Theo Robinson 🥉

Back when we burned CDs and printed photos, the only way I finished anything was labeling the sleeve with what got bumped. Same idea here: 'Happy to own this once A is finished on Friday. if it's urgent, which current task should I pause?' I repeat it in email the moment the conversation ends. Keeps you from drifting into weekend work because the tradeoff is on paper.

State a time limit and the reason. Example lines work best in the present tense. 'I have sixty seconds, then I'm finishing this deck.' Keep your hands on the keyboard and look at the screen while you say it. Stand up if you were sitting. End with a clear close like 'circling back after lunch.' At the machine, end the chat with movement. Turn toward your desk and take a step while you say 'heading back to hit a deadline.' If your hands are full, use your shoulder to point and start walking. If they continue, repeat the line once and keep moving. No apology is needed when you already gave a reason.

Totally okay to push back on meetings that could be handled async, and you can do it without looking disengaged if you frame it around helping the team move faster. Lead with value like I want to keep things unblocked and protect focus time, here is a way we can still share updates. When a recurring check in has nothing for you, reply with something like Not seeing anything on the agenda for me this week. Mind if I skip and read the notes, and if you need me tag me and I will join live. Send your update the day before in a Slack message or short email so you are contributing without consuming meeting time. Ask the organizer to mark you optional or to move the cadence to biweekly, and suggest a simple update doc where owners put status, blockers, and decisions needed before the meeting. Propose a rule of cancel if no agenda 24 hours ahead, or only hold the meeting when a decision is needed. In Google Calendar you can mark yourself Optional, click Propose a new time, or Decline with a short note, and in Outlook you can do the same plus use Scheduling Assistant to show conflicts. Block Focus time or Working hours on your calendar so auto invites land on top of protected time and give you cover. Try it as a two week trial and then share that nothing slipped and your turnaround improved, and keep attending 1 on 1s, planning, and decision reviews since those are rarely good email substitutes.

In a flat org, don't ask for a "promotion," ask to align scope and compensation with impact. Go in with a one-pager of simple numbers and outcomes: the projects you led and what they delivered (e.g., 3 launches that brought in an estimated $120k, or cut churn by 2%), the hours you freed up (took over X process saving ~10 hours a week), and the training impact (onboarded 2 hires, reduced ramp from 6 weeks to 3). Put a before/after next to each item so the benefit is obvious, and include any manager-like work you're already doing, like coordinating timelines or quality checks. Then say, "I'd like to talk about my scope and how to reflect it in title and pay so it matches the value I'm providing." Offer flexible options so it's easy to say yes. For title, propose something that fits a flat org without creating hierarchy, like Senior [Role] or [Function] Lead, or even Acting Lead for the next 6 months. For pay, give a clear target grounded in market or impact, for example, "Given the added responsibilities, I'm looking for a 7–10% adjustment," and then present alternatives if budgets are tight: a smaller increase now with a dated review, a one-time bonus, equity grant, or a professional development budget and 2 extra PTO days, tied to the same milestones. Ask what specific results would unlock the full adjustment, write them down, and agree on a review date in 90 days. Close with, "I'm committed to the team and want to keep taking this work on; help me make sure the role, title, and compensation reflect it," then follow up with an email summarizing the numbers, agreed milestones, and the review date so it stays positive and concrete.

It's absolutely not too late; lots of people break into IT support in their 30s and 40s, and managers prize maturity and customer skills. Your hospitality background screams patience, de-escalation, and clear communication, which is half of help desk. If you want a single credential that actually moves the needle, aim for CompTIA A+; if money's tight, self-study and pass once, don't stack a bunch of certs. Pair that with working knowledge of Windows and macOS support, basic networking like TCP/IP, DNS, and DHCP, Office 365 admin basics, and Active Directory user and group management. Nice-to-have later would be Network+ or ITIL Foundation and a bit of PowerShell, but your priority is A+, hands-on practice, and communication. To translate hospitality on your resume, quantify what mirrors help desk: high-volume queues, time-to-resolution, NPS or CSAT, training new staff, shift leadership, and documented procedures. Phrase bullets like you triaged issues, documented steps, escalated appropriately, followed playbooks, and turned fixes into repeatable SOPs. Add a small home-lab section showing concrete work: spin up a Windows Server VM, create a domain, make users, join a client, set up file shares and printers, test group policy, and practice with a ticketing tool and remote support software. Realistic timeline while working full-time is about 8–12 weeks to study and build the lab, start applying by month two, and expect 3–6 months total to land a first role, often with an MSP, internal transfer, or short contract. Network with your company's IT, be flexible on shifts, and prep a simple troubleshooting story framework (identify, isolate, test, document, escalate) so you come across as reliable even without prior IT titles.