Taking an extended holiday or even a day “away from keyboard” can feel extremely stressful when you’re an online business owner. Even if you’ve communicated with your clients and prepped your team, leads will still roll in, calls will need to be scheduled for your return, people will join your email list and quality content still needs to go out to keep the momentum moving.
It wasn’t until I started the tradition of taking a month-long sabbatical with my family every August that I got serious about choosing tools and software that could run my business without me and where I could find time-saving resources that cut down on the literal hours I spent searching for, say, styled stock photography that didn’t feature corporate team handshakes and generic flat lays. (Why is there a ribbon, a camera, and a paperclip on that desk? What is this imaginary person’s occupation?)
It has taken me a couple of years and a LOT of free trials to find solutions that help my business run without, ironically, adding more work to my plate. But here’s the thing: I didn’t subscribe to all the tools all at once. I waited until it was absolutely necessary to make the time and money investment based on how my business was maturing.
Here’s how my business needs have changed over the years:
Back in 2018, I was a Dreamer, trying to figure out how my skills and interests could be combined to help other people and pay the bills. I DIY-ed everything in Google docs and that was it. Seriously.
In 2019, I became a Do-er. I touched every element of my business and set up and ran every tool and marketing automation. I went into it with the mindset that I needed to understand how everything worked before handing it off to someone else. Plus, I wasn’t bringing in enough consistent monthly income to afford outsourced help. Did I spend a ton of time on trial-and-error tactics and watch more YouTube videos in one year than my entire life combined? Yes. But it was worth it. #AlwaysBeLearning
Currently, I’m a partial Delegator but I’ve become savvier about the time I do spend elbow-deep in my business admin. To start, I took an *amazing* business financials course by Shanna Skidmore and mapped out my income and revenue goals including expenses. This meant having to get real about which business and marketing activities were bringing in enough ROI that I could start to outsource to other independent contractors. When Shanna challenged me to “time bank” my week and look at where I was spending my energy, I had to make a decision of whether I would automate, delegate, or eliminate tasks to make the cost of any business activity profitable.
(I’m not a Blueprint Model affiliate, but I am a huge advocate, and recently joined her private community The Money Club. It’s the tangible B-School meets CFO education my creative brain needs to run a real business that can pay for my girls’ school tuition. $$$$$)
Time-saving business tools for Dreamers, Do-ers, and Delegators.
The tools and resources that make the cut have stuck around because they’re easy to implement, grew with my business, and are worth the monthly subscription price because they save me time. The time I desperately need back so I’m not constantly finishing up new client proposals at midnight or trying to squeeze in digital product development during weekend nap times.
(P.S. There are a few affiliate links in here, but they won’t cost you anything extra. I use and highly recommend all of these products.)
Tools for Dreamers
90-Day Business Launch – When I decided to start my own business I knew I needed a roadmap and accountability to make it happen. I joined Michelle Ward’s 90DBL program and opened Big Picture’s doors with my LLC paperwork, name, core offering, pitch, marketing plan, and A LAUNCHED WEBSITE. Thanks to Michelle’s launch checklist, I booked my first client within hours of hitting publish. Big Picture would not exist without Michelle’s program. #facts
Creative Market – Ever wondered, how can I earn an income doing my hobby? Take a spin around Creative Marketplace to spark a few ideas. Look for “the gap” or something you feel like people shopping the site need, that isn’t being offered, or that you could do better.
Creative Live and Masterclass – Learn the skills you need to turn your hobby into a career or gain some insight into a profession you’ve always thought sounded interesting, but know nothing about. I loved taking Kelly Werstler’s class on interior design and learning how the environment around us tells its own story. Sara Blakely’s masterclass on entrepreneurship had me pausing every minute to write something down and even inspired my article on The 4 Types of People You Sell To.
Books – Yes, books. Coming from someone who is pro-fiction and really struggles to pay attention to (or care about) non-fiction or personal development, I can promise you the titles that made my Big Picture Branding Bookshelf at Bookshop.org will not bore you to death. PINKY PROMISE.
BP Bookshop.org Bookshelves
BP Dreamer-Friendly Workbooks
Audience Discovery Workbook – Nail your niche and get clear on the right offer for your audience and your entrepreneurial soul.
Brand Strategy MEGA Questionnaire – Make writing copy and choosing your brand imagery easier with a mapped-out brand overview that covers all your bases with brand excavation prompts PLUS the BP Signature About Page Primer!
Audience Persona & Brand Messaging Workbook – Learn to dive three levels deep into how your audience thinks so you can write compelling messaging that gets at your audience’s core and speaks to their problems in a way that nobody else does.
Tools for Do-ers
Tonic Site Shop or Squarespace – I started my website on Squarespace and believe it is the best place to start if you’re not a professional web designer. It has all the capabilities you want and can grow with your business. Design-wise I find it a bit more limited than the Showit platform. If creating a website that rivals a glossy magazine is #brandgoals then get run to Tonic Site Shop and you’ll never look back. Designers Jen Olmstead and Jeff Shipley are unrivaled when it comes to drag-and-drop-dead-gorgeous Showit website templates for the modern creative business owner. Jen’s writer-ly background lends itself to templates that are built with copywriting in mind (this is SO important) and they are no-code customizable.
Loom – The refrain goes: “This meeting could have been a Loom.” I get back hours of my day every time I send a client update or deliverable with Loom. As an introvert, I have to be fiercely protective of my energy and meetings are a one-way ticket to migraine-ville. With Loom I can share my screen and walk my clients through their decks and drafts, request they put their feedback in writing (via Google docs) or record a Loom of their own, and only after that will we set up some 1:1 face time.
When I first started to use Loom I was worried clients would feel distant or request outside meetings regardless, but instead, everyone reported back that it was a dream to be able to watch my walkthroughs and digest the information at their own speed so they could provide feedback that was thoughtful rather than reactive. Loom is especially helpful for my clients working a 9-5 who would normally have found it difficult to find a time to meet in between their job’s meetings and demands.
ConvertKit is SO MUCH MORE than an email service provider for my business. Yes, I use it to schedule and send out my bi-weekly Letters From Your Editor Newsletter, but I also use the ConvertKit Products feature to set up a mini-storefront to sell my digital products. Every newsletter subscriber receives a surprise discount on any BP Shop Product as a part of my subscriber welcome sequence. I use CK to process these discounted transactions and deliver my products.
⭐️⭐️ BONUS: Create your first email sequence with The Complete Welcome Sequence + Cold Subscriber Emails Templates.
Do you ever forget to send out client testimonials after your project or client has wrapped? Not on Dubsado’s watch. Dubsado is my go-to client relation management (CRM) tool. From the very first client inquiry to the 6-month post-launch emails (you know, where you check in on your clients and offer them a boomerang discount for a VIP session…) Dubsado lets you build out workflows that take 99.9% of the daily client admin off your hands! It’s also GREAT for teams and I can vouch for it, being a user as both an admin and a team member.
If you’re not at the stage where you can invest in your own brand imagery, Social Squares is the most modern-entrepreneur-friendly stock imagery site that lets you filter by color and serves up a curated roundup of images for your brand every month. Your subscription gives you access to the full library of thousands of modern and on-trend images, but the custom curation helps you focus your energy on what’s right for you, and steers you away from images that aren’t going to be on-brand.
Tools for Delegators
Plann – When you want to see what’s going on with your social media platforms in order to “sign and approve” what your contractors or team members have put together, Plann is comprehensive. The calendar features give you an at-a-glance look at what you’ve got going out and the content tags help you see if your content is balancing your core topics, like education, lifestyle, and product content.
Tailwind – Like Plann, Tailwind is a social media scheduling tool that can also be used by Do-ers, but it’s got really great reporting features and weekly email recaps that summarize what’s working and which needles are moving to give you that big picture overview. When you’re delegating, your job is to get out of the way and look at the overall picture. Pair Tailwind with Google Analytics and you’ve got a great window into how your pins and posts are affecting your overall site traffic and product sales.
Trello – I could have easily put Asana or Notion here, but I don’t have as much experience with Asana, and Notion didn’t stick with me. But I know a ton of people who use both and love them. Ease is what I’m after, however, and Trello is the project management tool of choice for the type of teamwork I do and the amount of onboarding and setup I’m willing to tolerate. I love Trello for setting up new projects and tracking progress. The color-coded tagging is simple and I don’t have to toggle between a bunch of options to find the information I’m looking for.