Deep vs. Shallow Work

When I worked for someone else it was always fun to plan out my days. I had my marching orders from the COO in terms of long term projects and objectives. But I also had my team to manage and any number of meetings to attend. Those expectations allowed me to break up my days into deep work (thinking, planning, visualizing) and shallow work (meetings, emails, administrative tasks). The ideal entrepreneur schedule is not so easily constructed. But it can be. When I think about my time working in an office it was a lot more shallow work, and far less deep work. As a member of the leadership team I was expected to be in meetings most of the day and it was my team who were busy doing all of the “real work”. And when we think about work, the only work that feels “real” is the deep kind – the producing kind. The admin tasks – meeting and talking and collaborating is tedious and produces small day to day gains. But the ideating and vision casting is a different kind of work – and often the most meaningful. It fuels the execution of all other aspects of the business. And yet, it can be the last thing on our calendar.

Meetings Are The Worst, Email Sucks Too

Meetings for the most part are a a fail in most businesses. Research has shown executives are spending 23 hours a week in meetings on average. That’s 1100 hours a year (46 whole days) assuming you take 4 weeks vacation at some point. And if you and your colleagues aren’t masterful communicators (most people are not), most of that time will be spent with people talking over, and around each other, instead of truly communicating. Have you ever been to a meeting, and found that when you left you still had no idea what the next steps, conclusion or decision was? Yeah, me too. It’s the worst kind of feeling to realize you have just spent the last 30, 60, 90 minutes of your life trapped in a room and nothing productive has resulted from it. Of course, there are some phenomenal communications courses on how to map out meetings and communicate more effectively. But the bottom line is communication is always a team sport, so if you want your shallow work to be better, you need some wraparound strategies and norm setting on how messages are sent and received. Meetings are only one of the many things that eat away at a our execution time as workers. Email is another big time suck, and largely is a bigger waster of time than meetings. People usually send an email as a way to get out of a face to face conversation. And I guarantee you, delivering a message via email message is even less effective than a long drawn out meeting.

Taking Your Business From Shallow to Deep

So, here’s a nod to the executors out there. As a solopreneur, many of us start off by doing a lot of the execution. You are your first admin, and rightfully so. If you are a one woman show, there really is no other option. But as you grow, and eventually as you want to scale, you have to start thinking about how you can step away from the busyness of execution. Your goal is to get into the visionary place much more. You want to live in creative land and be the Chief Innovation Officer. This means that your daily responsibilities and entrepreneur schedule should start to shift and change. As a solopreneur myself, I found that as I started to find what was working in my business, my attention had to be pulled into those deep areas and out the tedious shallow minutiae of day to day. So, how do you know when it’s time to start delegating, and what to start delegating first? What does the ideal entrepreneur schedule look like?

Branding, networking, freebies, mind the money, and build consistent content

Of course, there are no one size fits all answers for this question. The key is to first learn your business and all its execution pieces well enough that you can delegate in the first place. And then once you know those pieces that fit into your 20% of work that yields 80% of your results, you start identifying what you absolutely have to do yourself. These are things that make top priority on your calendar. All the other pieces, may still need to get done, but instead of you executing it, you can hire someone else to do it. And you manage their process, leverage technology to automate it, or stop doing that thing alltogeher.

The Admin Phase

Starting Out – Months 0-12 Know enough to be dangerous. Great leaders lead from the front which means, you have to set the standard for what you expect from your team and your company. The best way to understand what reasonable standards are (they should be SMART just like your goals) is for you to experience them first hand. Here is my shortlist of things you should be focusing on as a business owner in your first year.

  1. Building Your Brand – You have to do the work of nailing your elevator pitch. Only you can pinpoint the exact thing you do for the exact right customer. Getting this piece right is the key to all of your other success. You have to spend the time understanding who your clients are, and why they are coming specifically to you for their products and services needs. I recommend when you are first starting to pitch to answer the question “what do you do?’ as often as possible. Not sure where to start? Try this 5 minute primer video on pitching to get your mojo flowing.
  2. Get Social – Networking has always been a staple of business. but as a solopreneur its even more important to get your face out there. If you are telling people what you do face to face with your elevator pitch, the next step is to start reflecting that in other social arenas as well. Pick 2-3 platforms that you love to be on and learn them! Not sure where to start? Start by optimizing your Linkedin. When I walk clients through setting up a profile there are 13 steps to really getting your LinkedIn looking like you are about something. You can check them out in his cheat sheet. It’s all about putting yourself out there.
  3. Do Some Gratis Work – Volunteering is a great way to continue to get your face and brand out there. When people know you are willing, and able to help them, they are more likely to come to you first for (paid) support. I did a lot of this in my first year of business and it continues to pay off in big ways.
  4. Manage the Money – There are tons of free software programs for bookkeeping to get you started on owning a business. But one thing is for certain, if you don’t set some financial goals for your business, that’s a good way to get nowhere fast. Just like in personal finance, not having a budget is a good way to let the coins leak out of your pockets. Learn to budget, and check out opensource and free software for managing your books like Wave or Freshbooks. Remember if you are just starting out, run lean and keep expenses super low. Don’t go crazy and hire a bookkeeper and get Quickbooks subscription until you know you can easily afford it each month
  5. Website & SEO Stuff – You don’t need a fancy expensive website when you are starting out. You can start with a landing page like Leadpages (a one page website) that will help you capture potential client contact information if you are in the micro planning stages of building your biz. If you are a little further along, consider grabbing a blog page from WordPress as they are great for making websites plug and play. WordPress is easy to self manage and most importantly free until you move over to the paid platform. Learning how to generate content on your site and make sure you are optimizing it with keywords, will help you focus on what you want to talk about, help you build that consistency muscle with building content, and help you find your voice (super important for your first year as you are defining your brand).

Those are my top 5 for starting out. This is of course in addition to providing your primary service (given) but if you stick to these things in your first year, you should have a solid understanding of your business in about 12 months time: Branding, networking, freebies, mind the money, and build consistent content.

The Admin Entrepreneur Schedule:

What does all of that look like in real time?

Marketing Mondays

  • 2 hours writing or editing a blog post, optimize it and post to your blog/site
    • Cross promote your top social media channels, dropping links and using long form posts to capture the attendance of your ideal clients avatars
  • 1-2 hours – create and schedule out the rest of your social media calendar using a tool like Hootsuite to post for you during the week.
  • 1 hour over the course of the day checking social media and engaging with followers, commenting on other posts, making new friends, links, follows and responding to any responses to what you have posted that day.
  • 1.5 hours of service providing/prep – email check, client research, follow up emails etc.
  • Study up on marketing by taking free courses on a trusted platform like Hubspot so you can be constantly thinking of new ways to leverage new tech in your marketing strategy.

Tuesdays, Wednesdays, Thursdays

  • Write for 30- 45 minutes a day
  • Provide 4.5 hours of your primary service
  • 1 hour, social engagement and networking

Finance Fridays

  • Write 30-45 minutes
  • Invoice any work for the week. (Enter Paypal, Freshbooks or Wave apps)
  • Upload receipts for any business expenses you have incurred that week (write what the expense was on the receipt and take a pic and then upload to the cloud in a folder for the month and year of the expense)
  • Take a look at your profit and loss statement and make adjustments for business budgeting based on what you see.
    • Can you make payroll/pay yourself for this week/this month/next month?
    • If not, what do you need to do?
    • if You can, how did that happen and can you replicate it/double down on that result?


  • Rest


  • Prep for Monday marketing (Choose a writing from during the week and start to edit it to fit your brand, include keywords)

The Growth Phase

Months 13 ish – 36 (when you set a consistent salary til next product/service launch) After your first year in business, you can start to delegate some of the stuff that’s making you money from your personal effort. This is where you can leverage something like the Covey 4 quadrants to see what’s really important for you to keep on your plate versus what you can delegate out. Start delegating and manage someone else to do the stuff you have mastered in quad one. Now you start focusing on quad 2. Here are my top items to start managing instead of doing.

  1. Bookkeeping – Hire a bookkeeper. At this point in your business you should be turning or close to turning a profit and paying yourself a modest salary. This is a good time to let someone else handle your books. A professional bookkeeper will make sure you are tagging things correctly come tax time. They also help you manage payroll, paying contractors, and help you see where the money is going. You will still have some time in the week for finance, but instead of you doing the invoicing, and receipt reconciling, this can turn into you checking in with someone else. YAY for found time.
  2. Marketing your content – This is where you could hire someone to manage your content calendar. You will still be writing every day during the week and posting to your blog or creating other content for your podcast or video channels, but the contractor you hire to manage Hootsuite or other content scheduling tool, should be able to emulate your voice through what you have produced in the last year. This will help you to step away, and manage them through the very process you have perfected in the last 12 months.
  3. Social Media Engagement – Don’t give this one entirely away. You can hire a VA or community manager to mange things like a community Facebook page, business Facebook page, or your following on IG. If you have someone doing some of the day to day work, make sure you are still popping in from time to time to talk to the people, check the DMs, and engage. This would be a good time to start incorporating video into your marketing if you have not already. Using live streams is a great way to boost SEO and keep your audience connected with you and the brand, even if you aren’t checking all the channels everyday. One thing I don’t recommend you delegate away is your LinkedIn profile because it is so intensely personal. Because LI is still a platform that recommends you only accept links from people you actually know, it doesn’t make sense to delegate this one away. More on how to leverage LI on the go can be found in the cheat sheet on optimizing your page.

So what are you doing now that you have pushed out most of your Monday through Friday work? This is where you really start to step more into your visionary role. After 18 months or so, you should have a good sense of where your customers come from, what they like to buy, and what services and products give you the most bang for your buck, Through networking and volunteering you have positioned yourself as an authority and are probably getting people reaching out to you directly in your inbox, LI messages, and on your site. Now is a good time to start thinking about new product development and how you can double down on what’s working.

The Growth Entrepreneur Schedule:


  • 45 minutes – 2 hours to write and edit new post
  • 30 min – 1.5 hour check in with marketing team, review scheduled posts and approve, provide feedback
  • 1 hour learning new business skills
  • 2 hours meetups and collaborative meetings
  • 3+ hours new product development

Tuesdays, Wednesdays, Thursdays

  • 45+ minutes creating content
  • 2 hours+ new product development
  • 4 hours service delivery (in your 80/20)
  • 1 hour email check and follow ups


  • 45+ minutes creating content
  • 1.5 hours website updates
  • 1 hour bookkeeping and finance check in meeting
  • 2 hours collaborative meetings and fielding partnerships
  • 2 hours+ new product development


  • Off, Rest


  • Edit new content posts for the week
  • Edits to goals and long terms plan
  • Plan the week

If you are new to entrepreneurship, or side hustling and are worried about building your brand, getting started with LinkedIn is a great way to get the ball rolling. Changing your headline and starting to think about your pitch all work wonders to attract and start conversations with others who are interested in what you do. Here’s that free LinkedIn guide if you missed it. As a business, owner it can be overwhelming to think about all the little things you have on your to do list, but starting is the hardest part! So here’s to getting started and going deep!

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