How I Email: Willo O’Brien, Speaker and Business Coach

Email is a non-negotiable part of everyday life. For some, it’s an unruly time suck, but enlightened email users have systems to ensure they’re not a slave to the inbox. We’re asking smart thinkers to give us a peek inside their inboxes, share tips, ideas, gripes, and everything in between.

Holistic business coach Willo O’Brien spends her days facilitating and supporting creative entrepreneurs through online programs, workshops, and individual consulting. Using her own business journey, she offers other business owners emotional and strategic support to help them thrive while working for themselves. Below, she shares some of her best tips for email management.

Interview by Jaclyn Schiff. This interview has been edited for length and clarity.

What’s your personal email strategy?

Simply put: Conscious Choice & Supportive Systems.

After realizing I had my own love/hate relationship with email, I made a conscious choice to shift my strategy so that my email works for me and not the other way around.

Especially as an entrepreneur, if any of my systems (email being one of them) aren’t working to support me and my business, and instead add complexity or unnecessary distraction, then they’re not serving their purpose.

Similarly, as anyone who is experienced in their field can relate, I may know how to manage email, but it doesn’t mean I have to manage it. As far as the business goes – not to mention my own wellbeing – my time is better spent creating and delivering content that’s supportive to my clients and customers than staring at my inbox all day.

With this in mind, I have a system that ensures my main inbox only receives the most relevant emails for me and my business, and I hired an assistant to ensure it all keeps flowing and nothing falls through the cracks.

Full transparency, sometimes things still fall through the cracks, but it all gets taken care of eventually. Plus, it’s way easier to stay on top of important emails because we’re not wading through a bunch of unnecessary clutter.

The key factor in all of this is first knowing how I want to approach email in my life & business (Conscious Choice), and supporting that choice with a system, which I share below.

You recently did a podcast episode about email overwhelm. Putting aside the tools you recommend, what are the one or two mindset changes people should make to avoid email overwhelm?

Like any relationship, if you’re not setting clear boundaries and honoring yourself (your time, energy, and focus), email can begin to feel invasive and become a belabored chore. This is when resentment grows, interest and attention wanes, and next thing you know, your inbox is an overwhelming mess you want nothing to do with.

The first step is to define the purpose of email in your life or business.

  • What are the emails you want to see coming in?
  • How do you want it to feel?
  • What actions are you committed to?
  • What’s the intended result of said actions?

With that purpose in mind, clarify your goals and your process to reach those goals.

  • Identify how your business functions (e.g. the sales/customer acquisition process, customer support emails, hiring and onboarding process, etc).
  • What’s your goal with those emails?
  • Clarify the process for each by creating a quick outline* that tracks the processes involved for each, and scenarios for various outcomes. *Remember, this doesn’t have to be complex! You actually already know this process intuitively, you just may have never written it down.

With conscious awareness around how your business operates, you can choose how you show up to it and how well it gets managed.

For example, I have consciously chosen that I do not want to be a slave to my inbox whatsoever. I’m not in the business of putting out fires, so I don’t treat the emails in my inbox as tasks that have to be completed right away.

We, of course, do our best to ensure all opportunities and current clients/customers are responded to as soon as possible, but I’m also not afraid to unapologetically delete an email or inquiry that isn’t in alignment or relevant to my business’ needs. Alternatively, knowing what my goals and priorities are, I can also Boomerang an email until a time when I know I’ll have more space to focus on it. I call this Conscious Procrastination. You always have agency and choice!

It’s common for entrepreneurs and small business owners to get personal and work emails in the same place. As an entrepreneur and business coach with a holistic approach, what do you think about having separate accounts for business and personal? Does it make a difference?

Yes, I think it’s crucial. Just like your business and personal bank accounts need to be separate, so do your inboxes.

After years of having the two co-mingled, I have now created a system that ensures my main inbox only receives the most relevant emails for me and my business, and it has been a game changer!

I now have clearly defined inboxes for each “department” and the purpose each of them serves. Mind you, I have a very small business, with no full-time employees (only contractors), but if you’re a solopreneur reading this, this still applies to you!

For my business, I have inboxes for me (willo@), my assistant, tech support (techteam@), customer service (support@), bookkeeping (books@) and a more general inbox (hello@).

Now here’s the key: almost ALL of my subscriptions go to a completely different Gmail address (and it’s a free gmail address, so I don’t pay for that one through Google Apps like I do for most of the other ones). There are some bookkeeping and tech-related subscriptions that go to that email, but NONE of them go through my main inbox. That is unless I know there’s a time sensitive offer – or it’s of such high value that I never ever want to miss one -m and therefore I consciously let it stay in my inbox. (There are very few of these, but they often relate to something I’m actively investing in – like a course or a community).

I do receive some personal email in my main inbox, but not very much. It’s extremely rare that it’s an actual letter from a family member or a friend and if that’s the case I welcome it in my inbox and can apply my same rules (respond, delete, or delay/Boomerang).

Most of the personal email we receive these days is related to personal interests, and these days our personal interests lead to subscription lists we’ve signed up for because of our various shopping habits, automatically enrolled in because we signed up through Facebook, things we’re working on learning or improving personally (health, relationships, personal finance, etc), invites or news related to social engagements or side projects — which should definitely have their own inbox.

It takes a little work to get this set up, and it doesn’t happen overnight, but it is SO worth it. You’ll be amazed at how much more peaceful you’ll feel knowing that most everything that arrives in your inbox is more pre-qualified to be relevant.

What’s the worst email behavior you tend to see in people and what should they do instead?

When clients come to me feeling overwhelmed, it’s often because they have no structure, boundaries, or systems in place – which is a recipe for chaos.

We must consciously curate the information we’re receiving, otherwise we’ll be blasted by a firehose and find ourselves drowning in a sea of distraction. This depletes our precious mental, emotional, and physical resources – which we need to make all the other important decisions in our life!

Taking a heart-centered, empowered approach to your inbox gives you room to create more space for the things you love doing. I’m not saying you implement a system like this and everything’s perfect, but I can tell you without a doubt that when you have clarity around the purpose email serves for you, and you’ve made conscious choices to support those intentions, your inbox becomes 10x more manageable.

May you all experience more presence and peace in your relationship to email!