Looking back at your freelance journey, what is one tool you wish you had found in year one instead of year five? The one that would have saved you the most time, money, or stress?

Honestly, Grammarly. I wish I had it in my first year. It would’ve saved me so much time fixing small writing mistakes and overthinking my wording.

On 6/21/2026 at 2:30 PM, Barn said:

Honestly, Grammarly. I wish I had it in my first year. It would’ve saved me so much time fixing small writing mistakes and overthinking my wording.

I used this for a number of years and it was so helpful. I am usually good with grammar but I often overlook things with proofreading. This would catch it every single time. I think there were privacy concerns or something though. I can't remember. There was a reason I stopped using them.

Loom. Recording a two-minute video instead of writing a ten-minute email. Clients understand faster. Fewer revisions. Less miscommunication. I wasted years on text-based explanations.

@HannahK Loom is great for explanations. Terrible for documentation. I wish I had discovered Notion sooner. All my client notes, project plans, and content ideas in one place. I spent three years searching through email threads.

@DerekNoBS @HannahK I wish I had found Calendly in year one. The back-and-forth of "when are you free" emails probably cost me fifty hours over two years. One link. Done.

@SamC I am still doing the email dance. Is Calendly free or paid? I am early stage and watching every dollar.

@Jenna Torres Free tier is enough for one event type. Paid is worth it once you have multiple offer types. Start free. Upgrade when you need it.

@SamC @Jenna Torres I will add one more. Zapier. Automating the repetitive tasks between tools. When a client books via Calendly, it creates a Notion page, sends a Slack message, and adds them to ConvertKit. One trigger. Four actions.

@DerekNoBS @SamC @Jenna Torres @HannahK I am implementing all four this month. Loom for explanations. Notion for documentation. Calendly for scheduling. Zapier for automation. Year one me would be jealous. Thank you all for the recommendations.