intensive plan · Wren Hollis (demonstration artist)

Premise

Ninety minutes, then this. It's built around one thing you said in the session: in sixty-two shows you've never once said it out loud. The clipboard has been on the merch table the whole time. It picks up whoever walks over on their own, which is about ten people a night out of forty-five, and nobody in that room has ever been told it's there. That answer reshaped most of what follows.

Everything in the first thirty days below exists to change that, because the audience is already there, about forty-five a night. Growing attention you don't keep is the most expensive way to run a project.

Decisions

Five forks came up. You called all five, and our lean sits next to each one so you can see where you overruled us.

01October or January

Release date: 9 October or January

Options: October keeps the momentum, and the residency falls the night before, so the room hears it live first. January gives time for long-lead press, which has already closed for October.
Your call: Keep October. Our lean was the same. The press you lose is press you weren't going to chase anyway.

02Single or EP

Format: single or third EP

Options: A single every ten weeks builds a cadence. An EP is a bigger moment and a longer gap.
Your call: Singles through 2027. Our lean was one more EP first; you were right that the day job makes EP-sized commitments risky.

03Tour or room

Touring: Texas and New Mexico, or the room

Options: Touring reaches new cities. The residency compounds where you already are.
Your call: Both, sequenced. Room first through winter, the tour opens 18 February 2027.

04Merch now

Merch: before or after the release

Options: Now means something to sell at the September residency. After means the artwork ties it together.
Your call: Now, one item. Our lean was to wait; you pointed out you have four nights before the release and nothing to sell at any of them.

05Self-managing

Management: self-managed or start looking

Options: Nothing about your current footprint makes a manager likely to say yes, and this plan is built for you to run.
Your call: Self-manage through 2027, revisit when the tour is booked.

Ninety days

Ninety-day plan

Dated, and split by who does what. Nothing here needs money you don't have.

When	Task	Who
Weeks 1 to 2	19 Aug to 1 Sep
	Add a mailing-list link to the Spotify and Instagram profilesTwo fields. Fifteen minutes.	You
	Rewrite the bio so it stops reading as traditional countryDraft in your folder; you approve the wording.	Both
	Order one merch item for the September nightShortlist and costings in the folder. Pick one.	Both
	Join the MLC and claim all eleven songsWalkthrough written against your accounts.	You
Weeks 3 to 6	2 Sep to 29 Sep
28 Aug	Master and artwork final, delivered to the distributor by 11 SeptemberBoth are hard dates. See the rollout calendar.	You
10 Sep	Say one sentence about the clipboard from the stage, September residencyThe clipboard is already on the table. What's missing is you telling the room it's there. This is the whole intervention.	You
11 Sep	Submit the Spotify editorial pitchOnce only, and only before release. There's no second attempt for this song.	You
	Shoot the September residency: three vertical clipsShot list in the folder. The quiet-room moment can't be recreated later.	You
	Batch all seven content pieces in one sittingPrompts written; you shoot, we cut.	Both
18 Sep	Announcement postArtwork, date, pre-save. Nothing before this is public.	You
25 Sep	Apply to the Prairie Line Songwriter GrantFirst of the two grants inside this plan. Answers drafted in the folder; you send it.	Both
	Register the six unregistered songs with BMISame walkthrough as the MLC step.	You
Weeks 7 to 8	30 Sep to 13 Oct
	Release week, day by dayThe checklist is in the rollout document. Follow it rather than improvising.	You
8 to 9 Oct	Residency Thursday, County Line out FridayPlay it live the night before it drops, and ask the room from the stage. Second time you'll have done it.	You
	Store live before release dayOne item, one page, linked from everywhere.	Us
Weeks 9 to 13	14 Oct to 17 Nov
to 23 Oct	Work the two-week post-release windowThe part almost everyone skips. Five dated actions in the rollout document.	You
30 Oct	Apply to the Small Rooms FundSecond of the two. Answers drafted in the folder; you send it.	Both
	Upload credits to all eleven songsYou confirm who did what, we do the uploads.	Both
	Write the second single, targeting a January releaseTen-week cadence starts here.	You
	Book the December and January residency nightsLock them before the venue's calendar fills.	You
17 Nov	Ninety-day reviewWhat worked, what did not, and the next ninety days.	Both

Eighteen months

Eighteen-month roadmap

Direction rather than tasks. This part is expected to change; the ninety days isn't.

Nov to Dec 2026: Cadence takes over from campaignsSecond single written and scheduled. The list is the primary channel by now, and every show adds to it.
Jan to Mar 2027: Three singles, ten weeks apartJanuary, March, and the third scheduled. This is the year the release rhythm stops depending on having enough songs for an EP.
Feb to Mar 2027: The Long Road Home TourEleven dates across Texas and New Mexico, opening 18 February, routed around the residency rather than replacing it. Routing locks late November 2026 and the announcement goes out 4 December.
May to Aug 2027: Collaboration, deliberatelyTwo co-writes with artists whose rooms you want to play. This is the fastest route to a new audience at your stage, and the credits fix in the ninety days is what makes it findable.
Sep to Dec 2027: Third EP, if the singles have earned itOnly if the list is past 2,000 and the tour rooms would take a return date. Otherwise keep releasing singles and don't force it.
Jan to Feb 2028: Reassess the self-managed questionWith a tour booked, a list of that size and a two-year cadence, the conversation with a manager is a different one from the one you'd have today.

Included

Deliverables included

Started, not blank. Each one is one working page, already filled in with your catalog and dates, so the plan above has somewhere to live from the first day. These are the starter versions; the full builds are separate services and the plan says where each one would earn its place.

Release timeline: County Line, dated backwards from 9 October, with the two hard deadlines marked.Full build: Rollout Blueprint
Royalty tracker: Eleven rows, one per song, registration state per registry, ready for the MLC step in week one.Full build: Revenue Review
Split sheet: Filled in for the two co-writes, ready to sign.Full build: Revenue Review
Goals tracker: The five decisions above, with the review date on each.Full build: Dashboard
Booking steps: The tour routing worked out to a target list of rooms, for February and March 2027.Full build: Booking Outreach
Weekly action list: The ninety days broken into a page you check on Mondays.Full build: Dashboard
Funding shortlist: Three Texas and national grants you're eligible for, with deadlines, listed below. Two fall inside this plan.Included, no full build needed

Funding shortlist

In a real plan these are real programs you can apply to, with their current deadlines. Here they're invented, because a real fund's deadline moves and a fictional artist can't apply to it.

Fund	For	Amount	Deadline	Fit
Prairie Line Songwriter Grant	Texas songwriters with a release in the last two years	$1,500	25 Sep 2026	Recording the second single
Small Rooms Fund	Austin artists with a regular listening-room night	$1,000	30 Oct 2026	The Tin Lantern residency
Northline Touring Fund	Independent artists booking a first regional tour	$2,500	15 Jan 2027	The Long Road Home Tour, once routing locks in late November

Session held 12 August 2026; plan issued 19 August 2026, within the five business days quoted. The ninety-day section is dated and expected to be followed. The eighteen-month section is direction and is expected to change as things do. Nothing here projects growth, income or a result, and the decisions recorded above are yours rather than ours.