Professional Pivot: Reflecting on My First Quarter in Freelancing 🔄

Reflecting on my transition to freelance consulting, including my role as a fractional CTO and VP of Engineering, what I've learned, and how I plan to engage with clients effectively.

Professional Pivot: Reflecting on My First Quarter in Freelancing 🔄

Issue No. 26

This is a project by Jeremy Brown. I'm a journeyman sharing insights on leading product & engineering teams, building products, and exploring technology.
I will also share occasional updates on my overall project as I build this newsletter (with plans for a podcast and YouTube channel) in the open.

It's been a while! Almost a month without an issue!

Time has flown since the last issue. I took some time off after my first freelance engagement (more on this in a bit), and I've been working on other projects.

I must confess I've also been struggling to be productive.

This week's issue touches on all these topics as I reflect on my first quarter as an independent freelancer.

💬 In this issue, I cover:

  • 🤔 Insights from My Freelance Journey: A Personal Reflection
  • 🚀 Modes of Engagement for Optimal Client Outcomes
    • 🎯 Project or Point-Based Deliverables: Delivering Specific Outcomes
    • 🔧 Enabling Mode: Empowering Clients to Deliver Outcomes
    • 🕰️ Fractional Leadership: Delivering Long-Term Organisational Outcomes
    • 🔍 Engagement Modes Recap: Finding the Best Fit
  • 🏢 What About a Return to Full-Time Employment?

🤔 Insights from My Freelance Journey: A Personal Reflection

I just wrapped up my first freelance role as a fractional VP of Engineering for a startup based in France. It was an interesting and successful experience. I find it hard to look back at these things because I can focus on the things that could have been done differently rather than on the big picture of a successful engagement. The reality is that my client and I are pleased with the progress we have made in a short period.

I'm now looking forward to my next missions and the challenges and learnings to come.

I have to admit that being independent has been a refreshing change for me at this stage of my career, but it hasn't been all roses either.

To share some of my feelings with you, dear reader, I've tried to capture the pros and cons (and my feelings) as I settle into this new world of being a free agent.

Things I love about being a freelancer:

  • I have a much more flexible schedule. I've been able to set my hours and work at times that suit me best. This also includes being able to work on other projects outside of work, from hacking around with my homelab to trying to get stuff done around the house. This lack of structure from a job can take time to adjust - see the section on challenges below.
  • Furthermore, it's been brilliant to say yes to friends who can come and visit, knowing I can easily adjust my schedule and take time out when they are around.
  • Working with multiple clients and talking to more organisations means I can learn from the many different environments my clients operate in, see patterns and discover what works generically across various industries and organisations.
  • Being a contractor has allowed me to maintain a clearer separation and detachment from the job and the organisation, which has benefited both me and my clients. I hesitate to write this as I worry my clients might misunderstand what I'm trying to express. I'm less emotionally involved in my job now. Let me explain. I'm the type of person who commits fully to whatever I'm doing. In past roles, this often led to overcommitting myself to my role, team, and the organisation, tying my self-worth and happiness too closely to the organisation's success. This wasn't always healthy, and I see now that it led to burnout, or near burnout, in several of my previous jobs - not good for me or my former employers!

Some of the challenges of being a freelancer:

  • My income is unstable, and I don't have the same job security as before. As the primary breadwinner in the family, I feel a fair amount of pressure to make sure ends meet. While savings and unemployment benefits in France give me a pretty decent runway, it hurts to eat into hard-earned savings that could go towards things like my son's future education and our retirement.
    Indeed, as a contractor, you bill at a much higher rate, but this is without employer-provided benefits. Instead, you carry a lot of extra costs you don't have as an employee, such as accountants, business banking and insurance, on top of providing benefits like healthcare for yourself. At the moment, I'm still in the booting-up phase. I'm giving myself time to figure out a few revenue streams beyond contracting. However, contracting is my only source of revenue at the moment.
  • Most contractors, myself included, are not billing for 100% of their time in long-term engagements. This means I always need to keep an eye out for what I will do next and be "out there" networking and marketing myself by posting on LinkedIn to promote myself and drum up awareness and leads for my next role!
    • While I do enjoy writing this newsletter, and I get a lot out of it, I have to admit that I still haven't figured out a way to promote it and myself on LinkedIn without getting sucked into a vortex of engaging on social media or having to keep up with how the algorithm works and crafting what I have to say into a format that gets attention while not making me feel like I want to vomit when I read it afterwards (think crappy clickbaity headlines etc). I will try a different approach in the coming quarter than the one I've been trying (alternating between trying to post a few times a week and avoiding LinkedIn altogether!).
  • Client Dependence: A significant part of freelancing involves maintaining strong relationships with clients, as their satisfaction is crucial. This dependency can sometimes be stressful, as you must balance being honest with the client about their situation even as you depend on them for your income. I'm working hard not to put all my eggs in the same basket and to build a "balanced portfolio" of work.
  • Being a freelancer can leave you feeling more isolated and having less contact with others. One of the things I miss about full-time employment is the daily contact and exchanges with my colleagues. I really miss the communal lunches, chats over coffee or going for a walk around the block during a 1:1. In every job, I've made some great friends, but when you don't work with folks anymore (and in my case, when you move across the country), it is much harder to stay in touch. It's hard to have such an abrupt drop-off in seeing folks you made friends with. I've been fortunate that my work has allowed me to be back in Paris fairly often this past quarter, and I've made the most of that by trying to catch up with folks when I'm in town.
    Now that I recognise this, I'm also trying to compensate for this in other ways, for example, having standing calls with folks.
    I hope that some of the collaborations I'm working on will allow me to work permanently with some of the great folks I've met through work.
  • This has been a big one for me. Motivating yourself to get stuff done can be more challenging, especially without the structure of a traditional job. It has taken a bit to adjust to having a less structured schedule.
    I've dived down some super deep procrastination rabbit holes (mostly to do with my homelab setup).
    After going straight from my previous job to a fractional role, I think I also needed some "downtime" over the last month.
    Still, as I write this week's newsletter after a small hiatus, I sense I'm ready to start throwing myself back into a few projects.

Those first two items of not having income stability and needing to find my next gig come with huge pressure! Some of it comes from needing to promote myself online. Still, the other part of the pressure comes from the unpredictable income of a freelancer alongside the predictable costs of a mortgage and bills.

🚀 Modes of Engagement for Optimal Client Outcomes

Now that I have completed my first contract, I can better articulate how I help folks.

Based on the work I've done so far, I've identified the following modes of engagement that enable me and my clients to have the best outcomes when working together:

  • Project or point-based deliverables - delivering specific outcomes for the client.
  • Enabling mode with a sliding scale of involvement - empowering clients to deliver outcomes.
  • a Fractional (part-time) role as a CTO or VP of Engineering - delivering long-term outcomes inside a client's organisation.

 🎯 Project or Point-Based Deliverables: Delivering Specific Outcomes for the Client

This first type of engagement is where the client has a specific deliverable that needs to be done, such as an audit report or facilitating a workshop or event. 

This should be a loosely coupled deliverable with clear interfaces around what the client provides and what I need to deliver. In this mode, things get complicated when we introduce too many dependencies or the project needs to be more tightly coupled.

The result will be within my control as long as the client provides their side of the deliverable.

In this way, the client and I are set up for joint success for the deliverable.

✅ Examples of Projects I Can Do

It might help for me to provide an example of the types of things I could do using this mode of engagement:

  • Facilitate a team or department offsite using Open Spaces: I'm used to facilitating large-scale workshops of up to several hundred people. This is one of the most unique and engaging ways for an organisation to run an offsite.
  • Facilitate a multi-day product and engineering planning offsite: this is a more structured workshop that brings together product and engineering to retrospect on the past quarter and to prioritise and plan the quarter ahead.
  • Carry out a technology audit and make recommendations: Conduct a comprehensive review of a client's current technology stack, architecture, and processes, and provide detailed recommendations for improvements or new technologies to adopt.
  • Strategic roadmap development: Help the client develop a long-term strategy that aligns with their business goals, including timelines, key milestones (or increments), and required resources.
  • A security assessment and enhancement plan: Evaluate a client's cybersecurity measures, identify vulnerabilities, and create a security enhancement plan to protect against potential threats.
    This is an area I can help with as I've been the CTO of businesses of various sizes and have had to contend with the security requirements of Enterprise customers (such as SLAs and security audits written into contracts).
    I've also successfully run a company with the more stringent SOC 1 Type 2 certification.
  • Software Development Lifecycle (SDLC) improvement: Carry out a Value Stream Mapping (VSM) exercise or use Metrics-based Process Mapping (MBPM) to review a client's SDLC processes to increase flow, improve quality, and reduce time-to-market for new software releases.

🔧 Enabling Mode: Empowering Clients to Deliver Outcomes

The second engagement mode is to act as an enabler, working alongside a client who is seeking to level up themselves and their organisation.

I've built extensive experience as a stabilisation, turnaround and growth CTO, working to deliver outcomes for the business while working with my team to enable fast flow by using open leadership and working small. Almost all of my experiences have had an element of shaping a business for the future while often working in a severely resource-constrained environment (I've had to downsize my team twice).

With the end of "free money," many Product and Engineering leaders encounter similar scenarios, often for the first time. Having a copilot, not just as an advisor and mentor but also as someone who spends a significant amount of time directly involved in the organisation alongside the leader, will significantly de-risk and accelerate their progress.

My operating mode would heavily use the same interaction patterns as pair and mob programming, as well as one-to-one coaching and mentoring:

  • Coaching and mentoring sessions one-to-one.
  • Building through pair programming, either with my "hands on the keyboard" (so to speak) and the client overlooking, or vice versa, alternating between us to "co-build" something.
  • Learning and knowledge transfer through mobbing as a group, with either myself or someone else driving, fostering collective learning on technical and non-technical topics.
  • Asynchronous research and sharing of options, examples, or documentation to accelerate the client's learning.

The key thing in this mode is that the client would enact change rather than myself.

🛠️ Examples of What We Can Do With Me in Enabling Mode

  • Enhancing team performance and processes: Implement processes and practices that enhance team productivity and communication, such as introducing agile methodologies or improving existing workflows.
  • Crisis management and technical debt resolution: Identify critical technical issues that are impeding business progress and lead the charge in resolving these while also strategising on reducing technical debt.
  • Scaling architecture for growth: Assist in evaluating and redesigning the system architecture to handle increased load and complexity as the company scales.
  • Preparation for funding rounds or an acquisition: Help prepare the technology aspect of the business for upcoming funding rounds, ensuring that the technology strategy aligns with business goals and investor expectations.
  • Strategic projects and initiatives: Provide leadership and oversight for specific strategic projects where the existing team needs more bandwidth or expertise. This could involve spearheading new technology implementations, leading digital transformation efforts, or managing the integration of newly acquired companies.
  • Mentorship and team development: I mentor senior technical staff, helping them develop their leadership skills and preparing them to take on more significant roles within the organisation. This can be crucial for companies looking to cultivate their next generation of technical leadership from within.

🕰️ Fractional Leadership: Delivering Long-Term Outcomes Inside a Client's Organisation

The final approach is more where I'm in the driving seat, taking on a role in an organisation in a fractional or full-time capacity. The key criteria for considering one of these opportunities is that it needs to be a medium to long-term gig so that I can make a difference during my tenure, so this is a minimum of 3-4 months and ideally longer. Six months or more to have a significant impact.

Since this involves managing people, getting up to speed, and making necessary changes, interventions, or stabilisations, it can be intensive at the outset, often requiring three to four days a week in the initial weeks. As things stabilise, this might transition to a part-time engagement of around two to three days a week.

In this role, I would have full authority, whether as a fractional CTO or VP of Engineering, focusing on delivery and longer-term responsibilities like managing people, making strategic decisions, and implementing them effectively.

🌟 Where I Can Help as a Fractional Leader

For companies, using a fractional or interim CTO gives them access to cost-effective, flexible, and specialised technical leadership that can be tailored to their specific needs and stage of growth.

I can see my services being particularly useful in the following scenarios:

  • Interim Leadership During Recruitment: I can step in as an interim CTO or VP of Engineering to fill a temporary gap in leadership, such as during a transition period when the permanent leader is being recruited or when the current leader departs. This ensures continuity and stability. 
  • Fractional (part-time) leadership is ideal for organisations that need an experienced leader but can only afford a part-time position. This arrangement is a cost-effective and smart investment for many smaller organisations preparing to scale and expand. Having myself work 2-4 days a week alongside their team for an extended period can help avoid many common pitfalls and challenges that product and tech teams face as they grow. Additionally, I can provide an experienced product and tech voice on the company's executive committee.

As a fractional or interim CTO, I can provide high-level technical expertise and leadership without the full cost (and commitment) of a permanent, full-time CTO, making myself ideal for startups, small-to-medium businesses, and companies that don't require a full-time CTO.

I can bring a wealth of experience and technical knowledge through myself and my network that can be leveraged on-demand, which is especially beneficial for companies that need more in-house technical leadership or are facing complex technology challenges.

Furthermore, I can help align a company's technology strategy with its business goals, providing high-level strategic direction and oversight. I can see how valuable this would be for companies undergoing significant transitions or seeking to leverage technology for growth.

The advantage for companies is the flexibility to scale up and down my involvement as needed, whether for a specific project, a transitional period, or ongoing strategic guidance.

🔍 Engagement Modes Recap: Finding the Best Fit

I made the following table to summarise these different engagement modes for me and my clients.

Characteristic Project-Based Mode Enabling Mode Fractional Mode
Outcome Deliverable-based Knowledge transfer while derisking and accelerating the client's initiatives Strategic and operational impact
Scope of Work Well-defined, narrow-scope Broader scope, flexible Broadest scope, strategic
Duration Short-term Medium-term Long-term
Type of Involvement Specific task-focused Advisory, coaching Deep operational involvement
Coupling Loosely coupled Moderately coupled Tightly coupled
Interaction between client and myself Transactional Interactive, educational Integrated, managerial
Client Flexibility High (task-specific) High (can end the contract at any time) Medium (can flex my time, but it's usually a longer-term commitment)
My Dependency on the Client Minimal Moderate High
My Flexibility High (task-specific) Medium (time-boxed) Low (role-specific)
My Income Predictability Variable Reasonably predictable More stable

As I write on my About page:

I'm passionate about helping people thrive 🌱

My mission is to cultivate environments that unlock the potential of people in teams to achieve remarkable outcomes for them and their organisations.

Looking through this lens, I prefer to work with multiple clients in enabling mode with the occasional longer-term fractional or embedded role. That would give me the best mix of flexibility and income stability while also allowing me to help more organisations simultaneously. 

🏢 What About a Return to Full-Time Employment?

Returning to a full-time role is appealing, though I would approach this option thoughtfully to ensure the fit is right. I love building a product and an organisation for the long term alongside a bunch of great people, and that is an environment in which I thrive.

Thankfully, it's not something I have to rush into, so I'm not trying to grab the first role that comes along.

Since I'm keeping myself open to this option, I feel a lot of pressure to make the most of the time and freedom I have to get some of the projects I have on my list up and running (watch this space for more on that!).

So that's what I've learnt so far!

💬 If you had some thoughts while reading this, I would love to hear them in the comments.

🔦 Highlight of the Week

I've written about how I disagree with performance ratings and recently came across this quote about them from THE master, W. Edwards Deming, in a really good article by Phil Haack called Abolish Performance Reviews.

If you have doubts about performance ratings and performance reviews, it's worth reading the full article.