Strategy Meeting
Artifact info
Title:

Yoana Tchoukleva Website - Project Restart

Engagement:

Yoana Tchoukleva - Website

Client:

Yoana Tchoukleva

Meeting Date:
April 23, 2026
Next Meeting Date:
May 24, 2026
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May 24, 2026
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May 1, 2026
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People
James Redenbaugh
Yoana Tchoukleva
Artifact Image
Meeting Summary

Project Context & Reconnection

After a significant pause, Yoana and James reconnected to restart her personal website project (15:03). Yoana is currently on maternity leave through May 18th and wants to make focused progress while her mom is visiting and helping with the baby. Her full-time job provides her primary income, but she's building toward taking on side engagements in justice work and legal consulting, which makes having a simple professional web presence a priority.

Strategic Vision for the Site

Yoana articulated two clear intentions for the website (54:40):

  1. Professional presence - A place where people in the Bay Area (and increasingly online, worldwide) can learn who she is and what she offers for consulting, mediation, and legal gigs outside her day job.
  2. Personal archive - A central place to track publications, podcasts, and milestone accomplishments. As she put it, life moves fast, and she wants a space to reflect on what she's done and one day share it with her daughter (55:40).

The site should feel personal and impactful without being exhaustive - not everything about her life, just the meaningful highlights.

Review of Previous Progress

Much of the foundational work from the earlier engagement remains usable:

  • Logo designed collaboratively in Figma
  • Initial content draft in a shared Google Doc website outline
  • Figma board with layout ideas, photos, and sitemap (About, Offerings, Publications, Contact)
  • Domain securedioana.live (the deliberationcollective.net domain will be allowed to expire since a former colleague now runs a similar collective Yoana is part of)

Yoana noted that sifting through photos via Discord and browsing templates were the main time sinks previously, and she'd prefer to avoid those steps this round (32:28).

Platform Decision: Squarespace

After exploring options, the team landed on Squarespace as the right platform for this project (47:13). Key reasons:

  • Yoana's partner's site is on Squarespace, so learning it has dual value
  • DIY editing is straightforward - "what you see is what you get"
  • Custom features can still be layered in to make the site feel unique
AI-Managed Alternative Explored

James demonstrated an emerging approach where sites are hosted on GitHub [tag="github"] and managed conversationally through Claude [tag="claude"] - no manual CMS editing required (35:19). He showed a complex personal project (a global directory of artists, musicians, and activists) built largely through this workflow, plus a simpler client prototype where new pages, content edits, and images can be added just by dialoguing with Claude.

The tradeoff: Claude-managed sites require less manual work but add an AI intermediary between the user and the output. Squarespace offers more direct control. Yoana was intrigued by the Claude/GitHub approach as a future direction but wants to start with Squarespace to build hands-on familiarity (47:13).

Content Strategy

James emphasized that the next critical step is content (56:28). Yoana will revisit the Google Doc outline and update it with:

  • Overall intentions for each section
  • Specific copy where she has it
  • List of accomplishments, publications, and milestones to feature

The previous draft was likely too long - modern personal sites are shorter, and the offerings section in particular should grab attention rather than exhaustively explain her methodology (57:27). Yoana plans to use Perplexity to help refine tone and tighten copy.

James will also share precedent sites from past personal brand and consultant clients to help Yoana find reference points that resonate without becoming templates.

Design Direction

Yoana wants a muted background with vibrant pops of color, echoing the yellow, red, and green of her logo. She likes clean fonts and boxed layouts, and wants to avoid the dense, endlessly-scrolling homepage pattern she saw on some friends' sites. Roughly 10 photos should be sufficient - far fewer than originally planned.

Budget & Timeline

The original proposal was $2,000 total, with $1,000 already paid. The original scope included five creative sessions, style guide, logo, Squarespace setup, sitemap and content coaching, graphic assets, and site customizations. James estimates they're roughly halfway through.

Plan going forward:

  • Yoana sends the remaining $1,000
  • James resends the proposal as a PDF (original Bonsai link expired)
  • Launch target: end of May (before James leaves for a conference in Portugal followed by vacation)
  • If scope expands beyond the original proposal, additional work will be billed hourly

Yoana also flagged interest in eventually creating a brand kit and newsletter through Squarespace for social media consistency.

Action Items

Yoana Tchoukleva

  • Send the remaining $1,000 payment (01:07:36)
  • Update the Google Doc website outline with refined content, intentions, and accomplishments by Monday (01:08:35)
  • Review Squarespace templates and personal-brand inspiration sites; gather any additional visuals (59:43)
  • Text James Monday with a progress update and schedule the next working session (01:11:11)
  • Let deliberationcollective.net expire; proceed with ioana.live as the primary domain (51:34)

James Redenbaugh

  • Resend the project proposal as a PDF (01:10:49)
  • Share precedent examples of personal-brand and consulting websites (58:34)
  • Generate interactive Squarespace mockups from Yoana's updated content (33:02)
  • Support content refinement and narrative shaping once draft is in (56:28)
  • Drive toward end-of-May launch ahead of upcoming travel (01:08:02)
Relevant Initiatives

Personal Website - Design & Development

Priority: 
High
Size: 
M
Planning Stage
Transcript