Working Alone: How to Structure Your Time


Photo by Bethany Legg on Unsplash

In limits, there is freedom.

— Julia Cameron

You’ve left your corporate job to start your own company or you’re fresh out of school and looking to launch yourself. Maybe you lost your job and worry about what’s next.

This can be scary, even overwhelming. You’re not sure where to start. You’re not alone, lack of structure is challenging for most people.

But step back, take a deep breath. Recognize the unbelievable freedom you have. Your life is yours.

Feeling that freedom is there. It’s not that far away. Start small, stay consistent and committed, and use strategies that hold you accountable when you most need it.

Let’s dig in.


Step 1: Get your vision right

You probably already have an idea of what you want to achieve, you might even have specific goals and sense of the activities that will help you reach those goals.

Your goals or your notes might be something like “ write and revise remaining chapters of my book,” or “apply to grad school” or “get a job.” Those are all helpful insights, but consider them information, values if you will. What you still need is a vision statement and 30–60–90 day goals to clarify the best solution to the problem you’re trying to solve.

Why take this approach? Three reasons:

1) A vision statement and 30–60–90 day goals are global, forcing you to summarize all that you want to do in one place.

2) It frames what you’re doing in the positive.

3) It makes your work sound important, because it is.

List out what’s ACTUALLY important to you

In the examples above, I mention mainly career-related goals. For many of you, those are really prominent, but they probably aren’t the whole story.

If you have unstructured time, you likely do care about your career, but you probably care about other things too, like exercising x times per week or visiting friends nearby or a million other things. Again, you are free. You want to use this time wisely.

Let’s say for example you know you want to learn JavaScript and a few other front-end development skills to get a job as a developer. You start on that path and a week or two into it, you feel a haunting guilt related to your family or your friends, or to how you’re eating. That’s no accident. That’s you identifying what you value. You are more than your programming skills.

Give yourself credit for making progress on all the things that matter to you.

Here are some questions to answer to draw out these values so your vision statement captures ALL that you want to achieve:

  • In 3 months, what will be different in my life that would make me proud?
  • Who are the people that I really admire and wish I was more like? What things do they do? What activities do they not do?
  • Knowing what you know now, if you could write a letter to yourself that you would receive exactly one year ago, what advice would you give?

Hang on to this. This is a summary of your values. Keep these responses as a living document. I keep mine in a google doc. This will change over time. You’ll want to track it.

Write your vision statement

Ken Schwaber, a major contributor to the agile manifesto, defines the vision statement for us: “The vision describes the project being undertaken and what the desired end state is.”

Your vision is your anchor, your northstar, your golden rule.

Write something and try it, start somewhere and keep working on it. The clarity will come. What’s most important is having a vision of the future and what will be different and why that’s important.

As Adam Grant says, have the “willingness to act on the best information you have while constantly doubting what you know” — Knowledge@Wharton Interview

A vision makes you identify what will be different and for who. This will contextualize your efforts. It changes the conversation in your mind during planning from “here’s a long list of everything I have to do” to “what’s the minimum I need to achieve to start seeing success?” Spend some time researching vision statements online if this still feels confusing to you.

Now that you have your responses to the questions above, answer the questions below. If you don’t know one, skip it and go to the next. Revisit the harder ones at the end:

  • Who is your target audience? Who stands to benefit from this work?
  • What problem(s) will the work you’re doing solve for them?
  • How will you solve those problems?
  • Why is it important to solve those problems?
  • Once we have solved those problems, how will things be different?

Andrew Burrows, an incredible agile coach I worked with as IBM for years developed a similar set of questions that I’ve adapted here to better suit a solo-working model.

Now I’ll go through an example showing how this works:

While writing this, I am taking 5 months off from work to build my data science skills and become a yoga instructor.

Here’s my vision statement:

I will be successful if, by the end of 2017:

  • Yoga studio(s) in the New York area can hire me as a vinyasa teacher since I have the necessary skills, connections/relationships, time, and certification to conduct yoga classes.
  • Leaders in tech companies seeking to improve their internal communications through data-driven methods understand I have the skills and experience necessary to set up and/or run an automated, integrated system and they understand it is a groundbreaking technology in change management and information flow.

For more help on creating a vision statement, read this article that describes creating a vision for product development.

Outline your 30–60–90 day goals

I’ve worked with a number of incredible agile coaches in my work at IBM, who taught us to plan our work in 30–60–90 day goals.

Why block it at 3 months?

1) It’s really stressful to think about more than 3 months at a time. Be nice to yourself.

2) It’s unlikely the world will stay consistent enough and/or that you won’t learn things that affect your overall goals.

It’s helpful, too, to have these broader goals with regular chunks of time to give you benchmarks for how you’re doing. This might feel like a restrictive process if it’s new, but, it will give you freedom once you get into it. This is a lot easier than listing off 10 things you’ll do each week. It’s also easier than planning out a full year or God forbid, 5 years.

90-day goal

Do this first. This is a somewhat more practical version of your vision statement, so it’s an easy place to start. Take your vision statement, and your response to your the question about “In 3 months, what will be different in my life that would make me proud?” Write 1–2 practical sentences that summarizes what needs to exist in 3 months time in order for your vision statement to become true.

Keep it short, keep it high level, keep it clear.

Here’s my 90-day goal:

In 90 days, I will be 2/3rd’s complete my yoga teacher training and have a list of studios I’d like to teach at, I will be solidifying the new job role I’ll take on in 5 months time (if not sooner) and finalizing last details, and I’ll be clear on when I’m wrapping up my current projects.

60-day goal

Reflect on your 90-day goal. Now ask yourself, in order to reach that 90-day goal, what needs to exist in 2 months time? A key question to ask yourself is not “oh, look at all that stuff that needs to be done,” but instead, what is the minimum that needs to exist in order to reach success? Research the 80–20 rule if you’re not familiar with it. It’ll help you hone what’s valuable and what isn’t. You want to get the bare minimum up and running so you can keep refining it.

30-day goal

Like your 60-day goal, reflect on what you need to have done in 1 month’s time in order to meet your 90-day goal. To help, I’m including another example from my current experience:

In 30 days, I will have the ability to conduct basic data analysis in python using statistical methods. I will be engaged in a for-profit and/or a non-profit project to begin building my data science portfolio and have a practical application to focus my continued learning. I will be engaged in a yoga teacher training program and have a broader sense of how this work can make a difference so I can begin to see how else my education should grow.

Now that you’ve got these three sentences goal-statements, take a few minutes to consider: Is the 90-day goal something that would make you feel successful for that amount of time? Is it reasonable? If not, adapt it and the other shorter-term goals.

Be real honest with yourself. Can you do all that’s required in order to meet that goal? Are there external dependencies that affect your ability to achieve that?

Edit it to make it possible. You want to be successful here, not disappointed.


Step 2: Make a trello board

If you’re not already familiar with trello, go ahead and either create an account or connect via your gmail. Create a new board. If you need some help with the basics, check out trello’s how-to materials.

Set up your trello board with 3 sections: goals, backlog, and tracked work.

Here’s my board:

Far left: Vision & Goals

Put your vision statement and your 30–60–90 day goals on the far left hand side. This way, no matter what else you’re doing on the board, they will always be front and center.

This a passive way to remind yourself of what you’re striving for. Seeing your bigger picture goals helps you stay on track or realize where you need to readjust.

Simply having them in sight as you look at your individual task will also make prioritizing easier.

Middle: Unstructured to-do list or “backlog”

Next, create a “backlog,” or an unstructured to-do list. It’s important to have a place to dump things you need to do / want to do without that interfering with what you’ve already planned for the week.

Without a dumping ground, it’s easy for urgent, quick tasks to dominate your time. You can easily lose track of little things that you’d like to complete at some point down the road too. Keep yourself on focused and maintain a place to jot project ideas. That place is your backlog.

You can also treat your backlog in a more structured way by listing out all the work that needs to happen for your 30- 60- and 90-day goals. I wouldn’t suggest trying to plan out every task that needs to be done, but there are people who disagree with me. I think if you’re learning anything new or using your time to build something, it’s hard to have a really clear sense of EVERY activity you need to complete, so I would list out what you know you need to do, given your larger vision.

If you want to take this second, more structured approach, I would read up on some of the scrum guidance on creating a product backlog, which is similar to what I’m describing here.

Right: To do, in process, completed

Your holy grail of productivity lies here. Create 3 lists, one called “to do (this week),” the second “in process (this week),” the third called “completed (this week).”

At the start of each week, pull in cards from your backlog to your to-do list or create additional cards for activities you want to complete to reach your goal. To guide prioritizing your work, ask yourself: “What do I absolutely need to get done this week to reach my 30-day goal?”

Plan one week at a time so you don’t get in the habit of working weekends or let big projects slide from one week into the next. Chunk up the bigger projects so they are manageable.

This is important, so don’t just put “apply for jobs” and call it good. Be specific, be time based. Doing so will help you see progress, which will motivate you. Putting items on your to-do list for a specific week will help you actually complete the task because you know it’s related to your larger goal. Holding yourself accountable is key.

Be diligent about updating your trello board too. At minimum update it at the start of and the end of the week. The board wants you to succeed. Use it right so it can help.

At the end of the week relabel the completed with the date of the week, so overtime you build out completed work moving to the right on the board.


Step 3: Treat calendar your calendar like a journal

A key to getting through your to do list is scheduling WHEN you do those specific activities.

I’ll take you through one way to set up your calendar for success. Before I go through it, ask yourself:

  • What are the activities that I do that connect to my larger goals?
  • What time of day works best for me to do certain kinds of activities?

For example, I’m a morning person, so I frontload challenging things, getting them done in the morning. I schedule my activities to optimize energy that I know only have in the morning.

Here’s an example of my calendar for 1 week (note, I’m using google calendar).

This calendar has 4 main characteristics:

  • More is more — Everything is on there. I put running and yoga on my calendar, or even writing in my journal since those are activities that help me build my yoga teaching skills. They are important, and putting them on the calendar means I’m giving myself “credit” for them.
  • Length matters — Err on the side of shorter chunks of time for a specific activity. You want enough time to dig into it, but not so long you get exhausted. I’ve heard that 25 minutes is a good amount of focus time, Cal Newport says 90 minute chunks optimize your mental “flow.” Avoid exhausting yourself on one thing before moving on to the next.
  • Use color — Color code your calendar, so at a glance you can see how much time you’re spending on each thing. At the end of each week, you can easily see how you actually spent your time. This allows you to a) refine your goals if you don’t spend time on it a specific activity and b) realize where you need to change your planning for the next week.
  • Plan to plan — Set aside time to work on the calendar itself. Do it every day. You probably need 15–30 minutes to work on this. You can do it while working on your trello board, but just like everything else, if you don’t put time on the calendar to do it, it won’t happen.

Why be so meticulous about it? Because it’s like a workout buddy. When you put something on the calendar, it’s harder to say, nah, today it’s fine if I start a bit late.

It doesn’t mean you can’t start late sometimes, because life still happens, but do track it. Update your calendar to show when you started working on xyz. The calendar forces you to be honest with yourself so you can put in the work to achieve what you want.

Your calendar will hold you accountable. It’s an asset. It’s your measurement tool, your method for really optimizing the day-to-day of your life.


Step 4: Take good care of yourself

Being your own boss is hard. Sticking to what I outlined above is not easy, and to do it, you need things that give you positive feedback or inspiration to keep moving.

Keep written proof of your awesomeness visible and accessible

Self-doubt is a monster that haunts all of us. Anyone who says it doesn’t is either lying or lacking social awareness. We all feel sad and battle internal voices of hatred, negativity, etc. You know what I’m talking about.

And the hard thing too is it hits at bad times, or when we least expect it. Sometimes it sneaks up and talks down whatever hope we felt before, without us even realizing it.

Plan for those moments. They will happen. It’s no judgement on you, it’s just part of life.

These things help:

  • Put up stickies or written reminders on your computer, bathroom mirror, fridge or workspace. Quotes are good, phrases that resonate, or awards you won help too.
  • Create a google folder/ doc where you store screenshots of nice text messages or emails people have sent you, or copy the text in there directly. Name it “read this when you feel sad.”
  • Send your friends and family letters telling them how amazing they are. They will likely reciprocate in some form. Add these items to your collection.

This is not self-indulgent. This is not selfish. You will only give your best work when you feel good. You bring your unique value in its ripest form when you believe you belong.

But also, do the work when you don’t feel ok. Push through it and stick to your schedule. There’s a beauty in doing the hard things when we feel sad. Sometimes it results in a deeper form of happiness.

Take the time to figure out what you need when and document it.

Have social time

I find people fall into one of 2 camps when working at home 1) they socialize all the time and hardly get anything done or 2) they isolate themselves. You probably already know where you land.

Here’s a benchmark to customize based on what you need.

  • 1 personal and 1 professional encounter per day. Talk on the phone or have 1 face-2-face encounter with someone or a group of people you know personally (ie., coffee with 2 friends). Repeat the same for someone in your professional network. Hearing a voice is important. This is not the same as sending/ reading emails or texting.
  • Limit texting and emails to specific time frames. Maybe it’s once an hour for you, given your work, maybe it’s only a few times a day, but limit it. Otherwise it’s easy to spend all day texting people, hanging out on social media, or reading through emails you really don’t need to read. Use your calendar to help with this.

Reward yourself

Working on your own without structure is hard, but you can do it. You have an internal drive, that when well activated, pushes you to the next thing. We all have it, for some it’s more developed than others, but it’s never easy for anyone.

Like the creep of self-doubt, recognize your drive by rewarding it.

Maybe it’s seeing a movie at the end of week or leaving town on the weekend. Maybe it’s some food you love. Whatever it is, build it into your calendar, build it into your plan and allow yourself to fully indulge. You earned it.