Jack of all trades, master of none?

The idea of being a solopreneur has a certain level of allure to it. You're promised freedom, the chance to pick your own hours, and the opportunity to follow your own creative pursuits. Sounds great, right?  In addition to the benefits however, there are drawbacks that many solopreneurs face in their entrepreneurial journey. For one, you must be willing to shoulder the risk yourself as an individual worker. You can't fall back on colleagues because you're working alone.  An entrepreneur may have surrounded themselves with a team skilled in a variety of areas, especially those that are outside of areas they want to specifically work on.  As a solopreneur, you are, at this moment and by definition, on your own here.

And that’s a bit of the crux outlined in On Being A Solopreneur: Part 1 of this blog.  You have no choice but to take on more risk since you must “wear many hats” as part of growing your business (marketing, product design, accounting, you name it).  If you don’t identify which hats you love and which you avoid wearing, you take on even greater risk since you’ll not place the necessary focus on those avoided tasks in your day-to-day work.  You’ll also need to figure out how to “look good” in each hat you wear, whether you enjoy wearing that hat or not. 

To continue the metaphor, what if there’s a hat you seldom need, or don’t even know you need?  If you’re caught in certain situations, such as being in a blizzard for example, it would be helpful to be able to put on some winter-friendly head wear.  Having the right winter gear could even help save your life.  (At the very least, who likes having a cold head in a snowstorm?)  It’s reasonable to acknowledge that you will need to be prepared for such occasions, but what if you didn’t know a blizzard was even in the forecast?  What if you didn’t even know what a blizzard was? 

Let’s say you live in Florida.  Needing a toque is so far out of the realm of possibility that even if you know what to wear in a snowstorm, you probably don’t have one in your closet!  Putting it plainly, if you discover you require expertise in a particular topic area essential to doing business, you’ll need to be able to recognize this and educate yourself quickly.  Needing help for things you didn’t expect or hadn’t even heard of is likely to be part of your solopreneurial journey.

Whew!  Who knew hats could be so complicated?

When you, by choice or necessity, wear all the hats, the continual switching from hat to hat (role to role or task to task) can also take up more time than you think.  If you are like most solopreneurs, these business hats aren’t the only ones you are wearing either.  You likely have a mom hat, a dad hat, a son or daughter hat; the list goes on and on.  Adding every single business role to your job description becomes a very large number of hats indeed.  For most solopreneurs, being your own boss and setting your hours around other commitments in your life, including school or raising children, is worth it for the promise of obtaining all the potential payoffs when you reach your goals.  But that doesn’t make it simple, not at all.

That leads us then to the next questions:  how do you keep the right kind of hats available and how do you use your time well when you’re faced with so many hats on and off your head all day?  How do you avoid spending too much time becoming a subject matter expert in every area of your business that demands your attention but enough time to get everything done and not only done, but done well?  In other words, how do you avoid that “jack of all trades, master of none” syndrome?  How do you dive deep enough into what matters without neglecting the stuff that ensures you stay on track to accomplish your business goals?  How do you manage to pivot quickly without getting mixed up with what hat you have on at that moment?  

What helps is figuring out a way to organize and keep track of all the stuff you work on in your business.

Task management for Solopreneurs is no simple task!

Task management for solopreneurs is a necessity. It’s not enough to know what you want to do, but also when and how to do it, and that's facilitated by creating a system that enables you to track all of it and get it done.

To begin, you will benefit from looking at your day as a series of half-hour time/task blocks that reside within three time periods: morning, afternoon, and evening.

Where to start?  Start with a goal.  Shape the goal into a plan.  Break the plan into tasks (task management).  Break those tasks into approximately half-hour long chunks so you can use your time on a budget (time management).  This enables you to figure out how much time doing each task is going to take.

Make a giant list of all the to-dos and start with that. 

Each evening (or the time of day you feel best suited to you for planning) write down the single most important task you want to accomplish the next morning, the single most important task you want to complete in the afternoon, and again the single most important task you want to get done in the evening.  Try to ensure that each task will realistically take only one to two hours maximum to complete. (And know your habits – if you chronically underestimate how long something will take, double or even triple the time). If your task is something you feel will take 17 hours, you haven't broken it into small enough chunks.  Even a book is written word by word, sentence by sentence.  How much do you usually write in half an hour?  Make that your task.

Repeat this pattern every single workday and focus as exclusively as possible on those three things.  You’ll fit your other tasks in around this pattern.  However, just this simple process can significantly move you forward because you will be working on the tasks that make progress to reaching your goal. 

As a bonus, a strategy like this provides a significant amount of motivation.  Ticking off that one box for the must-do task every few hours is going to solidly move you along on the good habit of doing.  (Rather than just thinking about doing, or thinking you need this or that to get started doing.)  What needs doing in the future will become much clearer over time because you’re in motion.  If you think of it as driving along a road, you can't see where the upcoming turns are until you get closer to them.

What to do if you end up with extra time?

If you get the one most important thing done early and want to choose something else to work on, bump up the afternoon’s task.  If you get that done too, move on to the next task. Don’t just move on to lesser tasks, aim for the 3 most important things first. Additionally, it’s very likely that one of these tasks will end up taking longer or some obstacle will pop up preventing you from getting it done.  Be prepared to substitute for a task that you can do in the interim while you wait for everything to move into place to support completion.  Always have one or two tasks in the wings ready to fly in as needed so you don’t find yourself wasting time trying to figure out what to do next.

Fitting it all into the day, how is that done?

What if you have a task that typically takes 5 minutes, like replying to an email?  Simply plan to reply to emails in a half-hour chunk, during the time of day that best suits that task.  Half an hour then is (let’s say) 4 - 6 e-mail replies (allowing room for any interruptions or emails that might take longer).  Or perhaps you have a task that takes 1 hour.  Find a way to break it into it measurably smaller pieces or simply budget two chunks.  So, for example, a print-on-demand design typically takes you one hour to create the graphics.  Budget two half-hour chunks.  If you don’t know how long each task takes, it’s time to find out – time yourself doing what you do daily and come up with reasonable averages. 

Of course, there are lots of other things that will demand your attention.  Capture all these to-dos in a tool or on a piece of paper so they aren’t lost or forgotten. Note the patterns and budget time for these tasks too.

Don’t neglect to make time for all the other stuff though!

Make sure you have a block of time each day to check emails, return phone calls and review the day. You would benefit from having at least a day a week where your business is not on the task list, such as a Saturday or Sunday, where your family or other interests take precedence.  Schedule one full day a month for administrative tasks and schedule another day a month to just do nothing and take a day for yourself.  Balance is an important part of being successful, because it helps you stay fresh and focused.

Keep in mind that this is a fluid process, and that you don’t live in a perfect world where a list will provide all the answers.  This process is a way to start taking more action and building in accountability to your system, an accountability that can serve your overall goal of making more online.

Tracking your tasks – how to make sure you don’t forget stuff!

So, what are the best ways to manage all these tasks? What should you prioritize? You will note that most solopreneurs (at the very least) use a task management app to keep track of what they need to do.  There are plenty of task management tools out there, such as Todoist, TickTick and Microsoft To Do.  You’re not going to find a review of them here, but most of these apps have free trials or in the case of Microsoft To Do, is free with the Windows operating system.  To know what app will suit you best, block out a half-hour task and then you can set up a free trial to assess the paid ones. 

You can also consider using project management apps, such as Basecamp, Freedcamp, Trello, Asana, Microsoft Project and many others.  But it’s important to not fall into the trap of thinking you need any particular tool in order to get started. You don’t.  And it’s important to try to avoid the trap of just working in the project management apps themselves without working on tasks that improve your bottom line.  This is a place where many folks end up stuck; you basically lose time because planning can be a safer space than actually putting your real ideas out into the world.

If you have no budget for any of these types of tools, a pen and paper are going to be your best friend.  You have at least that.  You can use the note taking tool or sticky note app that also is a part of your computer operating system – both Windows and the MacOS have one.  Don’t let a “I don’t have this software” thought stop you from getting something done.  There are always alternatives. Try not to spend too much time being concerned with what you lack, focus on what you have as tools to keep your tasks in order and, by extension, keep your time well-budgeted.

Time management for Solopreneurs

As you’re seeing, the flexibility of self employment can be messy and comes with stuff to-do, stuff to know, hats to wear, and the list gets longer still.  As a solopreneur, you are in business for yourself, but you are still in business. This means that you’re going to be faced with the challenge of not just managing tasks but managing your time knowledgeably in order to get projects done - whether it be completing an assignment for a client or finishing up work on your own product or service.

There are only 24 hours in a day, and no one feels this reality more keenly than the solopreneur.  There seldom feels like there’s space where you get to just “close shop” and not consider your business. Working from home compounds this since your computer is only steps away.  It’s sometimes far too easy to sit down and work for another hour.  You need to get stuff done but also retain balance.

Let’s tackle how to use look at time too.  Tasks are simply those one-by-one items that need to get done in order to complete projects.  Projects are simply plans that help you reach your goals.  It's easy to get caught up in day-to-day tasks and forget about looking at the plans that help you stay on the path to your goal.  You can straight-up forget to focus on the things that matter and get stuck in work that doesn’t contribute to your bottom line.  If everything you are working on for days in a row is stuff that’s not putting money into your bank account, your business will not be viable.

A technique that works well with the task management strategy above is a time management strategy called the Pomodoro Technique.  The Pomodoro Technique, developed in the late 1980s by Francesco Cirillo, is a popular time management method, and it’s used by millions of people around the world.

The Pomodoro Technique is based on four key principles:

  • decide on what you want to work on for 25 minutes at a time, called a Pomodoro
  • take a 5-minute break after each Pomodoro and a 20-30 minute break after the 4th pomodoro
  • the technique can be applied to any task that requires sustained attention and consistent effort (i.e.: writing, programming, studying, etc.)
  • the technique is also beneficial for organizing smaller tasks together into manageable time chunks to keep you focused on one thing at a time rather than jumping around from small task to small task

When you use the Pomodoro Technique each day, you’ll get in two, possibly three significant work chunks each day.  And if you can manage to work specifically on tasks that improve your bottom line for 4-6 hours a day, you are exceeding 90% of solopreneurs right there.  Pomodoros are simple and that’s part of the beauty of it – you set the timer and go!  (I'll dedicate a future article to this topic and link to it here when it's online.) 

So, to summarize:

As a solopreneur, you need to be the SME (subject matter expert) in many of the tasks associated with your business, and since you are the only person doing the actual work of business-building, managing your hats, tasks and time well is essential to your focus, motivation and eventual success. 

First up, identify what goal you want to achieve.  It can be a financial goal or other goal that’s tangible to you, such as writing a book.  Next, you will define a project (or series of projects) that you think will take you to that goal. Those projects will break down into a series of tasks, and you’ll define a task roughly by the half-hour. (Longer tasks can be defined as multiples of the half-hour if it’s impossible to break them into half-hour chunks.)

Daily, you’ll choose the three most important tasks you want to get done each day, and most important ones are defined as the tasks that get you closer to your goal.  To execute those tasks, you can use the Pomodoro technique to structure your time and maintain focus.  When you get the first task done, move on to the second.  And, to get all the rest of the stuff done that’s required for your business, turn them into half-hour chunks of time as well and plan to spend a day each week or each month tackling them too.

You’ll get there

About the Author Irene Fulton

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