Leading up to that day, I spent the past 12 months hatching a plan to resign from my employer. After graduating in 2009, I went into management consulting, which many people call “finishing school for MBAs.” With several great years of consulting under my belt, I felt ready for a change. Despite having been promoted in January 2013, I still aimed to quit the firm without a job, take some time off to recharge, and return refreshed to explore new opportunities in Silicon Valley. In the year leading up to my resignation, I saved money aggressively, read about entrepreneurship, and tried to expand my network in my spare time. After ensuring that my bonus had landed safely in my bank account, I resigned. My boss asked me to stay to wrap up some client work and transition. I agreed, effectively giving them a very generous 2-month notice.
That was over a year and a half ago. Over this past year, I have had many amazing experiences, learned much about myself, and gained a better appreciation of the workings of businesses and non-traditional career paths. In reflecting on that time, I’ve grouped my experiences and observations into a few themes below.
Entering the jungle
At the outset of my drive home after my final day, I felt incredibly free. Halfway through the drive, I began thinking about what I would do next.
That’s when panic set in.
When friends asked me what I would do after quitting, I told them I would lock myself in my bedroom for a week to play video games non-stop. I envisioned myself re-emerging from my cave after that week, rubbing my eyes as they once again became accustomed to the sun, and re-entering society to proceed with whatever came next.
What struck me during that drive home was that, if I followed my plan, I would have quit my job and started to burn through my savings to do the most ridiculous thing possible: binge on video games. This thought struck me particularly hard because I had just spent many months carefully watching my bank account balance. So that plan was instantly thrown out.
Instead, I began furiously planning, reading, meeting up with friends, and attending networking events. My plan allowed me one month in SF to plan my trips over the next 3 months and enjoy free time in the city. To make the most of it, I began waking up early before my alarm, packing my schedule full of activities, and trying to learn as much as I could to prepare for whatever future path I chose. Every day was exhilarating.
On a very tactical level, I wondered how I would deal with the complete freedom, not having any work-related constraints and deadlines. Would I lose motivation and slack off every day? Or would I maintain discipline to get everything done in my ambitious plans? Being very aware of this potential slippery slope, I tried putting structure in place in various ways. I scheduled meet-ups with friends, signed up to attend professional talks, and developed a daily routine.
While I didn’t adhere to everything entirely — workouts were easy to skip and getting out of the house before 10:30am felt difficult — trying to put some structure in place helped. I realized how hard it is to maintain discipline without any outside constraints put on me. Every day became an exercise to consciously improve my discipline and level of organization.
Plotting a path
During my 3 months of traveling, I reflected on what I wanted to do upon my return to SF. Eventually, I landed on the interim answer of doing independent consulting as I looked for full-time jobs.
Initially, I had entertained the idea of starting a business. However, I quickly realized that I didn’t have a network to recruit people and I didn’t have a compelling idea. Facing these two major strikes, I crossed this idea off of my list. Creating a start-up isn’t nearly as easy and exciting as it seems on the surface, particularly when you actually sit down to think about it. Who knew?
In the process of identifying a new path, I weighed a few considerations: keeping the cash flow going, figuring out what kinds of jobs appealed to me, and building my network within the Valley. While being a generalist consultant and constantly doing new projects certainly appealed to me, I wasn’t sure that I wanted to continue doing it by joining a corporate strategy team. But I didn’t have a clear idea on what the various functional roles in tech were. Additionally, I realized that while there are a lot of jobs available, the level of competition in the Valley is very high. My former employer and clients have no brand recognition among recruiters, and I didn’t have a useful book of contacts from my prior work experiences.
Working as an independent consultant seemed like the perfect fit for a number of reasons. I could do interesting projects to learn various functional skills, get new logos on my resume, get to know interesting people in tech on a professional level, and have time to apply for jobs. Most of all, it would provide income while I went through this learning process.
Great! I now had a plan.
Now came the hard part: selling consulting work.
Preparing to bushwhack
“Second prize is a set of steak knives.“
To prepare to sell, I reflected on my experiences in helping my consulting firm partners prepare for sales discussions. For consulting work, the sales process was a consultative one and the sales cycle could be fairly long. Initial conversations could lead nowhere for months until a sudden acute need arises, or conversations may lead nowhere at all. However, every conversation was a great learning and relationship-building opportunity. Conversations in the consultative sales process involved providing value to potential clients before any contracts are signed. I needed to act as a sounding board and help potential clients structure their thoughts. Fairly straightforward in concept, but less so in execution.
Now to find the people to have conversations with. Attending professional talks and networking events, I tried to meet a variety of people, see what their business problems were, identify how I could help, and convince them that they should trust me … all while trying to not sound like a used car salesman. Many people at smaller companies either didn’t have problems that outsiders could help with, didn’t have budget to pay me, or weren’t in positions to hire. Also, people who attend networking events oftentimes are looking for jobs or looking to sell things to other attendees. Professional talks were better because they drew professionals who could benefit from the topic.
Even when I did meet someone who could hire consultants, it was difficult to build a deep professional trust with strangers. People are guarded, and rightfully so. There are many people in the world who are long on self-promotion and short on substance. How could I convince them that I was different and that they should trust me? In the span of a 10-minute conversation? Particularly when they were a deep functional expert, say in Product Marketing, and I had no direct experience in their realm?
I reflected on the difficulty that my former firm’s partners had in selling to potential clients outside of their networks. At the time, my partners had relied solely on existing relationships to sell work. They hadn’t yet figured out how to sell work to potential clients with whom they had no prior relationship, despite holding various panel discussions and publishing well-read articles. Thinking about their struggles made me re-consider how much time I should spend on attending networking events. That being said, I’ve met some great people in these various talks and I continue to try to add value for them where I can to build the long-term relationship.
That left me to focus on reaching out to my network. The experience of reaching out left me humbled and gave me a very deep love for my friends. Whenever I met up with friends, I would always jokingly tell them that they should call me if they have any strategic work they need done, have a nice laugh, and follow it up with, “But seriously, call me.” As more people began to hear about my plans, leads started to slowly roll in. My friends really kept me in mind when they heard about interesting opportunities.
At the outset, when I told people that I was an independent consultant, I felt like a fraud because I didn’t actually have any clients. I thought about a joke that my friend made about his former colleagues who quit their jobs. Some of them just wanted to take some time off and had no job lined up. However, they felt too ashamed to tell their bosses about their real reasons. To save face, they all claimed, “I’m pursuing entrepreneurial opportunities.” My friend joked that it was such an empty thing to say, but it sounds very serious and official. In the Valley, there’s a major question that wantrepreneurs ask themselves: “Is my idea a business or a hobby?” Many people claim that an idea is only a hobby until you have a real product that people are buying. And even then, it’s still only a hobby until you can make enough money to replace your regular source of income. In terms of my situation, I realized that any joker can claim to be an independent consultant, but it’s not real until you have your first client.
That feeling of being a fraud instantly dissipated when I landed my first contract. After I spent two months networking, a good friend of mine from business school hired me for a month-long contract.
Cutting a path on one’s own
Starting my first project as an independent consultant, I quickly came to appreciate the many soft skills that my bosses in the consulting firm had mastered. My bosses continually went into new client organizations to meet the unique cast of characters, understand the clients’ personalities, map out the politics, build allies, and establish credibility and trust with suspicious employees at the client site.
While I had watched my bosses during this initial process of sniffing out the client, I had only ever contributed to parts of it. I had never done the whole thing myself. As I met everyone at my first client’s company, I felt hyper aware of the need to observe the company’s cultural norms, quickly build rapport and establish my credibility. Being an introvert, I found this process to be mentally exhausting. Every night for the first month, I fell instantly asleep when I got into bed.
In building these working relationships with people at the client site, I oftentimes had to dispel negative impressions about consultants and teach people how they should work with me. The mention of the word “consultant” conjures up negative images for many people. To outsiders, the joke is that consultants borrow your watch to tell you the time, then walk off with your watch. Also popular are references to the movie “Office Space.” Two consultants, known as “the Bobs,” are brought into the protagonist’s company to cut costs (read: plan layoffs). The jokes made by insiders, namely consultants and people who hire consultants, get to a deeper reality. In the most cynical sense, consultants produce nothing more than slide decks. The stereotype goes that after consultants deliver a final presentation to the client team, a series of congratulations are made to both clients and consultants for their hard work, an expensive end-of-engagement dinner party is thrown (almost always at the client’s expense), and the client promptly puts the slide deck full of recommendations onto a shelf to collect dust, never to be reviewed again.
To explain my line of work, I often borrow a medical analogy told to me by another my friend. Consultants are like doctors for businesses. When businesses are sick, they call in consultants to diagnose the problems and identify treatments. After treatments are recommended, consultants are sometimes kept on the team to coach the client as they put these recommendations in place, much like a physical therapist helps injured patients exercise their way back to health. That, and a couple client work examples, usually helps people understand what I do.
After I set the stage, I was able to get back to the familiar ground of executing the analysis.
Understanding the law of the jungle
When people first hear about my independent consulting work, they often comment that it must be nice to be my own boss and have lots of flexibility to take time off whenever I want. I agree that those are certainly pros.
But I’m quick to explain the cons. As a consultant, I’m not actually my own boss. I’m not so overbooked with business that I can turn down engagements. I feel incredibly lucky, grateful and humbled to have such good friends who trust me enough to send business my way. Time off is often unplanned. Between my last project and my current one, I inadvertently took a month and a half off. It can be a feast or famine business, with little visibility into how long the famine will last once the current project ends.
Becoming familiar with the feast or famine nature of independent consulting has been a very intellectually gratifying, and sometimes nerve-wracking, experience. In his book Antifragile, Nassim Nicholas Taleb, writes about how salaried people succumb to “the turkey problem,” an analogy about incorrectly inferring that tomorrow will look exactly like today and yesterday. The turkey, as the analogy goes, comes to love the farmer because every day from the time he was born, the farmer comes to feed him. Based on this past evidence, the turkey assumes that whenever he sees the farmer, it’s a happy occasion. The turkey’s beliefs about the future are true, until the week before Thanksgiving when the farmer takes the turkey to the slaughterhouse.
Likewise, salaried people oftentimes assume that their jobs will always be in place and are ill-prepared for turbulence or variability in their income. They think that their income tomorrow will look like their income today, until they’re suddenly jobless. Then they have no idea what to do next and go into panic mode.
In contrast, Taleb cites taxi drivers as people who know how to deal with income variability. The variability of their daily earnings can be quite large, particularly when contrasted with salaried person’s earnings which have zero variability. If a taxi driver isn’t finding any fares in one part of Manhattan, he’ll drive to to different parts of the city until he begins to find business. The salaried person has no such luxury.
Working as an independent consultant has helped me better understand “the turkey problem” in my own life. At a rational level, I knew from the outset that trying to sell consulting work would be an emotional roller coaster. And it was. But internalizing this belief on a deep emotional level and backing it with experience is a much more thorough understanding than just inferring it on a rational level. During my inadvertent 1.5 month break from consulting, I noticed how my emotional state changed and evolved. Upon finishing the contract, I was euphoric during the first 3 weeks of unemployment, very confident that I would quickly find another job. From week 4 onward, I slowly devolved into a state of panic. When I was awarded my next contract, the panic subsided into relief. On a rational level, I understood that it was only a matter of time before I found something interesting if I kept networking and applying for jobs. But rational understanding provides only cold comfort. Having gone through this roller coaster several times, I feel that I have greater emotional fortitude to handle such situations in the future.
Also valuable is my better understanding of the contracting economy. Previously, I had only experienced full-time employment. I had no idea what types of short-term opportunities existed. After having done this for a year, I know where to poke for opportunities, understand how to structure discussions about projects, have a list of client references, am top of mind among my network of friends and clients when project work comes up, and have a real hourly rate that I can cite confidently.
Returning to civilization
After a year of working as an independent consultant, things turned out better than I could have imagined at the beginning. I had no idea whether I would be able to sell any consulting work when I started. I’ve learned a tremendous amount from my project work and from the sales process, which will serve me well as I progress in my career. I’ve been mostly employed, which is more of a testament to how well my network of friends treats me than to my own ability to sell. I’ve built out my network in the Valley, getting to know many amazing people on a professional level. I’ve had plenty of time to become familiar with the types of companies and personalities in the Valley, through attending talks and working as a contractor. And I’ve had plenty of time to think about what I want to do and apply to full-time jobs without feeling rushed to find take any job that comes my way.
However, I realize that I’m missing out on a number of experiences as a consultant. I don’t have the opportunity to build an organization. I only advise, I don’t operate. I won’t be able to manage people directly. Until there’s a deep trust in place, I’m limited to doing projects in functions that I’m already familiar with.
Also interesting is seeing different people’s reactions to my decision to work as an independent consultant. Among the business school crowd, nobody really knows what to make of what I did for the past year. Some people are very complimentary and say that it’s gutsy to strike out on my own. Others are less certain of what to think. Some very honest friends are negative on my decision. One friend told me, “If I were dating you, I would tell you, ‘What the hell is this independent consulting? You need to get your shit together!’” Another friend reacted in an unexpected way when I told her that if any of her friends were interested in contract work, I had some interesting leads that I was happy to pass on. She responded in a huff, “All of my friends have full-time jobs. They’re not interested in contract work.” Understanding these negative reactions was very eye opening, since I’m sure that I will encounter these views again.
Now I’m ready to return to full-time work. While on a rational level I’m confident that I’ll find something interesting, on an emotional level I cower at the uncertainty inherent in the job search process. At the end this 12 month experiment, I’m very thankful to have had these experiences. And I’m excited about what the job search will bring.