Why I Quit Google to Work for Myself and What I Learned In My First Year

May 20, 2021

May 28, 2021

Why I left a “dream job” to start my own company and what I learned (and earned) during my first year in business.

Year One: Nobody is going to paint the ceiling but you! (Photo by Henry & Co.)

A few weeks ago, I celebrated my first business birthday! 🥳

It’s been a rollercoaster year and an interesting time to start a new venture to say the least. I’ve been reflecting on what the last year has taught me and wanted to share this thought process more broadly.

In this article, I’ll aim to:

  • Discuss why I quit my job at Google and the thinking behind it
  • Address the money question (“Can I earn a living working for myself?”) that prevents many people from taking the leap
  • Give a full operational and financial breakdown of my past year in business
  • Share a few lessons I’ve learned along the way

This is a longer and more detailed post than my normal musings, so I’d invite you to skim and dive deeper into the parts you find interesting.

It’s mainly a way for me to think out loud, but I also hope it can be useful for someone considering starting their own thing.

Let’s get to it.

Preface: Build In Public

Some of you might be familiar with the “Build in Public” movement that has taken off in recent years, especially amongst online content creators. Essentially, it’s a mindset shift that encourages entrepreneurs to share their work in the public domain. To me, it’s about transparency and celebrating progress rather than perfection.

I’ve learned a ton from folks like Ali Adbaal, Anne-Laure Le Cunff, and Nat Eliason who document their progress so that others may learn from their experience. I see this post as my small contribution to this space; a chance to share openly so that together we can learn from each other.

One important caveat before we go further: I am not sharing financials to impress anybody. It’s not like I made a killing anyway! My motivation is that by sharing openly, someone reading this might learn something valuable they can use on their own journey.

Part 1: Starting a Business

For those who don’t know my work, I run a training company that helps businesses rethink productivity and build resilience for the future of work.

I primarily operate in the Learning and Development (L&D) space and am mainly seen by my clients as a “training provider.”  In that sense, I’d classify the business as a B2B, service-based business, but with dreams to create more scalable products soon.

I currently trade under my own name, Connor Swenson Coaching Ltd.

Here’s a look at the origin story of how I got here.

Finding a Problem Worth Solving

I joined Google straight out of college and spent most of my seven years at the company working on an amazing team called Google for Startups (fka Google for Entrepreneurs).

Despite many years of working to support startups and startup community builders, I did not have a clear roadmap for starting a business when I left. Sure, I had picked up some useful, generic startup knowledge in those years, but actually doing the damn thing is different.

In essence, learning about something and doing that something is an entirely different animal.

It’s the ugly transformation of knowledge into wisdom through experience.

Even if I didn’t feel entirely prepared, I still did take a few valuable nuggets of wisdom away from my experience at Google for Startups. Perhaps the most important was this: creating a business is all about solving a real human problem.

I recognized, through anecdotal lessons and cold hard data that many entrepreneurs fail because they create a cool product or technology without addressing a need in the market.

Top 3 of 20 Reasons Startups Fail, according to CB Insights

As I thought about starting this business, I reflected on my own experience, what I had heard from others, and some general research to draw some important conclusions.

In short, I knew these things were true when I started out:

  1. People are struggling with focus and time management and it's having an impact on well-being, performance, and job satisfaction.
  2. Businesses are willing to invest in solutions for this problem.

Now I must confess, I didn’t conduct any in-depth user research on either of those insights. They were more instinctual and experiential observations I had made.

Coworkers at Google, startups in the communities I was working with, and most of my friends were all incredibly busy, distracted, and stressed. Knowledge work is demanding and it can take a toll. This was a problem I didn’t think was going away anytime soon.

I was thinking a lot about these problems through the lens of my own personal experience, in which I had spent years and years obsessing over how to master my own challenges balancing performance and well-being at work.

It was my own search for solutions, in which I scoured books, attended workshops, interviewed experts, experimented constantly, and consistently tried to learn and adapt for my own sake that led me to different frameworks, practices, and approaches that I found made a difference.

Once I had figured out how to stay (relatively) calm, balanced, focused, and productive in my day-to-day, it wasn’t long before I was able to share these insights and practices with others.

Testing My Approach

Luckily for me, Google gave me a training ground to test whether I could help solve these challenges for others.

For example, while working at Google:

  • I became a certified internal teacher for one of the company’s most popular leadership programs, Search Inside Yourself.
  • I volunteered my time to facilitate gLearn (Googlers teaching Googlers) courses on topics like time management, mindfulness, and productivity.
  • I raised my hand when opportunities came up at Google for Startups to deliver workshops and trainings to entrepreneurs in our network, including to diverse audiences in markets like Dubai, Johannesburg, and Zurich.
  • I collaborated with the Google Primer App to create digital lessons on energy management and sustainable productivity that could reach thousands.
  • I spoke on behalf of Google at conferences like The Next Web in Amsterdam and Web Summit in Lisbon providing a glimpse into Google’s internal culture and how the company tries to prioritize employee well-being while maintaining high standards of team performance.
Google’s PR team wasn’t too thrilled with this headline

Basically, I tried to use the platform I had at Google to my full advantage, all the while helping others.

(Sidebar: I recognize most companies are not like Google and most jobs don’t provide this much room for experimentation. Even so, I’ve witnessed that there is usually more latitude that you realize to do things you care about in the confines of your “day job.” Often you just gotta ask!)

Find Work That Feels Like Play

The more I tested this approach, the more I started to sense I had found a sweet spot. By that, I meant I found (a) a problem I enjoyed working on and (b) work that I was naturally good at.

My quest to find this sweet spot started back in 2017 when I became obsessed with asking myself, “What am I doing when I feel most alive?”

This question was running like a radar in the back of my mind, constantly scanning through my experiences and looking for clues. It wasn’t obvious at first, but as I started teaching and facilitating, I started to notice how energized I was by the process.

There’s a nugget of wisdom from investor and entrepreneur Naval Ravikant in which he says:

“Find work that feels like play.”

I realized that sharing my learnings through teaching and facilitating workshops was just plain ol’ fun for me in a way that it wasn’t for everyone.

I loved preparing for these workshops, blending insights from different sources and domains and making them accessible and practical.

I loved facilitating, where I was able to share my own knowledge and also learn loads from participants who offered up their perspectives and insights.

I loved refining, rehearsing, and continually trying to make these workshops more engaging, interactive, and above all, impactful.

I just loved this stuff.

Slowly, I recognized this could be a competitive advantage for me. I had found work that felt like play to me. I had found that sweet spot.

With a problem to solve in my mind and work I was excited about, I set my mind on leaving Google to start my own thing.

Checking out on my last day at Google!

Part 2: The Money Question

As I thought about leaving Google, one of the biggest questions that loomed in my mind was this:

“Can I earn a living working for myself?”

Like anyone with a well-paying job, I found the financial security was hard to leave behind. In the past year, I’ve had countless conversations with people who are thinking of starting their own thing and money is always a central concern.

The good news is that it’s absolutely possible to make a good living on your own. In my first year, I took home just shy of £50,000 (full breakdown below). It wasn’t Google money, but it’s early days. Plus, I had much more fun, more freedom, and more flexibility. Can’t put a price tag on that!

It’s important to call out that my perspective is unique given I started a service-based business. If you’re launching a startup or building a product, your time horizon for profitability will obviously be different.

Here’s how I approached answering this question for myself.

My Backstory

I want to start by giving some context on my background.

I grew up in an affluent, upper-middle-class setting in suburban Minnesota. This is a very privileged starting point in life. My dad ran his own business in the construction finance industry and my mom spent most of my childhood looking after her three kids.

Things changed for us big time in 2008 as the financial crisis crippled the construction industry and my dad’s business went from thriving to life support almost overnight. Eventually, it couldn’t withstand the shock and he had to declare bankruptcy.

This taught me that while money isn’t everything, not having it is.

Fast-forward to 2013 when I graduated from college and was looking at $50,000 in student loans. This pile of debt made me rethink my priorities for possible career paths.

Instead of pursuing the world of non-profits and NGOs, where many of my fellow classmates majoring in International Relations would wind up, I recognized I needed to look more broadly.

Luckily for me, I stumbled into a job at Google through a community outreach program in New Orleans they were running and that I volunteered to join. That fortuitous opportunity led me to a role after school at Google NYC.

Working in tech was a blessing in the years after college, both financially and professionally. I made enough money to pay off my loans quickly and I was also exposed to a whole new world of business, startups, and innovation.

As the years went by, and I moved from Google in NYC to SF then finally to London, I started to notice one creeping downside. The longer I stayed, the more I earned, and the more difficult it felt to leave.

This is commonly referred to as the “golden handcuffs.” This is that feeling like you can’t walk away because the money is too good. The longer I stayed, the more I was promoted, and the more I earned. The more I earned, the riskier other options outside of Google became.

I recognize the insane amount of privilege in this whole idea, but I am only speaking from my own perspective and experience.

As I thought through the financial risks, I started asking myself what really mattered to me when it came to my work.

What Are You Optimizing For?

In every moment, we are making choices and optimizing for some known or unknown inner value. I have found that the easy things to optimize for are social approval, financial security, and comfort.

Our culture places value on those who make good money, work at prestigious companies, and appear “successful.” Forsaking a financial goal for a personal goal—like working in the service of others—isn’t always easy.

As time went by, I started to notice a shift in my inner compass.

What I realized was that teaching allowed me to be in the service of others while also learning and improving myself. Service and personal growth are core to my values, and doing work in alignment with them felt incredibly rich and rewarding.

I knew I could keep doing teaching and facilitating with 10–20% of my time at Google, but when I really dug deep, I knew I wouldn’t be satisfied if I didn’t give it 100%.

With that realization, I made a choice and decided to optimize for more time, more freedom, and more flexibility to do what I loved doing.

Getting clear on what I was optimizing for at the outset of this business has been invaluable. Because I know I’m indexing for personal growth instead of financial return, it helps guide my decision-making on a day-to-day basis and keeps me grounded when things get tough.

Setting a Realistic Money Goal

When I left, I decided to set a simple goal that I could use to benchmark whether or not my idea for a business was financially feasible.

I thought that if I could make £40,000 in revenue in year one, then after taxes and expenses, I’d be left with something like £30,000 in profit.

That’s roughly a starting salary in London, and I decided to anchor my expectations on that number rather than trying to match my existing Google earnings.

The good news is that I earned just about £100,000 in revenue, so well beyond my expectations. (Full breakdown below)

People have different approaches to goal-setting. Some believe you should aim high, others believe in setting realistic targets you’ll feel good about exceeding. It seems like the majority of people I know fall into the first camp.

My view was different, shaped in part by my belief that I was entering a long-term game. I looked at year one as almost a test of Minimum Viable Product, and £40k as a basic indicator of whether I was in the realm of meeting a market need.

Again, I came back to the question of optimization. In starting this business, I wanted to optimize for personal and professional growth, freedom and autonomy, and a career where I could serve others.

While money matters as one metric, I didn't want it to be the only metric on which I judged my success, especially in the first year.

Now that we’ve covered some of my thinking that led me to leave Google, let’s have a look at my business in more detail.

Part 3: Business Breakdown

As I mentioned above, my work is focused on helping leaders and teams thrive in the busy, chaotic, and ever-changing modern workplace. I focus on topics like sustainable productivity, time management, mental resilience, and well-being.

The main offering of my business is facilitating live workshops and teaching cohort-based courses, and that is where I’ve earned the vast majority of my income.

I also delivered lots of shorter keynote talks to businesses and coached a few clients 1:1.

What corporate workshops look like these days

For year one, I bucketed my workshop offering into four parts:

  • Make Time — a framework that helps you focus on what matters every day
  • Search Inside Yourself — mindfulness-based emotional intelligence training born at Google
  • Adaptive Resilience — mindfulness-based resilience training designed specifically to meet the challenges of the pandemic
  • Rise Above — custom workshops covering a range of topics from mindful productivity to remote working

Make Time

Across the year, Make Time was definitely the most appealing to clients I worked with, which wasn’t surprising given focus and time management became crucial topics for businesses during the pandemic.

My first paid workshop in April 2020!

Rise Above

Behind Make Time was my own custom Rise Above workshops. This part especially fun for me, as it pushed me to be more creative in addressing specific client challenges.

Some of the custom workshops I’m most proud of designing and delivering in 2020 were:

6-Part “Self-Management” Workshop Series

  • The six sessions were developed for a group of startup founders in a Google-run program and covered Mental Thriving, Physical Thriving, and Emotional Thriving.
  • I co-developed this program with the help of my partner (business & life) Claire who worked almost full-time with me for 4 months last year.
  • We drew on a blend of research and applied tools in the realms of productivity, well-being, personal leadership, mindfulness, resilience, and emotional intelligence to create this series.

Mastering Remote Time Management

  • This 90-minute workshop drew on my personal experience of semi-remote working during my time at Google and was delivered to a variety of corporate and startup audiences.
  • Being able to help people transition to the new norm at the start of the pandemic was a really rewarding challenge.

21st Century Mindfulness

  • I developed a 6-week course for a client that brought a fresh, modern approach to the fundamentals of mindfulness.
  • I found I particularly enjoy taking topics that people might otherwise think “it’s not for me” (i.e. meditation and mindfulness) and making them accessible and interesting.
  • This is one that I might create an online course around, so watch this space.

Search Inside Yourself

The final part of my offering was the Search Inside Yourself (SIY) program, which I originally taught at Google and now am certified to teach externally.

While I did teach a number of keynotes on SIY, this program wasn’t taken up by many of my clients. I think the primary reason is that SIY was designed as an in-person, 2-day experience. It took a while to transition the format to online, and it’s still a lot of content (~12 hours) to take in virtually.

Adaptive Resilience

The good news is that the Search Inside Yourself Leadership Institute released a new program in 2020 called Adaptive Resilience.  I’ve taught this twice in 2021 already and I believe it will be an increasingly attractive offer for businesses as the pandemic’s impact on employee well-being, stress levels, and overall satisfaction continues to be felt.

The Numbers At-a-Glance

Here’s a breakdown of various metrics covering the timespan of March 2020 through to April 2021.

Paid Workshops & Keynotes:

  • I delivered over 50 paid workshops and keynotes.

Free Workshops & Keynotes:

  • I delivered over 15 free workshops and keynotes.

Newsletters & Articles:

  • I sent 47 editions of my weekly newsletter One Percent Wisdom and published 17 articles on my blog.
  • My newsletter started with zero subscribers and currently has 565.

1:1 & Group Coaching :

  • I facilitated over 60 coaching sessions.
  • This included one long-term client (6+ months), two medium-term clients (1–3 months), and four text-based habit coaching clients.
  • In addition, I facilitated a variety of group coaching and one-off individual coaching sessions for corporate clients.

Financial Metrics

Here’s a breakdown of my Profit and Loss:

  • Total Revenue — $120,944
  • Total Expenses — $55,932
  • Total Profit — $64,736

If you convert the total profit into GBP, it’s roughly £46,957.

To put that into comparison, I earned £101,025 in the previous year at Google or £72,480 after taxes. Note that about 25% of that £72k came in the form of stock grants, so that figure isn’t quite accurate of my “take-home” pay.

Suffice to say, I’m pretty happy with this!

I’m confident I can grow it this year, and honestly, making less money but being so much more excited about my work has definitely been worth the trade-off.

Regarding expenses, these cover a diverse set of costs: content licensing fees, software subscriptions, contractors/consultants, website developers, lots of takeaway coffees, etc.

(Sidebar: if you’re curious about specific costs, just DM me and I’m happy to share more info.)

One caveat here is that my personal expenses were so low in 2020 due to the pandemic. This was a blessing as I didn’t draw any income from the business until 2021, so my savings went a lot further.

It’ll be interesting to see how I feel about this level of income once the world of travel, restaurants, and entertainment opens back up.

Part 4: Lessons Learned

There is a great quote from the best-selling business book “The E-Myth Revisited” that I think is accurate:

Business is like a dojo, a place you go to practice being the best you can be — Michael E. Gerber

In many ways, starting your own business is a great way to challenge yourself, learn about yourself, and grow. Your weaknesses, as well as your strengths, all come through in the way the business operates.

Here are a few lessons I’ve learned throughout the year plus some growth areas I’ve identified going forward.

✅ Lesson 1: Surround Yourself with Great People

I’m basically a “solopreneur” in that I’m the only person working full-time on this business at the moment. Even so, I have learned that you need to surround yourself with great people if you’re going to succeed.

I have so many people that helped me in the past year, it would be impossible to list them all, but here is a shortlist of the superstars: Claire, Tony, JZ, Natalia, John, Hector, Ben, Sanjiv, Dritan, David, Thomas. There are many more, so sorry if I’ve missed you!

Even if you’re working solo and aren’t asking for direct help on your business, there are a variety of ways I’ve sought inspiration and support. For example:

  • I have standing meetings with fellow entrepreneurs and friends where we’d discuss our businesses, share challenges, and problem-solve together.
  • I call, text, and email countless people in my network with questions on everything, from creating contracts to pricing online content.
  • I have weekly “Getting Stuff Done” calls with my mate Seb.
  • I have weekly “Learning Call”s with my mate Ronald to think about big ideas, mental models, and other concepts we can apply to work and life.

✅ Lesson 2: Keep Adapting, Keep Changing

They say change is the only constant, and whoever “they” are is right. I had a rough idea of my plan when I left Google in February 2020, but none of my ideas accounted for a global pandemic. My initial hopes of teaching and facilitating in-person events faded fast, and I needed to adapt.

Luckily, I found that I was quick to adapt. I worked such a variety of roles at Google and things were constantly changing, so I think that prepared me well for the total upheaval the pandemic put before us.

✅ Lesson 3: You Don’t Need to Do It All

One big benefit I had in starting up was my ability to offer two well-established programs to clients: Make Time and Search Inside Yourself.

While they are very different offerings, they both have established credibility and proven impact. Not only did I feel incredibly supported by the teams behind each program, but it also helped have these “pillars” that I could build up my custom programming around.

✅ Lesson 4: Stay Connected to Your Community

People always tell you how important your network is, but I really saw it firsthand in year one. It wasn’t an easy or immediate process to start this business. People didn’t approach me off the bat.

Even so, my first few clients were all through direct personal relationships. These were people who trusted me, saw the value I could bring, and took a chance on someone starting something new. I’m super grateful for that trust.

✅ Lesson 5: Take Care of Yourself

I honestly don’t know how I could have managed 2020 without consistent exercise, yoga, meditation, and sleep. When things got bumpy, when I felt completely overwhelmed, these practices brought me back to the ground.

Often, I had to remember to put my oxygen mask on first. That often meant stopping work even when I felt I “needed” to push through, heading outside for a walk, and reenergizing with a bit of movement and nature. Basically, walks are just the best.

🏔 Growth Area 1: Respecting My Edge

I definitely found my edge for how much I can teach and facilitate in a week, and sometimes I pushed too far. Overall I think this is a good thing, but in the weeks where I felt the edge, it didn’t feel good. It felt exhausting.

I realized when I’m that drained, my default is to push through and work harder when what I actually need is rest and restoration.

Laptop-free weekends, long walks, yoga, meditation, quality time with Claire and with my close friends — these are the medicines that worked.

🏔Growth Area 2: Leaning Into Sales

This area is somewhat paradoxical because on one hand, it feels like I sold better than I thought I would, but on the other, I still don’t feel I have a process nailed.

Over the year, I’ve learned that sales is an art and a science, and there’s so much room for growth here. Importantly, I recognized that sales does not have to be a dirty word.

I’m offering something I know is valuable, and my job is to find people who could benefit from that help. Yes, that is “sales” but as this mindset shift has occurred, it has helped me approach the process in a way that feels more human, more natural, and more “me.”

🏔 Growth Area 3: Putting Myself Out There.

I’d say “putting yourself out there” is really just marketing. As someone who started their career in marketing, I would have thought this would be easier.

The main challenge was getting clear on not just what I offer, but what benefits it provides to businesses. It turns out that doing that for a brand or a project at work is much easier than for yourself, at least in my experience.

A secondary challenge was my reluctance to invest in social media. I’ve loved being distant from platforms like Instagram for the past few years, but I also see the need to put more effort into sharing what I’m up to.

I’ve recently launched a YouTube channel, slowly started wading back into Instagram, and I’m keeping active on Twitter. Let’s see where that takes me in 2021.

🏔 Growth Area 4: Balancing Saying Yes and Saying No

I consciously chose to approach my first year with an experimental and open mindset. I wanted to try things, open myself up to new opportunities, and see what feels good. Even so, I probably said yes too much to things I knew wouldn’t create that much value.

This is an area I’m looking to develop in the coming year, specifically in creating more rules and principles for myself so I can create a more thoughtful decision-making process.

One heuristic from the legendary Derek Sivers I want to keep in mind is simple: Hell Yeah or No. Life is too short and time is too limited to invest my energy into things that I’m not a Hell Yeah on.

Conclusion: Your Turn

If you’ve read this far, I’m impressed. That was a lot of words!

If you have, I’m guessing you might be considering a similar move. While I can’t say with certainty it’s the right decision, and I honestly say that if you have been thinking about it this much, it’s probably a sign you should go for it.

If I were you, I’d probably take any advice in this article with a huge pinch of salt. After all, I’m still basically a rookie and your values and circumstances are different than mine.

However, if you are looking for a few final words of advice, here’s what I can say.

💰 Save Up.

I personally saved about a year’s worth of expenses before I quit my job so I would have a financial cushion. I’m not sure if that’s exactly the amount you need, and I know it’s not possible for everyone, but consider it.

One mindset shift that helped me to spend less was thinking that each dollar saved was a time unit of freedom. Instead of feeling cheap when I skipped a meal out, I considered it an investment in my future freedom.

🏎 Test Drive.

You wouldn’t buy a new car without taking it for a spin, and I wouldn’t recommend you start a new venture blind. Whatever type of work you’re interested in, find ways to test doing it now. It’s the best way to verify the assumptions that otherwise might only live in your imagination.

📊 Find the First Client.

This is more specific advice for a service-based business like mine, but it probably applies if you have a product-based business too.

If you can land your first paying customer before quitting, you’re going to a) have some real-world data that you’re solving a need b) feel more confident in taking the leap and c) that confidence can translate into a stronger start out the gate.

Thanks for reading.

If you have any questions about my experience, send me an email at connor@connorswenson.com and I’ll try my best to answer!

👋 If you want to stay in touch, connect on Twitter or join my weekly newsletter.