by Jenny Blake
Career experiences are important, but they are not sufficient for landing your next opportunity or client. Prospective bosses and business partners are looking for marketable skills that lead to results, giving you a reputation as a must-hire.
Let’s explore these key experience elements that you bring to the table.
Work Experience
Your prior jobs may have more in common than you think. For example, working as a server in a restaurant and as a sales representative are not such dissimilar roles. Both involve building relationships quickly, working with a range of personality types, learning how to address and anticipate customers’ needs, and getting comfortable with irregular pay.
Consider your last five to ten jobs or projects, even those that did not earn income:
What were the key activities associated with each role?
List between five and ten unifying themes among these jobs and projects.
Now get more specific: What are the related skills, results, and industries on your list? Themes might include: departments (such as marketing), job responsibilities (such as people management or teaching), key projects (such as creating systems or brand strategy), or key activities (like financial modeling or coding).
Marketable Skills
A marketable skill is a specific service you provide at the intersection of talents, strengths, and education that a customer or company will pay you for.
Even better are two marketable skills that might seem unrelated, but that complement each other in a unique way. For example, if you are fluent in a foreign language and you have a background in accounting, you might be a prime candidate to work for the FBI.
Identify the marketable skills you have already developed. What do people currently seek you out for?
As in the FBI example, do you have two (or more) marketable skills that intersect in a unique way?
Look for clues in the exercises earlier in the chapter. Often what you loved to do as a child and activities that fall into your Zone of Genius inform the marketable skills you are using today. Which of these interests are you not yet applying to their fullest potential?
Results
Results are the meaningful impact that you have had on people or projects. These can be qualitative and quantitative, whether improving existing systems or launching new initiatives. Qualitative results might relate to soft skills, such as leadership and teamwork, while quantitative results are often characterized by increasing effectiveness, efficiency, revenue, or reach, or a combination of all of the above.
What specific results have you helped people or organizations achieve?
What are your most significant work projects to date? What was important about each one?
What professional accomplishments are you proudest of? Why?
Reputation
When you consistently help others achieve results, you develop a reputation as a must-hire. Reputation refers to how others see you, the strengths they recognize and seek you out for.
The most agile pivoters, whether entrepreneurs or employees, hardly have to look for work; they have a reputation that makes them easy to spot and desirable to hire. Clients pursue them, and are often willing to wait to work with them or even recruit them away from existing full-time positions. When seemingly bad things happen, their bounce-back time is quicker than average because they know who to call, their skills are in demand, and their reputation makes others feel fortunate to work with them.
In what areas have you developed a strong reputation, personally or professionally?
What skills are you best known for among friends and acquaintances?
What types of assistance or advice do people ask you for most often? What do they end up walking away with, beyond what they initially asked for?
What awards, accolades, and public praise have you received?
What do you want to become a known expert in?
______
By emphasizing strengths in the Plant stage, you will see that you are not starting from scratch. Still, there is a big difference between dreaming about a pie-in-the-sky, theoretical pivot and making one happen in real life. The latter requires facing the reality of the world we live in: life costs money. How will you pivot without sending yourself into a panic?
CHAPTER 4: FUND YOUR RUNWAY
What Is Your Timeline? How Can You Earn Extra Income?
[M]oney is only a tool. It will take you wherever you wish, but it will not replace you as the driver.
—Ayn Rand, Atlas Shrugged
"I SPENT MY ENTIRE TWENTIES TELLING MYSELF I WAS GOING TO DO SOMETHING, THEN NOT DOING IT,” Andrew Deffley said when I asked him what brought him to Manhattan for an acting audition. “This time I am following through. I quit my job two months ago and am giving myself six months to try to earn a living acting, which I have loved since I was a kid.”
Andrew had been working at NFL Films as a production manager for eight years. He had a brand-name gig, but hit a wall when he turned thirty and felt there was more out there for him. Deep down, he had always harbored a vision of being in front of the camera as an actor, not hidden behind the scenes as an editor. Tired of succumbing to his fears, Andrew pivoted on his strengths and experience in video production and began taking acting classes and auditioning for roles, knowing that even if he failed, he would be happy he tried.
Andrew didn’t just have passion, energy, and excitement. He also had a financial plan.
BUILD A SOLID FINANCIAL FOUNDATION
For a time, the online business zeitgeist was “Quit your job! Work from a beach sipping coconuts! Outsource everything!” However, once the adrenaline of the big leap wore off, reality quickly set in for many people who realized they were running on fumes in their energy levels and bank accounts.
Change is challenging enough to navigate without financial pressures. With them, it places a choke hold on your creativity and your options.
With rare exception, pivots require financial resources, or at least sound planning for a number of scenarios that may play out. The more you can clarify your resource needs and bolster your financial reserves, the more options you have for making your next move.
You might want to take a “pre-cation,” time off before starting a new job. You might want to go back to school, or do long-term traveling. Maybe you just need time to slow down and reflect. By clarifying your financial needs through the exercises in this chapter, you can proceed to later Pivot stages with a sense of which risks you can afford to take and when.
Andrew knew he wanted to try his hand at acting as a career after an “aha moment” during his first acting class in 2010. Before launching into it full time, he planned for how he would support himself throughout his pivot. He didn’t just quit his job and hope the universe would pay his bills. He saved up enough for a six-month break from his work with the NFL to test his hypothesis that acting would bring him professional happiness and enough income to support himself.
Even if he spent every penny of his financial runway, Andrew knew his experiment would be a success. No matter what outcome resulted, he would know that he had given it his best shot. If acting did not pan out in six months, he would keep auditioning, but he would add a more consistent side gig doing production-related work to tide him over financially between roles. This approach is significantly different from the starving artist model of, well, starving indefinitely while praying for a big break.
PIVOT FINANCE 101
This section covers common business and finance terms adapted for planning a pivot, whether you are starting or running your own business, working a “side hustle” in addition to a full-time job, or looking to pivot within your company.
A caveat: Although some worst-case scenario planning is helpful in case you get laid off or lose a big client, it is more sustainable to build a sound business model, capitalize on marketab
le skills, and find steady income than it is to just sell-sell-sell or scrimp and save until your bank account is barren. As former Google CEO Eric Schmidt once half jokingly, half seriously remarked during a company all-hands meeting, “The answer to all known problems is revenue.”
Monthly nut: How much do you need to earn each month to cover your basic expenses? When I work with people approaching a career pivot, I ask for three numbers:
Minimum needed: to cover rent, utilities, groceries, and basic expenses.
Nice to have: to maintain something close to your current or desired lifestyle; might include shopping, meals out, hobbies, weekend trips, and the ability to fund long-term savings.
Jump out of bed with glee: this number lets you do anything on your lifestyle wish list without hesitation, such as long-distance or long-term travel, large or luxury purchases, or having an abundance of resources for charitable donations or to support extended family.
Business strategist Nick Reese calculates the ideal monthly nut a person needs to pay living expenses (and taxes, if self-employed) as 3.4 times their monthly rent or mortgage. For parents, or for people living in expensive cities, the multiplier is 5. For bootstrappers willing to live frugally or “lean,” the multiplier can be 2.5 times rent.
To calculate your yearly nut, multiply your monthly rent by 41. If you have debt, such as a mortgage, Reese suggests multiplying your monthly rent or mortgage payment by at least 50.
Crunch Your Numbers:
What is the amount of your monthly nut, calculated using the formulas above?
What is your yearly nut?
What are your total average monthly expenses for the last twelve months? How does that figure stack up against your monthly nut?
Runway: How long will your savings support you if you do not earn any income? The rule of thumb for emergency funds used to be three to six months until recent years, when the average unemployment duration hit thirty-one weeks, or nearly eight months. When I left Google, my cash runway was equivalent to six months of living expenses, which is consistent with many other pivoters I spoke with. I had other assets, such as a condo, a car, and a 401(k), but did not count them as part of my runway since they were worst-case scenario cash-outs.
If you do not currently have any savings, your runway is likely too short to make any major moves that might require time without pay, at least without also taking on more risk. Part of your Pivot plan may include increasing how much you earn (something we will cover later) or how much you set aside from what you are currently earning, possibly delaying bigger moves and risks until you have more flex in your financial system.
Crunch Your Numbers:
How much do you currently have in cash savings?
How much do you have in other assets?
How many months will your cash savings last if you are not earning any income (total savings divided by monthly nut)?
Burn rate: In Silicon Valley parlance, burn rate is defined as the rate at which an enterprise spends money, especially venture capital, in excess of income. In pivot terms, are you being financially prudent or spending like the Wolf of Wall Street? The higher your burn rate, the faster your runway will disappear. During a pivot, cutting back on nice-to-have lifestyle indulgences, such as meals out and shopping, will buy you more time to strategize and build your business or land your next gig.
Bridge income: The term bridge loan refers to short-term commercial real estate financing. A bridge loan is meant to be paid back quickly, bridging the timing gap while investors implement their plan to improve a property’s performance before securing a long-term loan. Bridge income tides you over while making a change, but is not your desired primary long-term solution.
Although your savings can act as bridge income, this is not ideal for two reasons: savings are a finite resource, and the more you spend, the more you may stress out, impairing your ability to think creatively. Treat your savings as a backup account that you only dip into if your bridge income fails.
Bridge income creates stability as you test other income avenues. Figuring out a source of bridge income and steady cash flow, either part time or on the side, puts the power in your hands and will make you more confident and agile when you do make a change, or if change chooses you.
In identifying bridge income, we are going for consistent cash flow, not a Hail Mary, a long shot with much greater risk. Now is not the time to bet big on a passive income play to build a business that earns money while you sleep. Something like that is fine for a longer-term move, but only if you can offset it with more reliable income in the meantime, or are willing to burn through your savings runway to build it.
Trading time for money often gets a bad rap. However, if you exchange services based on existing skills to paying customers, you can buy time for implementing longer-term or higher-risk aspects of your pivot. For some, bridge income might come from a part-time job such as bartending, temping, or freelancing. My most stable, reliable source of income comes from one-on-one coaching, whereas keynote speaking and corporate training pays much larger sums but tends to be more sporadic, with a longer lead time and invoicing period.
No matter what your current employment status, if you were to suddenly find yourself self-employed and had to make it for a year, how could you add value to any market? If you had to implement the following three streams of income right now, what would they be?
“So you can breathe” income: hourly wage, possibly projects below your skill level
Mid-level: monthly retainer, steady cash flow, part-time work
Big bets: high income potential; big contracts, clients, or job offers; income sources with longer lead times but greater reward
Side hustle: This term refers to modern-day moonlighting, earning income on the side while maintaining a full-time job. This is often not sustainable indefinitely, though some people will be perfectly happy with a light side hustle, like making and selling jewelry or doing freelance design work for friends, that brings them joy without having to quit their job. Even entrepreneurs can have side hustles, or creative sandboxes to play in outside of their main revenue-generating activities.
My mom’s advice for me growing up was, “You should always know how to support yourself.” As a result, I always make a point to know where my money is going, how to bring in a steady income, how to invest wisely, how to pay my bills, and what my backup plans are.
Since the day I started earning money consistently in college, I have always had a second source of income on the side. Whether it was getting paid to take lecture notes in college, babysitting, doing web development tutoring over the phone for small-business owners, coaching, or working on my first book, for the first ten years of my career before striking out on my own, I always had my main paycheck and my “hustle” check.
My version of freedom is being able to make choices in my best interest. I do not ever want to feel trapped in a job or relationship because I can’t afford to leave due to lack of savings or earning ability, two areas I can directly influence.
Side hustles represent a calculated risk: you willingly invest some of your spare time (and maybe money) into a project that you are excited about, with the hope of making a greater proportion of your living off this someday, or to land your next full-time role. To take a side hustle full time, you need to identify the bridge income within it—the marketable skill, product, or service that will pay the bills most consistently.
One of my friends, Kit, loves fishing. When he finds a good spot in the lake, he refers to it as a “honey hole.” The honey hole is the secret spot he can return to that is likely to yield a great catch. The best side hustles are your equivalent of a honey hole: you enjoy them, you are excited to return, you have discovered something unique to you, and they provide value in return.
There are four criteria to developing a strong side hustle:
1. Cash (flow) cow: If it does not create income, either now or in the future, your beloved side hustle is a hobby. The best side hustles will demonstrate a monetary return on your investment, if not now, then at some point in the not-too-distant future. How long are you willing to wait? I suggest experimenting with a side hustle that allows you to test revenue generation fairly quickly.
At first, the income you earn from your side hustle is likely to be labor intensive. You will invest time and sweat equity for little pay. In his Startup School podcast series, Seth Godin calls this “front-loading.” Better to do the hardest work up front, then reap the rewards later, he says, rather than be surprised down the road when you have much more at stake.
2. Market reach: Your side hustle should offer a solid amount of growth potential. If you love teaching underwater basket weaving, but there is no one interested in learning it, you will be quickly catapulted back into unprofitable hobby territory. Look for side hustles with a sizable market to serve, yet not so broad or undifferentiated that you have difficulty resonating with ideal clients.
3. Enjoyment: A side hustle doing grunt work is valuable if it helps you pay the bills or save up for the next big trip you want to take. But a side hustle with even better potential is one that emphasizes your strengths and makes you excited to work on it, whether you have fifteen minutes to spend that day or five hours.
4. Skill building: Ideally, your side hustle will also help you learn or improve skills that may be needed in your field in the coming years. Think about what skills, if you were to develop them now while this is a side project, would serve you well if you took these activities full time. Some are universal and can benefit you in almost any role or business, such as sales, marketing, copywriting, technical coding or troubleshooting, and design.
