Send It Anyway: Instant Access Replay

Thanks so much for joining Send It Anyway: Reframing Fear & Rejection in Creative Outreach. If you’re reading this after the workshop (or watching the replay), here’s a clear recap of what we covered — with core takeaways, plus the actionable steps + exercises you can use straight away.

Outreach can feel loaded — and showing up anyway is a big deal. You don’t need a perfect mindset, a perfect portfolio, or perfect words. You just need a repeatable approach and a little momentum.

Core Ideas That Landed

Certain moments during the workshop really resonated with those who came along:

  • “Detach self-worth from outcomes” (Tip #1)
    Many illustrators on the workshop resonated with this one — a strong sign it stuck.

  • “Rejection means you’re showing up” (Tip #2)
    Explicitly called out as a favourite.

  • Reframes like:
    “Rejection is re-direction”
    “Start with what you have”
    “You can improve later, by doing”

Takeaway: People didn’t want more tactics – they wanted permission to act imperfectly.

Outreach Realisations

A few honest, relatable moments in the session today:

  • “I’m realising how crappy my outreach emails are now”

  • “I’ve been introverted for years relying on people finding me… time to come out of my comfort zone!”

  • “I made a list of clients to contact… and then I just didn’t send”

There was relief in hearing:

  • January is hard for outreach (aka “the Monday of the year”)

  • Timing matters, but momentum matters more

  • You’re not behind!

Takeaway: Normalising hesitation reduced shame — and increased readiness.

Practical Takeaways Shared

From the community:

  • Use spreadsheets / Trello to track outreach

  • Colour-code lists to make them feel lighter

  • Gamify rejection (stickers, badges, shiny things)

  • Track sends, not responses

Takeaway: Making outreach playful + visible helps people keep going.

Community Energy

Strong, organic validation of the space:

  • Multiple members shared how supportive Inkygoodness Collective feels

  • Comparisons to other orgs highlighted the human-first community feel

  • Members actively reassured each other:
    “Don’t beat yourself up”
    “Our time is now”
    “You’re not alone”

Takeaway: The challenge feels safe because the community already is.

Momentum at the End

By the close of the workshop, the tone had clearly shifted:

  • “This is brilliant — just what I needed”

  • “Feeling much more motivated!”

  • “I feel ready even though I don’t feel ready”

  • Excitement for the 100 Rejections Challenge

Takeaway: Confidence didn’t arrive first — action did.

Watch the Workshop Replay now:

Core Tips & Takeaways

1) Your worth is not the outcome

Your value isn’t measured by:

  • instant replies

  • landing work immediately

  • praise or external validation

Your only job is to send the message. The outcome isn’t yours to control.

Exercise: Write down what you control vs what you don’t.


2) Rejection is proof you showed up

A “no,” a pass, or silence isn’t a verdict on your work. It means:

  • you took action

  • you practiced visibility

  • you entered the conversation

The goal is more sends, not fewer no’s.

Reframe: Sending is the win.


3) Reach out to “right now” people

Stop starting with the scariest dream clients. Begin with:

  • editors, studios, and brands already commissioning work like yours

  • realistic, aligned opportunities at your current level

Exercise: List 5 people you could email this week without spiralling.


4) Keep it human (not performative)

Good outreach is short, specific, kind, and clear. You’re not writing a cover letter — you’re starting a conversation.

Action: Find the person’s name. Avoid generic “Dear Sir/Madam”.


5) Tone matters more than pitch

Don’t beg, apologise, or over-explain. Strong outreach sounds:

  • calm

  • grounded

  • clear

  • respectful

You’re not asking for permission to exist — you’re offering something relevant.


6) Structure beats confidence

You don’t need the perfect words — you need a simple shape.

A strong outreach email has 4 parts:

  1. Why them (one genuine, specific reason)

  2. Who you are + what you do (one clear sentence)

  3. What you’re sharing (one relevant link/project)

  4. A low-pressure close (easy to respond to)

Action: Use one relevant hyperlink, not just your full website.


7) Say less than you think you should

You don’t need your life story, every credential, or a long justification. Keep it focused:

  • who you are

  • what you do

  • why you’re reaching out

  • one simple next step

Exercise: Draft your email, then cut it in half.


8) Make replying easy and low-pressure

End with a gentle doorway that respects their time. Examples:

  • “Would this be useful right now?”

  • “Let me know if this feels relevant.”

  • “Happy to share more if helpful.”

Low pressure increases replies — and keeps the relationship warm.


9) Consistency beats confidence

Don’t wait to feel ready. Build a rhythm:

  • 1 email doesn’t change much

  • 10 emails changes how you feel

  • 30 emails changes your relationship with outreach

Aim for small lists, simple messages, regular sending.


10) Momentum is built by sending

Confidence comes after action, not before it. You build a “sending habit” the same way you build any skill — through repetition.


What Art Directors notice (and what to respect)

  • Clear subject lines

  • Relevant work (tailored to them)

  • Respect for time

  • Persistence (without pestering)

Follow-up rhythm: every 4–6 weeks is a solid guideline.


Your simple action plan

Today

  • Choose 5 “right now” people

  • Draft 1 outreach email using the 4-part structure

  • Cut it down and make it human

  • Send it — or schedule it

This week

  • Send 5–10 messages total

  • Track sends, not replies

  • Note what felt easier each time

Scheduling tip shared

  • Avoid Monday/Friday if possible

  • Try mid-morning Tuesday (and match the recipient’s time zone)

Grab the workshop slides here.

Next step: 100 Rejections Challenge (starts 18th Feb)

If you want accountability and momentum, our 100 Rejections Challenge starts 18th February and runs for 90 days. It’s designed to:

  • normalise rejection

  • build resilience

  • detach self-worth from outcomes

  • create consistent outreach habits

The goal is 100 sends, not 100 yeses — and results often come as a side effect of showing up!

This challenge lives inside Inkygoodness Collective — a supportive studio-style membership community for illustrators and creatives building sustainable, confident practices.

By joining, you’ll gain access to:

  • the 100 Rejections Challenge

  • community check-ins and shared progress

  • masterclasses, portfolio crits and creative hub resources
  • live events & workshops and creative support year-round

More details about the challenge drop next week. We’d love to welcome you into the community and support you every step of the way!