The Accomplished Solopreneur

Issue 23.36

Saturday, September 9, 2023

Annual Retrospective - a Guide for Solopreneurs

Yesterday was my birthday (thank you, thank you!), and because it’s “my” day I took some time out to think about the year that was, but more importantly, what’s ahead.

I’m not going to bore you with the details of my musings, but I would like to give you some guidelines on how you can do your own.

Every time I do this, I walk away with my head held high and a spring in my step. Highly recommended.

The outline

Being the self-diagnosed geek that I am, I tend to put structure into just about everything. In this case, I keep it really simple:

  • The year that was
  • What’s cooking
  • Gratitude

And then there are some lessons I’ve learnt from doing this over a number of years.

Part 1: The year that was

The ups and downs of every day tend to blur what we really achieved in the last year. In this part I try think about where I was a year ago, and compare that to where I am today.

Taking this longer-term view highlights just how far we’ve come.

The key for me is to write it down - I tend to use pen and paper because I don’t want to get distracted by computer beeps. I also find the more I write down, the more I discover that’s worth remembering.

I tend not to dwell too much on negative things – except if they were really major. Those are worth writing down, because it helps us remember those things are in the past, and we can let them go.

Sometimes I will even scroll back through my calendar to see what happened each month. This is sometimes a reminder of good things I’d forgotten about.

At the end of this part…

I usually feel pretty good because there was an unexpectedly large number of good things. In my own past, some years sucked – but the majority have been great. In retrospect.

Part 2: What’s cooking

This part is really about looking forward - and how “what’s cooking” will help me get there.

In the past, I experimented with goal-setting (just about every system known to man and a couple that haven’t been invented yet). Most of those systems turned out to be more hassle than they’re worth, and missing goals or deadlines turned out to be more of a downer than motivating.

So now, as a solopreneur, looking forward is simple:

  • What’s the next big milestone in my life?
  • What have I got cooking right now to help me get there?
  • What are the next 2-3 things I need to make that happen?

There’s one major change from how I used to do this in the past:

I focus on the next big milestone in my life – not my business.

Seriously folks, life is for living, and work or business is becoming more of a means to an end rather than an end in itself. I went through a phase when work was life – but I got too deep into that rabbit hole and paid a price. Fundamentally, I don’t want to look back and regret things I didn’t do.

Your priorities may differ and that’s fine. If you do spend all your time working on and in your business, I invite you to think about what you’re missing. You may be fine where you are – in that case, great. If not, adjust.

At the end of this part…

I’ve refreshed my view of what I’m doing, and why, and what I need to do over the next 2-3 months. The road ahead is clear.

Part 3: Gratitude

This is probably the most energizing part of the whole exercise.

I’m really, really fortunate to have many things to be grateful for. First is my loving and incredibly supporting wife – thank you mi amor. Then there’s health, home and family – even Diego the Dawg who’s always irrationally ecstatic to see me.

These things are worth writing down. And write down everything you can think of, even if you think it is small. Most of you reading this will be living in a good part of the world, and we have a lot to be grateful for.

I have a long list, including everyone who reads, comments and gets some value from these newsletters. Every time I hear from you, you make my day.

At the end of this part...

I'm incredibly happy for all the good things in my life.

Lessons I’ve learnt

The longer I’ve done this, the simpler it’s gotten.

I used to have major systems and methodologies for planning my life in incredible detail. Some of those things are still useful, but this last exercise was just me, a coffee, and pen and paper.

Even my planning has simplified. I’ve learnt large-scale project management from some of the best, and in the past that crept into almost everything I did.

Complexity has given way to clarity. The simpler things are, they easier they are to deal with.

So there it is. Thanks for sticking around. SoloBOSS is coming, and I’m really excited. (That’s “what’s cooking” for the next big milestone in my life.)