Doing Deep Work as an Entrepreneur: 5 Ways To Get Clarity and Boost Productivity

Nov 9

I just wrapped up my yearly business planning retreat, and this year was well — very different from all previous years.

Normally I go all "a beautiful mind" in my hotel room and cover the windows with post-its and brain dump mind mapping.

This was the first year I booked 3 nights instead of 2, and it turns out, I needed the extra time to decompress. Like stare out the window for hours kind of decompress.

After being frustrated with myself for not getting to it, I realized why this retreat was so different: I needed to do deep work instead of planning.

What Is Deep Work?

First, let’s talk about what Deep Work is. The term was coined by Cal Newport, author of Deep Work: Rules for Focused Success in a Distracted World. I read his book when I was in the midst of feeling anxious and unsatisfied with social media, and his thoughts and methods were soothing and actionable.

Deep work is the ability to focus without distraction on a cognitively demanding task. It's a skill that allows you to quickly master complicated information and produce better results in less time. Deep work will make you better at what you do and provide the sense of true fulfillment that comes from craftsmanship. In short, deep work is like a super power in our increasingly competitive twenty-first century economy.

In short — deep work is the key to getting more done in less time. But more importantly, it’s the key to getting the right things done that will help you achieve your goals and grow your business.

Why I Needed Deep Work

Since 2015, I specialized in digital marketing services for clients and entrepreneurs. In 2017 I niched into Pinterest management and marketing and provided that exclusively until mid-2022.

The seeds for pivoting my business from Pinterest to Business Mentorship started way back in 2020, but I was afraid to let go of my primary revenue stream and take the leap into something new.

Every other year my business planning retreat consisted of a little bit of deep work (i.e. goal planning and ideation of new products/funnels) but was mostly planning for marketing timelines, launches, and project management.

And as I stared out the window of my hotel room, gazing a the beautiful lake and stormy skies, I wondered why I had no desire or motivation to do any of those things.

The second day, I realized it was because I was moving into the unknown with my business — not just a new chapter, but a new book.

And what I really needed was to think deeply about who I want to serve, what I want to offer, and how I’m going to talk about my offers to my audience.

I spent 3 days crafting the foundation of my new business.

I sat next to the window and the fireplace, wrapped in a blanket with a notebook and pen, and outlined my customer, their journey, their struggles, and how I help.

I crossed out more taglines than I can count. I wrote and rewrote.

Not a single post-it was used. Not a single highlighter. Not a single calendar.

But I walked away from those 3.5 days knowing I’d done the most important work I could possibly do to help my new business grow and get seen by the right people.

Here are my 5 best tips for doing the best deep work you can do, so you can get clarity on whatever you’re working on, and boost your productivity knowing you’re working on the right tasks.

01. Be Flexible

Be prepared for plans to change and to shift what you’re working on.

I went into my business planning retreat thinking I was going to work on planning out the next year. What I needed instead was time to brainstorm and write 1st, 2nd, 3rd, and even 4th drafts of my new business messaging.

If you’re planning to do deep work on a project, just know that it might become obvious you’d be better served by working on something else more foundational or meaningful that’s key to your goals.

02. Set The Right Environment

The reason I go to a hotel for 3-4 days for my business planning retreat is that I am a wife and mom of Littles. This means that at any given time, something else other than my business could become a pressing priority.

I save for my retreat all year so that I can afford the best room in the best hotel around — complete with a lake view, a fireplace, a king-sized bed, and a step-down living room.

Getting out of your normal environment (your office, your normal coffee shop) is key to jostling those synapses in your brain around a little and opening you up to think differently.

Now, I’m not saying the only way to do deep work is to hole up in a hotel for 3 days, but you can make the effort to create a time and space to be undisturbed for at least several hours in a place that’s soothing and calm for you.

But the most important thing about your environment is setting yourself up to not be distracted.

03. Don’t Multitask

We all know by now that multitasking can negatively impact your productivity but it also burns way more calories as far as your brain is concerned — impairing cognitive ability (which is what you need for deep work).

Context switching, or multitasking, is when you’re jumping around doing multiple tasks at the same time, or during a single work session.

A real example from my normal everyday life would be when I have 30 minutes before the next meeting, so I try to call a contractor to schedule an estimate, catch up on LinkedIn posts from my peers, and sift through my email inbox at the same time.

Juggling 3 tasks at once might make me feel productive like I’m checking off to-do’s, but they are tedious tasks that are probably left half done at the end of 30 minutes.

The last thing you want when you’re in need of a deep work session (for a business retreat or otherwise), is to leave with a bunch of half-done tasks and a long to-do list.

True, meaningful deep work requires focus and presence with whatever you’re working on — an impossible task if you’re jumping around between different little projects and to-do’s.

That focus and presence can be achieved if you know the goal for your deep work session.

04. Set One Goal

Too often, entrepreneurs think they need to plan lots of goals for both their business and personal life.

If you don’t go into the next quarter or next year with a list of 10 goals and exactly how you’re going to accomplish them week by week, well then you just aren’t serious about success.

And while only you can decide how many goals you want to shoot for, or skills you want to build, or whatever metric you define as success — setting 1 goal for your deep work session and letting that guide your actions and thoughts, will set you up for achieving that goal in a much simpler and less-exhausting way.

Once I realized that I needed to rethink what I was going to do during my business planning retreat, I decided on one goal: to frame out the messaging and offers for my new business.

Over the course of the 3.5 days, I did multiple things to achieve that goal. They included:

Creating a Storybrand Brandscript for my new business.
Doing keyword research for my new offers.
Deciding on what offers were staying, and which were going.
Deciding on what marketing and platforms feel right for me (and my audience).

That was a lot to do in 3.5 days.

But each of those projects served to help me achieve the 1 goal for my business retreat.

If you are doing a shorter deep work session (1 day, or even 1 hour), then maybe one of those sub-projects is your only goal.

Either way, pick one and only one thing you want to accomplish with your deep work.

05. Take Breaks

At some point during deep work, your brain is going to stop functioning.

Some people call this cognitive ability — I call it my synapses stop firing.

You’ll know you’ve reached this point when you can’t stick to one train of thought, your output (ie, that new tagline) turns to garbage, and you’re just tired.

This can also show up as the scroll-hole or click-hole — where you’re just mindlessly scrolling social media or clicking between tabs on your computer and you can’t remember what you were doing 20 seconds ago.

Point of note: I reach this point every afternoon. I choose every day whether to take a break and recharge or to be done for the day (this usually depends on what’s going on with the family schedule).

During my business planning retreat, I took breaks by napping, meditating, spa appointments, and meals (I told you I save up for this all year!).

You cannot expect to put out the kind of quality stuff that happens with deep work for hours on end.

By recognizing when you need to take a break and charge your deep work batteries, you’ll end up being more productive in the long run.

Conclusion

The 5 ways I make sure I get clarity and boost my productivity through deep work are:

Be Flexible
Set The Right Environment
Don’t Multitask
Set 1 Goal
Take Breaks

When you’re able to lay the foundation for deep work in your small business, you’ll get into the flow with the super brainpower that leads to clarity about your business and decision-making, plus you’ll end up being more productive.