SUMMARY: In this essay, I’ll walk you through the steps I took to assuage my fears and gain the confidence to quit my job and move to San Francisco. Assessing the current tech landscape and my place within was an important first step on my journey. Then, I’ll explain how I compared defined opportunities to the esoteric idea of quitting my job and moving to San Francisco. I’ll lead you through the process of developing financial confidence and easing into living creatively. Lastly, embracing self-doubt and seeking constructive support is a pivotal, ongoing exercise that I practice and will describe in detail. Reading time - 13 mins, 43 sec.

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In June 2012, I quit my job, moved to San Francisco and “took the plunge”, so to speak, and finally did it…I fully invested in myself.

One of the most lucrative investments we make is in ourselves. Forget stocks, real-estate, commodities, and other assets. The most lucrative investment of all is the one that gives you an opportunity to create freely, full-time, with no distractions or unwanted external pressure.

Like a newborn that gazes at something full of wonder, without judgment or expectation, you will see great things happen if you commit to returning to this child-like state. You’ll find not only what you love to do, but also what you’re meant to do.

As an engineer who loves creating new things to help people, I have always wished to have the the time and opportunity to live this way.

Entrepreneurship and artistic lore is full of stories on why many chose to take the proverbial plunge and double-down on their dreams. However, little has been written on “how”. What were the steps they took to be in the right frame-of-mind to do it? How did they make their decision? Perhaps it’s fitting…it might be a bit contradictory to read a blueprint or look to another for instructions on self-actualization.

Contradictions aside, for my inaugural essay here, I’d like to share with you how I mentally prepared and rationalized investing in myself so I could live a fully creative life for awhile. Like any risky, attractive investment, there’s boundless upside, but the journey may be tumultuous. Understanding how risky and unnerving it could be, I spent a good six months preparing. Here’s what I did.

Surveying the Landscape

At the outset, one of the toughest obstacles to overcome was dealing with nebulous fears about the job market on the whole. Fears about things that were beyond my control—namely macro-economic forces, especially in tech, and how I could be in jeopardy of joining the ranks of the unemployed or under-employed in the current economy. Some questions that raced through my mind were: is the current environment supporting creative tech entrepreneurship? Could we be in a bubble?

After gathering data and speaking to respected people, I realized that macro-economic fears and questions such as these weren’t so important. The forces at play between the overall investment and market climate in tech as well as consumer demand for products were so far removed from my own individual sphere of influence. In essence, my own skills and impact would be the leading indicator of success, not overall aggregate factors. Fortunately, I am in the tech industry, which isn’t as vulnerable to global economic factors as say, finance, or parts of the federal government.

It quickly became apparent that what really mattered was my own personal landscape of opportunities and if my experience and skills gave me the tools to seize these opportunities. How would I be perceived in my space? Would I have credibility to find opportunities to succeed? Was I experienced enough?

The only way to test this was to immerse myself in the market. I traveled to the Bay Area often and met startup founders who were looking to grow their teams. Fortunately, there were interesting opportunities and ideas people needed help to build. It gave me objective, real-life assurances and feedback that there were many exciting roles that might be right for me. Accordingly, the anxiety about the environment I’d be diving into subsided.

The bears morphed into bulls in my mind. My fears subsided and I came away not fearful of whether I could find an opportunity, but it became more about what was the right opportunity. Learning about my own deficiencies and where I could improve was an added benefit of the process.

Finding When You Were Happiest

Surveying the landscape led to a number of options. All seemed to have their merits. So, I was faced with a conundrum…how do I objectively weigh them against one another? To add a nasty twist, how could I weigh those all against the most risky, amorphous option: taking the plunge and going at it alone?

My initial process for evaluating these options was fundamentally flawed.

Unfortunately, I let the lizard, reptilian brain take over. Instead of looking inward to see what would make me happiest, my evaluation of each option depended on how others would perceive my move. It’s the default way many look at climbing the proverbial career ladder: How will this look on my resume? Will I be perceived as successful?

I don’t mean to suggest that what others or society at large thinks about you is completely irrelevant. We are a social species, constantly looking for little reassurances and positive feedback that we are going in the right direction. It’s a deep need that reaches even the smallest things we do (we all can relate to the excitement and contentment that arises from many “likes” and positive comments on one of our random Facebook postings).

However, just looking externally is a dangerous proposition. You may end-up becoming what others want you to be rather than what you want yourself to be. If external factors are your only barometer, you expose yourself to ever more competition with many people competing for the same scarce resources and rewards. I felt like the rat race just required me to work harder and harder to claw my way to the top, which has pretty weak marginal returns holistically. It’s better to set and meet your own metrics of success.

Dissociating your internal wants and desires from the equation often leads to disaster. I know perhaps a few too many that live a life of perceived achievement from another’s vantage point only to be personally unhappy with what they do or wishing they were doing something else. I needed to reconcile the two. If not, my individuality and freedom of expression would be hindered by external perceptions.

Analyzing all my experiences and memories became my single priority. I looked at every project I had ever done and everything I had ever shipped. Which experience had the best combination of positive impact, creative spirit, and camaraderie with others?

Searching for when I was happiest led me to a familiar place. My backyard, in the early 90s, was the Microsoft campus. Basketball became my first love and I often played on the courts amongst the sprawling buildings merely two miles away from my childhood home. Exposure to technology and innovative people became inevitable. Growing up in this tech boom, what should have been an ordinary suburban upbringing became unexpectedly vibrant.

Inspired, my friend, Emmett, and I started building websites for local businesses when we were 13. Some modest success followed (Flash intros and HTML before CSS, anyone?). Without realizing it then, it was my first taste seeing the pace of Internet growth creating demand faster than technologists could support. So, we acquired the skills that could scale these demands.

Since then, I’ve been seeking to return to an experience like this. All my favorite projects since then have been an attempt at returning to these roots. Working with people I like, in a fast-paced environment, where ideas from inception to implementation are ours is quite amazing. It became clear that taking the plunge, the amorphous option, was the right one for me.

Getting Your Financial House in Order

Next, I did the more mundane, yet important objective analysis of where I stood financially. One of the biggest obstacles throughout this whole process was getting a clear picture of my financial health and how much to budget so I could live creatively. It was also by far the biggest source of stress. At any given moment, I would wonder, do I have enough money saved to do this? How much runway is enough? How can I minimize risk and avoid unexpected financial losses?

In order to alleviate this stress, thoroughness was key. The first step was to simply consolidate my accounts and positions. It’s surprising how over the course of employment the many separate financial institutions you may need to use to accomplish your goals. From high-yield savings accounts, checking accounts, credit cards, loans, and investment portfolios (personal and from your employer), when income is coming in, your overall liquidity may be low since capital is tied-up.

Planning to live with no income is at odds with this approach. The metric that needs to be optimized is the amount of time you have to create. From my perspective, any unwanted risk that could jeopardize my runway liquidity needed to be minimized or removed.

Once I consolidated and increased liquidity, it became time to dissect my own personal burn rate. A spreadsheet of data outputted from my Mint account became the easiest way to keep track of my discretionary and non-discretionary spending. I also spoke to many people in San Francisco who gave me insight into what a monthly living budget might be.

Some back-of-the-envelope data…San Francisco is an expensive city. Expect to spend $1300-1600 per month on rent, on the higher end if you don’t start looking a few months in advance and decide to not find roommates. Although many locals will complain about public transport, it’s quite manageable with no car to get to the major tech hubs, although it does take becoming familiar with the trade offs of buses vs. trains vs. walking for a given route. If you plan on exploring the Valley weekly, budget $150 per month for trips on Caltrain to Palo Alto, Menlo Park, Redwood City, and Mountain View. If you are no good at cooking, budget $800 for food, $400 if you plan on cooking multiple times/week with some eating out like me.

If after analyzing your finances the total runway is shorter than you expected, you can make some adjustments. You can cut down on your discretionary spending, increasing your savings rate and consequently add to your available runway. After a few months of optimizations and tinkering with my budget, I was able to get more comfortable with my financial outlook and confidently take the plunge.

Consuming Less and Creating More

Consuming content is now so easy and ubiquitous that we forget that it may have a downside. Our own creative muscles may be getting weak, slowly making us ill-equipped to do the deep analysis and innovative work that drives value in the future.

Luckily, creative capacity can be improved. Just like it’s an outlandish expectation for someone who never runs to do a marathon immediately, it’s probably an outlandish expectation for you to paint the Sistine Chapel tomorrow. Fortunately, there are a myriad of easy ways to create content on the go to practice and hone your creative mindset.

Evernote, an app available on all platforms and devices, was crucial in helping me do this. I pledged to use any spare moment to write and verbally record my thoughts in the app. A few minutes here and there—waiting in line at the store, riding the bus—compelled me to want to spend longer periods in my spare time fleshing out ideas and writing essays like these. Each idea became more well thought out day-by-day, collateral for intriguing discussions with other technologists that created excitement and optimism to take the plunge.

To further support the goal of consuming less and creating more, I substantially cut back on the amount of time a day I spent blogs and news. At first, it was tough, but as time went on it made much more time for long-form reading, like books, that offered more depth.

Spared some of the banal and trivial characteristics of the tech echo chamber, my perspective became more broad when necessary and naturally acute along topics that really interested me.

A transformation occurred in how I view content. I found value in the longer-form essay that I now appreciate once again. If you’re still with me here, it’s why I’ve decided for my personal blog to author essays, and not posts, to give the reader not only more data and depth, but ample turns and opportunities to reflect.

Seeking Support and Embracing Self-doubt

The journey outlined above is a lonely one, no doubt. Knowing this would be the case, it was a useful exercise to practice working alone for extended periods of time again. Some of the most value created in my past projects and ventures required long, extended periods developing depth and understanding. Depth allowed me to appreciate the details and how to correctly differentiate my creation, which made it scarce and valuable.

After taking the plunge, whether you like it or not, you’ll have even more alone time. The standard hours that people are at work you’ll be alone. When most people are going out and having fun, consuming products and content after earning money, you may also have to be alone.

Folks champion the heroic story in tech about someone who set off by themselves on some Odyssey-like quest, building and creating then returning to bestow upon the world the fruits of their labor.

Reality is a bit more nuanced than that. Products aren’t launched in a vacuum. Mentors and a support network play a huge part. When I inadvertently go into hero-mode, I remind myself that I only have two hands, two feet, two eyes, two ears, and one brain. There’s only so much I can know and do. People are inherently social and need a few people to support them along the way. Finding them and keeping them close is pivotal.

Understanding this, and herein lies possibly the most important lesson learned, don’t take the plunge without a support group. Here in San Francisco, I’m surrounded by a few of my closest college friends also working on their own projects. Not only is it important as an emotional keel, but also as a sounding board for your ideas. A quick feedback loop is absolutely necessary.

But even the most rich and loving support network can’t be with you always. Left to your own devices, self-doubt will creep-in. We all feel it and it’s often hard to discuss openly.

When the inevitable self-doubt rears its ugly head, realize that it’s completely normal! In fact, it might even be necessary to force lines of inquiry to test your assumptions and decisions. You’re not the only one who has self-doubt. It’s universal.

I’m not sure if this is psychologically or scientifically true, but my own experience tells me this: self-doubt, at its core, is an emotion stemming from a weakness you know and feel about yourself. Address that weakness right away.

For me, when I feel it creeping in, I write it down. It instantly makes me feel better (often, when it is staring at you in black and white, you’ll see how absurd and trivial it might be). Then, I’ll see if there are steps I can take to dissolve that doubt. It may be reaching out to one of my peers or mentors for help. It may be I just need to learn one little skill that I know I need. It may mean I just need to call a close friend or my family to gain some confidence. Like most emotions, know that it’s fleeting. It’s only temporary and it too shall pass.

Taking the Plunge, Finally

My hope was that I could complete the above in succession, neatly. However, the necessary outcome—confidence in my decision by subduing fear and doubt—like all subjective matters of the heart, proceeded in chaotic fashion before reaching equilibrium.

One day, everything felt right. My finances seemed to be in order and budgets validated. My creativity sharpened through practice, giving me confidence I could build again. My support network all seemed to validate my assumptions and my decision. My own inner self-doubt seemed to fade. And I did it.

I’m now in San Francisco, living creatively and working on ideas. Come join me and reach-out on the left or leave a comment. I’d love to hear from you.