Tom Jepson Creative

Looking Back - A Company of One Retrospective


(If this article has TL;DR all over it but do want to run a retrospective for yourself, jump to the bottom of the article for an outline of the workshop activity. Still, I'd appreciate it if you read the whole thing...!)


Taking stock of what we do as individuals running a business is paramount to us making progress and setting ourselves up for future success. As a company-of-one, it can be extremely easy to let the world pass by, moving from project to project, without really noticing where you started and where you’ve been.

"Have the things I’ve done moved the needle against the things I set out to do?"

The challenge of ‘having to do it all’ can leave us a little blindsided; we get to a point where we’ve blinked and missed it! We’ve come to the end of 2019 - a year and a decade. There is no better time to look back over what we have achieved and start to consider ‘What next?’.

The Three Questions

  • Where did I begin?
  • What have I done?
  • What did I learn and will I do with it?

Where did I begin?

Before we begin the deep introspection, take some time to shout about your headline news. These are the critical points where you really felt like you were on top of your game and where you came up against adversity (which you’ve obviously overcome else you wouldn’t be here right now).

What were your highlights? What were your biggest hurdles? I like to think about three of each before I go any further. These highlights and hurdles make up our defining moments.

Entering our retrospective, we should look to our starting point. The place and context in which we begin can hold a lot of sway over how we conduct our journey, be it driven by our own motivation or an outside influence. Give yourself time to think about what you had, what you set out to do, and why you set out to do it. Only then will you be able to measure against reality and know how far you’ve come.

Ask yourself:

  • What did I have in hand when I began my journey?
  • What goals did I set for myself or my business? Why?
  • Was my journey based in strategy or was I looking at moving only tactically?
  • Was I continuing something I’d previously explored?

What have I done?

Even if you don’t feel like it, you’re going to have made some progress; let’s celebrate that fact by looking at all of the work you’ve undertaken and milestones you’ve hit.

Maybe you’ve just started out and are still in an unknown land; that’s OK. Take a look at the little steps you’ve made.

Maybe you’ve been working with the same client for the last 6 months, grinding the same ol’ thing week in week out. What can you say you’ve put your hand to in that time?

The facts you gather here - the clients you’ve worked with, the projects you’ve completed, the invoices you’ve had paid - are only one measure of your success.

Think about how far you have come personally. What achievements do you feel like you’ve made for yourself? If you’re working for yourself or are selling a service that is based around your skills, separating yourself from the work is likely a challenge. Your personal growth will be integral to the progress of the business.

Record everything you can think of - big or small - to paint a picture of the journey you’ve taken. Once you’ve got this picture together, it’s time to compare and contrast against your starting point.


Sidebar: A daily progress diary

Something which I started to do over 200 days ago was recording my actions; all the activities I did each day while I’m working, coupled with a little statement about why I did it. I use Notion - my go-to tool for keeping my business in check - as my diary.

Doing this - and taking the time to look back - has kept me motivated throughout the year, and has shown me when I need to go ‘up a gear’ and push just a little harder.

Why not try doing this for yourself in the coming year?


What did I learn and will I do with it?

It’s time to get serious. You’ve taken the time to travel back to the beginning of your journey and retread the miles, marking the milestones as you go. But what are you to do with this?

The first question to ask is "Have the things I’ve done moved the needle against the things I set out to do?". Basically, did I succeed against my goals? Depending on how you’re viewing your starting point, you might have some objective and subjective readings to take.

You might think this is quite a tough line to take, but I’d argue that a little pragmatism is healthy and should certainly not be used as a stick with which to beat yourself. You - and I - need to understand if the things we’ve done have been effective in pushing us forward professionally and personally. We also need to look at how sensible our planning was at the outset!

Over-committing - setting over-optimistic goals - at the beginning of any period or project is common. Even if we’ve got prior learnings on which to base our goals it’s really easy to get swept up in taking moonshots.

So how did you answer? If you don’t feel like you’ve ‘achieved’ don’t beat yourself up, and maybe take another look. I’d argue (again) that there will have been something that took you even one step forward.

Don’t worry about it whatever you do. The next step is what is really important.

What did you learn?

The things you take away from your actions - both successes and failures - are what will determine how effective your next steps are. If you can find patterns in your successes, what can you do to refine and leverage that? If you spotted some missteps (hopefully not repeated too frequently), what can you do to make sure you don’t trip over again in the future? These learnings will help you in your planning and will give you some steer to start on the next part of your journey. Remember, however, that all planning should be flexible; planning is great, plans are not.

Whatever position you have reached, you have my utmost respect. Working as a company of one in whatever field you are in is hard; very, very hard. It might not feel it day to day but keeping that momentum going and really keeping on track to reach the goals you want to reach can take acts of Herculean strength.

You’ve proven you can do it, and I have, too. Be proud to say so! Take the things you’ve learned and set out as your ‘big actions’ and step into the New Year with enthusiasm.

You’ve got this.


Let's Get Practical - Running Your Own Retrospective

You can record your retrospective in a really easy way. I like to use MURAL for these big activities because it saves on Post-It waste and it means I can look back and review as and when I need to! Pen and paper are, however, just as good if you want to get away from the screen.

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NB. If you don't want to do the affinity mapping, walk through steps 1-3 and then skip straight to step 7. You can find out more about affinity mapping in this article.

  1. Before you begin, ready yourself. Why not start by recording three things which you deem to be your greatest successes or achievements in the last year. After that, think about the three things which you deemed to be your biggest blocker. These are your defining moments.
  2. Now, go back to your beginning and list out your starting goals and what you had in hand.
  3. Next, list out all the things you’ve done; projects complete, courses you've taken, skills learned, conversations had...
  4. Now it’s time to affinity map all the great insights you've gathered. To do this, you'll want to group the activities you've against the starting points you wrote down; you’ll likely be able to match the activities to more than one goal (This is where doing the retrospective digitally can really help)
  5. Look at each of these groups and give yourself a rating from 1 to 5 - 5 being ‘Absolutely smashed it’ and 1 being ‘Something didn’t work here’. This activity is a giant shade of grey so categorical Yes/No answers aren’t really helpful.
  6. The most important step is this: what did you learn? For each group, or task, or goal, or [thing], write down what you learned, what you observed, what mistakes you made, what you definitely want to take forward. There might be a lot of things, there might only be a few; it doesn’t matter as long as you take the time to be introspective and get it down on paper.
  7. Big actions. Looking over the learnings you’ve written down, find three which you feel are the biggest takeaways that will help you in the coming year (or maybe just the next quarter). It might seem like overkill, but I like the traditional Eisenhower Matrix; the impact/effort grid. Plotting learnings here helps give a clear picture of the things you believe are going to be most helpful to you.

Wrapping Up

The only person who’ll be using all of this material is you, so try and be honest with yourself. You can find the MURAL template I've created for the Company-of-One Retrospective here. If you want to read the article which inspired my solo retrospective and want to learn how to run a retro for a remote team, you can find it here.

Let me know how you get on running your own retrospective. Did you find it useful? If you would like help setting up for success in your future project, let's talk!