Real stories… that taught me hard truths… that compounded into promotions.

Hey Fellow Accelerators,

No long playbook this week. Instead, just some hard lessons learned from the trenches. Throughout the previous 12 articles I’ve always tried to ground the takeaways in real situations from my personal startup journey. So this week I’m bringing together some of the most formative ones. Here are 3 short stories from my early startup years. The completely unexpected shocks that forced me to grow, the last-ditch moves that worked, and the habits I kept. If you’re feeling the chaos right now, hopefully you can relate to one of these.

“Team of One”

On my very first day at my very first startup job (which also happened to be my very first job), I turned up bright-eyed and eager to learn from, grow with, and befriend my development team. Only I learned I was the dev team. No onboarding. No growth plan. But all the same expectation of results. My only support? Stack Overflow (IYKYK). While this was utterly terrifying, it also meant immense freedom; the same lack of direction that meant I had no one to learn from also meant there was no one who really understood what, or more importantly how much, I was doing. So I could coast… complain… or build my own development engine.

What I learned

More often than not, a development plan won’t be handed to you. But you can design your own.

👉 Action tip

Ask these three questions in your onboarding:

• “What does good look like in 6 weeks?”

• “What’s worked before I can mirror?”

• “How will we evaluate my work?”

Then send a one-line recap to confirm (“Good = X by Y, eval via Z.”). That’s your guardrail.

“The 10-Day Sprint With No Team”

At my second startup, I joined on day one convinced this onboarding could only be better than my first job. And even if it wasn’t, I’d done it all before... so surely I’d be able to handle it, right? Not exactly. Because while this time I was joining a team, it just so happened that every member of that team was on annual leave for the first five days of my onboarding. Oh, and I was handed a big new project with an 11-day deadline.

So… to recap: brand-new role, brand-new team, brand-new project, 11-day deadline and the first five days of it solo. I allowed myself a reasonable amount of time to feign working while quietly having a meltdown, but I knew I was running out of time to set myself up for the next two weeks. So, I mapped out a mini plan of action as best I could, asked for three resources (past examples that would point me in the right direction), and reviewed them so I had a bunch of follow-up questions to fire off to my manager before he got back from lunch on day 1. It wasn’t glamorous, but it was deliberate.

What I learned

Momentum beats perfection. Show your thinking, test small, move the work forward.

👉 Action tip

Whenever you feel like your projects are getting on top of you, send a five-line update to your manager covering the following:

• Goal → What’s the one outcome you’re driving?

• Progress → What have you shipped and what have you learned?

• Next → What’s the next step and when will you complete it?

• Risk → What’s the biggest risk/blocker and what’s your plan to solve it?

• Ask → What decision/resource do you need to keep moving?

This process grounds you. It reminds you how far you’ve already come, gets you thinking clearly about next steps, and opens up the opportunity for feedback and reassurance in a proactive way. Your manager sleeps better knowing what’s going on. Decisions get faster. Your wins start stacking.

“Micromanaged Lead”

A lot had changed when I took my third startup position. I walked into a lead role managing a team of two. Unfortunately, while the onboarding and team structure were a little more advanced, I joined right after the company lost two flagship clients, and somehow I assumed the responsibility. Leadership tightened the reins. Every move required approval, creating a demoralising, slow, confidence-destroying environment.

I learned quickly to stop fighting the constraints and instead build around them. I quietly took ownership of a problem and worked on a solution. Once I was happy with it, I sent a pre-approval message stating the problem, what I’d done, and the solution I was ready to action. This worked because it controlled the narrative leadership were working from. If they liked my solution, I got the go-ahead and built trust that I could take the lead. If they had alternative ideas, I had started the conversation, allowing them to add their two cents before I moved forward with it... but all within the scope I’d created. It was a win–win.

Sure enough, within two weeks I had taken back lead on all remaining clients, with leadership requiring updates only in team meetings and 1:1s. I then took this framework and applied it to those meetings. In less than a month, micromanaged approvals shifted from daily gatekeeping to weekly “thumbs up” reviews.

What I learned

Your manager brings the time; you bring the structure. Structure creates capacity.

👉 Action tip

Make the most of your next 1:1 with this structure:

• 3 mins → Recap / last actions

• 5 mins → Decisions first (one risk + your plan)

• 5+ mins → Growth ask (one rep, one next step)

Close with: “I’ll apply X feedback by Tuesday and loop back.” Then do it.

Wrap-Up

None of this felt flashy at the time. It felt much more like survival. But looking back, these three situations taught me the small, repeatable behaviours that removed uncertainty, made my progress visible, and cleared my path of hidden trade-offs and surprises. Run them consistently and your reputation shifts from “hard worker” to reliable problem-solver and with it, the person leaders trust with important problems.

This week, pick one story. Steal the action tip and see what changes.

Here’s to clarity in the chaos.

Until next time…

Hayds & The TSCA Team

P.S. If this helped, forward it to one early-career teammate who’d benefit. Small reps compound.

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