90 Days In: Key Lessons from My Solopreneur Journey

Discover the insights gained from the first 90 days of solopreneurship, covering the balance of efficiency and focus, personal versus professional time, the art of saying no, and more.

I switched my career from full-time employment to solopreneurship at the beginning of 2024.

In today's article, I'm going to share with you some of the key observations and lessons after my first 90 days of operating as a Solopreneur. And I'll share how these lessons have influenced the way forward for my business setup.

📆 Lesson #1: Attention fragmentation creeps up on you

At the beginning of the year, I spent a reasonable amount of time setting up my cal.com structure and integration with my 2 main Google calendars: Personal and Professional.

Once I validated that the setup was solid, I started sharing scheduling links with prospective and actual clients to streamline the process of booking meetings.

✅ That was very time efficient: I rarely had to go through the tedious yet very common process of back-and-forth messages with someone just to find an available slot.

This approach though started to show some leaks once the amount of individuals and clients I was working with became more significant.

As I was mainly optimizing the booking process for efficiency, anybody could book a meeting within any available slot, regardless of what came before or after it. They wouldn't know as nobody has full visibility on my calendar. And even if they did, why would they even care?

❌ The Downside? Attention Fragmentation. I'd be jumping from a call with Client A to another meeting with Client B, then maybe a 1/2 hour to work on stuff, and finally a session with Client C.

Once this became evident, I realized that the desire to accommodate client needs and be efficient with their scheduling needs was getting in the way of me doing a good job.

I was forcing myself through a lot of context switches, which ultimately affected my efficiency and the quality of my work.

In other words, my focus on improving the efficiency of the booking process led to a reduction in the efficiency of my work. A good lesson on narrow optimization as opposed to system thinking. 😊

I've now restructured my scheduling and booking links so that my week is organized around chunks of 1/2 days:

The default structure of my calendar now

Additional work such as admin tasks, etc will take place during the blocks that are open for Coaching sessions or Discovery calls that have not been booked.

I've used a very similar chunking approach in previous roles as well and it helped me drive focus and go deep on specific areas, one at a time.

I've just deployed this into my new schedule last week, and I'm already seeing good improvements in focus and depth.

⏰ Lesson #2: Time Boundaries between Personal and Professional will blur

We're all way too familiar with the tendency of work to expand and occupy part of our leisure or personal time. That typically leads us to have to sacrifice parts of our lifestyle to accommodate the growing demands of our jobs.

Though there is always a personal choice at the origin of it, the pressure that comes from our environment might leave us with the impression that we have no choice.

One of the key reasons to start this new journey was to flip the system on its head and start designing my work obligations and commitments around the lifestyle I wanted to live.

Besides when I'm in meetings with clients, how I structure my time is entirely up to me.

Even though I always benefitted from a good degree of autonomy in my previous jobs, they all involved some expectations - oftentimes self-imposed - to be available and online when most of the other people in the org would be.

Today I don't have a company Slack I need to constantly monitor, and that has been a massive improvement in my ability to be flexible on how I invest my time.

I still occasionally cringe at the idea of taking time off during the day due to decades of mental conditioning on the 9-to-5 workday, but I'm gradually becoming more comfortable with it.

I look forward to Monday mornings because I start the weekday mornings by cycling to a Dojo, where I spend a couple of hours practicing martial arts and then cycle back. At first, doing this while everybody else was at work felt like cheating, but it has become my new regular.

Starting the week with exercise and a slow pace instead of frantically going through my work obligations has proven to be a massive improvement in how I live each week.

Another example of letting my personal life reclaim space includes taking long walks in the middle of the day, some of them used as forms of Productive Meditation.

I've planned to take one just as soon as I'm done writing this newsletter.

And since I mentioned it, is this newsletter a professional or a personal endeavor?

It is both.

That makes sense in a reality where my craft is something that requires discipline and is supposed to generate financial outcomes on the one side, while also providing an opportunity for growth and learning that positively contribute to a better quality of life overall.

The blurring of boundaries is not without its challenges, as the pressure of financial goals and needs could push me in the opposite direction.

By reclaiming time for personal growth I'm most certainly leaving some money on the table, and that's a conscious prioritization decision.

To make this possible I need to practice another skill, and that's saying no.

👎 Lesson #3: Saying No is even more important (and harder)

It is difficult to say no in traditional work environments. When you're your own boss, that's one order of magnitude harder.

While as an employee saying no might get you in trouble with your boss, doing it as a solopreneur might have some serious financial consequences.

The absence of a fixed salary at the end of each month can become a serious limitation to your ability to decline a new engagement or project. It's way too easy to let you be driven by the inherent uncertainty about future revenues and just say yes to anything that is being thrown your way. Just in case you might end up with zero clients in a few months.

I must confess that my first reaction to every request for a new engagement is biased towards accepting it exactly for those reasons.

What if I say no and I regret it?

What if I say no and next month I lose one of my clients?

What if someone else launches a product similar to something I have in mind before I do?

I've let myself be driven by those fear-generating questions more than once during the first 90 days, and I'm pretty sure I will again in the future.

However, I have become more aware of it and have been successfully pushing back on a few important occasions.

I've learned that being confident in your ability to build something sustainable from what you're already doing can increase your ability to say no.

Instead of trying to do more things to hedge your bets, focus on getting better at what you're already doing.

When you start something new it's very difficult to say no as you have little to no evidence that what you're doing will yield good results.

There is a risk of cornering yourself in this mental space indefinitely as the future is always uncertain. There are so many external factors that could impact your success.

Here is where the foundational lessons from Steven Covey on focusing on your Circle of Influence rather than your Circle of Concern became useful.

The best way to increase your ability to say no to any new request is to not need it.

The best way to not need it is to have a pool of clients who are very satisfied with you, leading to high retention and low churn.

The best way to achieve that is to do such a good job that they will have no reason to go elsewhere.

As I want to be able to say no more often in the future, I should focus on doing an even better job with my current clients.

That's entirely in my control, and it's reassuring.

⚖️ Lesson #4: Consulting vs Mentoring - AKA B2B vs B2C

I currently offer my services both to companies - B2B clients - and individuals - B2C clients.

I started my journey by offering a relatively broad set of services as a way to learn and figure out what I should double down on, and what to eventually discontinue.

I know I will narrow down my scope at some point, and this first quarter has provided some insights into what I might want to focus on and go deeper with.

The main benefit of offering consulting services to companies - such as Fractional CTO or project-based consulting - is that these tend to be high-ticket clients. The vast majority of my revenues in Q1 came from these types of engagements.

The downsides though are multiple.

First of all, these engagements can end up being just a glorified version of full-time employment.

The more you get involved with such roles, the more their time requirements and mental load tend to expand beyond the boundaries of what you had allocated to them.

Secondly, each one of them tends to carry a significant amount of cognitive load with it.

You need to learn the intricacies of different teams, organizations, projects, systems, architectures, etc. Switching context between different clients can be mentally very taxing - as we've seen in lesson 1.

As a result, you will end up mixing things up or forgetting important details, no matter how good your notes are. This means you can only have a few of them in parallel before the quality of your work starts being negatively affected.

Third, as they are just a few high-ticket clients, losing one has a major impact on your overall revenues, and can seriously disrupt your plans as you try to make up for the revenue loss.

Finally, every company will try to negotiate with you, and every engagement will be tailored to their needs.

This does not only concern the scope of work, but it also involves fees, discounts, payment terms, etc. Chances are you will have different fees structured for each different B2B client.

That doesn't only make it more difficult to prioritize work, especially for lower ticket clients, but it also increases the amount of overhead.

Working with B2B clients is great, but it does come with a load of complications and higher overhead.

Conversely, working with B2C clients is almost the opposite: lower-ticket clients, lower cognitive load, and lower overall impact when you end up losing one client.

I also found that I enjoy a lot more working with individuals, building a long-term relationship, and helping them overcome challenges they're facing.

This isn't surprising if you consider that as an engineering leader, I've invested years practicing and honing my skills in this area.

And that's why in Q2 I'll shift my focus primarily to onboarding new individual clients into my mentoring and coaching services.

The hypothesis to validate is whether I can build up a pool of clients big enough to be a viable business on its own, reducing the dependency on bigger B2B clients.

I guess that will be a lesson to be shared at the end of the current quarter!

Lesson #5: Find people who are willing to criticize your work

Though it's always rewarding to receive praise and compliments for the work we do, these often tend to offer very few insights on how to improve.

Yes, testimonials and recommendations can play a very important role in landing you new engagements, but in that capacity, they're more marketing assets than actionable feedback.

As a Solopreneur you don't have a manager, and you don't have a team. That has its advantages of course, but it also means that you are not surrounded by people whose responsibilities include providing you with timely and recurring feedback.

If you want actionable feedback, you need to find people who are willing and able to constructively criticize your work. And one you find them, make it a habit to ask them for feedback regularly.

As I've been sharing my content more broadly and more proactively in the past few months, I've systematically asked for feedback. I've been fortunate to get the attention of a bunch of people who share their views either on my ideas, the format, or both.

I've learned more from those few uncomfortable interactions than from all the likes, thumbs up, and positive comments accumulated along the way. These are still important, but they are a lagging indicator. They tell you that you're doing something right, but not what exactly.

One single person who is willing to engage with your content critically and constructively is worth more than tens of hundreds of silent followers or readers.

Don't simply acknowledge it.

Build your informal advisory board, and capitalize on the insights you'll collect through it.

🏁 Conclusion

The first 90 days of the Solopreneurship journey have been a blast. I went from the I have no idea what I'm doing stage to having some ideas on how to approach this space that is still very new to me.

As Q1 came to an end recently I wanted to share with you the 5 main lessons I've been learning since the beginning of the year.

I hope these lessons might prove useful to anyone else who is considering a similar move.

As usual, let me know if you find this useful in the comments section.

See you next week!