CHAPTER 5: BOLSTER YOUR BENCH

Who Do You Already Know? Who Can Provide Advice? What Can You Give in Return?

He will have friends from whom he may seek counsel on matters great and small, whom he may consult every day about himself, from whom he may hear truth without insult, praise without flattery, and after whose likeness he may fashion himself.

—Lucius Seneca

NETWORKING. IS THERE ANY TERM THAT GIVES MORE PEOPLE HIVES WHEN IT COMES TO CAREER CHANGE? One study revealed that the word itself actually makes people feel dirty.

You have probably heard phrases like “Connections are currency” and “Your network is your net worth”—clichés repeated so often that they are easy to cast aside. Yet it remains true that authentically connecting with others is a far superior opportunity-building strategy than “spray-and-pray” outreach or résumé blasting across online marketplaces.

Nearly everyone I interviewed for this book mentioned that, in addition to excelling in their current roles, career opportunities came from two key places:

Both of these factors hinge on creating two-way conversations with people you already know and those you have yet to meet. I remember speaking with an executive, Sam, at a conference. After my keynote, he approached me to share the story of his most recent pivot. He had worked at one job for twelve years before taking the risky move of leaving to work at a start-up. Nine months later he was laid off.

Shell-shocked and worried about supporting his wife and children, he started placing calls to his network the same day he was fired, on the commute home. Within two weeks, Sam was starting at another job. The speed of this transition was based upon several factors:

I am not here to tell you to eat your networking spinach. Rather, this chapter covers specific tactics you can use to authentically put yourself out there and develop a robust support system for connecting with people in a way that excites, not drains, you.

The strongest people strategies involve a blend of the following:

EXPAND YOUR SPHERE OF INFLUENCE

Shawn Henry worked his way up from an FBI file clerkship at twenty years old to a leadership role as the “number three guy” at the bureau—the executive assistant director—by the time he retired. Shawn pivoted thirteen times within the FBI over twenty-six years, each time expanding what he calls his sphere of influence.

Rather than stick to the traditional job ladder for his role, rising in the ranks as a bureau chief, he moved into emerging fields based on his strengths and interests. Shawn maintained a short-term vision each time; he focused on mastering the skills required for the role he was in and the impact he could make, incrementally increasing his level of responsibility and his ability to influence a greater portion of the bureau. By the end of his tenure, Shawn had become a key figure in creating international cybersecurity protocol.

Shawn encourages others to be cognizant of what their sphere of influence is, whether as a janitor or the president. “By examining your sphere of influence, you have the ability to quantify what you are doing every day,” he said. “There are very specific times in my career when I remember engaging with people where I know my being there had an impact. Whether quietly working behind the scenes or standing in front of the camera, I looked for opportunities to affect people, policies, and processes.”

That sphere of influence does not just magically appear—you have to actively pursue those opportunities. “People always say it’s a small world. That doesn’t just happen,” Shawn said. “The world becomes smaller when you increase your circle and make that happen. It’s a huge world for someone sitting on the couch watching TV every night.”

BUILD A NETWORK OF COLLECTIVE BRAINPOWER

Change does not happen in isolation. Even something that feels solitary, like training for a marathon, becomes much easier with friends and family checking in from time to time to hold you accountable and cheer you on throughout training and the big day.

As Adam Grant revealed in his book Give and Take: Why Helping Others Drives Our Success, there are three types of people: givers, takers, and matchers. Those who are most successful in their careers are givers who help others freely, without expectations, and thereby establish goodwill, reputations, and relationships that enhance their success.

Impacters, though driven strongly by their own learning and curiosity, are givers at heart. For all of the categories below, consider yourself not just high net growth but high net giving, and you will reap rewards on both sides of the coin.

One-Off Mentors and Shadowing

Standard career advice says make sure you find a mentor. However, in practice this can be intimidating. Who? Where? How? Will people say yes to a mentoring relationship if I reach out? Rather than pressuring yourself to find one Holy Grail Mentor, start by setting up one-on-one conversations with people you admire, people doing work that interests you, and peers who might also be able to provide sound advice (and vice versa).

Given that you may not have the specifics of your pivot figured out yet, start with wide-ranging outreach. Approach those you are intrigued by, and make a point to include people who are doing work that seems only tangentially related to what you are currently doing or might want to pursue.

A one-off mentor is someone you admire who has achieved something you aspire to, or who knows more about an area of interest than you. Rather than awkwardly asking a semi-stranger, “Will you be my mentor?” or trying to start a long-term relationship with someone you hardly know, approach one-off mentors for short, targeted, fifteen- to twenty-minute interviews instead.

If your initial conversation goes well—you hit it off and you value their advice—you can always ask to follow up at a later time with updates or questions. Even if that person does not end up providing specific counsel on your next pivot, you never know where the relationship might lead, or how you could be helpful to each other later down the road.

People often tell me they are nervous about reaching out to someone out of fear of rejection. Keep in mind that the worst someone can say is no. A no is almost never personal to you. The person you approached may be focused on other things at the moment; prefer a different format than the one you suggested (i.e., a phone call instead of lunch); or, in some cases, giving specific advice is how they earn a living, so they may direct you to existing programs they offer. Chalk up every no as another successful outreach effort and keep moving. Many will say yes if they can, remembering everyone who helped them along the way.

Allow one-off mentorships to evolve naturally if both parties are interested in developing the relationship further. In some cases, the person you speak with may even offer to stay in touch, as one of my longtime mentors Susan Biali did with me nearly ten years ago. During our first call, she said she would love to support me on an ongoing basis, and asked if it would be helpful to set up a monthly check-in. I am deeply grateful for her counsel and our idea exchanges throughout my career, and for her believing in me from such an early age and stage in my business.

In other cases, you may be the proactive one in following up after having these one-off conversations. No need to harass or bombard; just start with sending a thank-you note afterward, then check in a few weeks or months later with an update on action you have taken related to your conversation.

Find people in roles that interest you, whom you could ask about their daily experiences, perhaps even by shadowing them for a day or more. This will help determine whether the realities of their work match how things appear from the outside. Does the reality of this role fit your strengths and interests?

That was my brother Tom’s approach with his first mentor, an accomplished real estate investor. After he graduated from UCLA, where he played football as a defensive end, Tom began attending football alumni tailgate events to network with real estate professionals, a group that was living his one-year vision. Tom asked one booster he admired if he could help manage his portfolio of commercial properties and apartment buildings without pay for a few months, in return for getting an inside look at his operations.

By starting with a shadowing arrangement, there was little risk to Tom’s potential mentor other than teaching time, and it helped complete a significant amount of work. Tom performed well and ended up parlaying that arrangement into a full-time role managing his mentor’s properties for two years. Bolstered by the base of experience he acquired from this apprenticeship, Tom then pivoted into commercial real estate brokerage and started investing in multifamily units for his own portfolio.

One-Off Mentor Outreach

1. Make three wish lists of people you admire: These are people with whom you want to develop deeper relationships. Consider:

2. E-mail three people from the lists above: Ask if you can speak with them for twenty minutes, or even send one short question via e-mail to start. Mention why you admire them, and why their specific advice would be helpful for you. The key here is making it easy for recipients to say yes.

3. Be curious: On your call or in your e-mail, ask open-ended questions, and let the other person do most of the talking. Ask what they would advise you to do in your situation, what they would have done differently if they could do things over, what the drivers were to their success. You can ask if there are any key resources that were particularly helpful, and if there is anyone else you should speak with.

4. Respect the time parameters you set: Do not go past your scheduled time. This will make them much more likely to be willing to set up a second meeting in the future.

5. Thank you, Part 1: Send a note describing what specific advice resonated, and the impact the conversation had on you.

6. Thank you, Part 2: Do something with their advice! Take action. Report back with a progress update on specific steps you took as a result of your talk.

Board of Advisors

As one-off mentoring relationships progress, you will develop deeper relationships with a handful of people that you can consult regularly and exchange ideas and feedback with, ideally to benefit them as well. In doing so, they can become members of your board of advisors. This is your brain trust, your mentor clan, your strategic “been there, done that” crew who offers lessons from their triumphs and missteps (both of which are invaluable sources of road-tested wisdom).

Although I have been fortunate to have several advisory board members proactively offer to support a particular pursuit, their participation usually came after I initiated the relationships by reaching out to introduce myself. I also make a point to place equal effort on my own reputation-building activities, so that when I do approach people, they will hopefully find me interesting to speak with as well.

You might assemble an informal board of advisors that you consult with questions without explicitly inviting them to be part of your team. Or you can do as Rebecca Rapple did with me and send a formal invitation. After I agreed to be on her personal advisory board, Rebecca sent a spiral-bound packet of her goals for the year in every area—a twenty-page life and business plan.

Sometimes your advisory board members will know each other and interact with each other, but most often they will not. That is okay; your board does not have to convene all at once. Still, they are a short list of five trusted people that you can turn to for advice when you get stuck.

Similarly, you may not have direct relationships with each of your advisory board members. You can still follow their progress, learn by observing what they are up to, and look to them as an inspiring part of your vision. Think of people you admire: perhaps you have no contact with them, but their actions and career approaches still serve as guiding lights. For example, many people swear by “the Church of Oprah,” whose talk show reached ten million daily viewers at its peak. These advisory board members from afar can be inspirational and aspirational, as you learn from their path by staying current on what they are doing. Just remember to also keep your eyes on your own paper and not get too caught up in others’ definitions of, or pathways to, success.

Drafting

If you have seen the Tour de France, you know about drafting: riders clumping behind the lead bike, not passing on purpose, so they can benefit from reduced headwind and effort. They are mimicking a technique used by many bird species. The lead biker or bird is doing the hardest work, while the others flock closely behind to reduce their drag and the energy needed to achieve the same speed.

Career drafting can be a mutually beneficial technique, though it should not devolve into stalking, stealing, plagiarizing, or leeching. Think of someone further along in their career, either in your industry or the one you may want to be in, who is doing what you are hoping to achieve, and ask if you can help with any overflow he or she does not have the time or desire to tackle.

This is not about being lazy. By drafting behind someone who has already cleared a way forward, you can learn from their approach and benefit from overflow they cannot handle. You will pay it forward someday by helping others draft behind you.

I was in a lead position when coaching other solopreneurs, people running their own one-person businesses. As I shifted toward working with executives and entrepreneurs, I referred anyone who reached out for postgrad coaching to several of my clients whose primary goal was working with young professionals. It was rewarding to pass these opportunities along to other coaches who were thrilled to have the work.

On the flip side, I drafted behind other professionals when I was building my speaking business. I told other speakers in my career niche that I loved working with organizations and speaking at conferences, and was happy to travel to do so. Several speakers were glad to refer me for gigs that did not appeal to them, or that they did not have time to take on, particularly those with small children at home.

The people you want to surround yourself with will endorse the adage that “a rising tide lifts all boats.” Andrew Deffley, from Chapter 4, drafted behind an actor who had ten years more experience by forming a genuine friendship with him. They kept in touch after crossing paths on various sets, and when the veteran actor landed a gig on a new web TV series, he recommended Andrew for one of the supporting roles. Based on this introduction and the strength of his audition, Andrew got the job.

Drafting can take several forms:

Friendtors

You have heard the adage that you are the average of the five people you spend the most time with. I say the more the merrier; but at a minimum, if you do not have friends that inspire you and help you expand, it is time to add new ones. There is no room for toxic people ever, but certainly not when you are making a major change. Pivots have a way of forcing these relationships to the surface so they can be dissolved or reconfigured with clearer boundaries.

Friendtors, on the other hand, are the amazing people we are fortunate to call friends, who can also wear the mentor hat professionally by providing domain-specific advice. You may have friendtors in your local area already; if not, start seeking like-minded people in online communities or meetup groups focused on your interest areas. Your closest friendtors may also be part of your board of advisors who you turn to when facing big decisions.

One of the most helpful actions that pulled me out of unproductive navel-gazing during a business pivot was setting up phone calls, coffee dates, and walk-and-talks with peers in my industry who had figured out solutions to major sticking points I was facing. Because we were developing mutually beneficial friendships, we met more regularly than we would have had the chance to with more formal “big fish” mentors.

These friendtor conversations provided many benefits: they got me out of the house and my own head, helped me connect with others, gave me real-time feedback and solutions to my specific issues, and uncovered new opportunities and ideas that I would not get from merely reading books and listening to podcasts.

I did not approach these conversations as “can I pick your brain” sessions—that phrase is a personal pet peeve—who wants their brain picked?! Instead, I saw these meetings as an opportunity to provide mutual value. I set an intention to enter those interactions with positivity, feedback, helpful suggestions, resources, encouragement, and connections for the other person, too.

Connecting with friendtors can become a habit just like working out, without feeling like a nausea-inducing form of networking. Set a goal to meet with one or two interesting peers every week. Make reaching out a regular part of your routine, whether forming new connections or revisiting with people you have met in the past. If you do not live in the same city to meet with a friendtor in person, it works just as well to set up a “calfee.” Yes, that is an amalgam of call and coffee—hat tip to my brother for that one!

Another way I catch up with friendtors is by organizing gatherings, events I refer to as “catchalls” because they allow me to catch up with many friendtors at once, and create value by introducing them to each other. Every summer I host Potluck Picnics in Prospect Park, and I encourage invitees to bring others. This allows us to casually connect with old friends and make new ones, all over low-key conversation and delicious food.

Luke Schrotberger turned to his friendtors when he wanted to pivot within his company, where he had worked for nearly ten years, from consulting on projects for defense manufacturing to a group that worked on oil and gas in Alaska. He started by reaching out to close friends inside and outside the company. Luke spoke with one friend who started around the same time he did and was now in a leadership role in Alaska and could provide honest insight and perspective. It was this conversation that ultimately helped him land the job and pivot internally.

Two years later Luke decided he wanted to pivot once again, this time to start his own company, since it seemed there were no more growth opportunities for him with his current employer. Two weeks after he announced to his boss that he was leaving, that same colleague who brought him to Alaska during his last transition made an offer for him to move to Australia to start a new division. Luke’s friendtor outreach provided critical insights during his first pivot, and a job offer at the next.

Mastermind Groups

In addition to casual friendtor relationships, I have also found great value in more formalized peer mastermind groups. For many years now, I have set recurring weekly or biweekly calls with one or two friends who are doing similar work or who share similar goals. These mastermind groups provide consistent accountability, encouragement, and brainstorm buddies.

I recommend finding people who are at your level, with whom you can have an even exchange of ideas, feedback, experiences, and introductions to others. Even if you are not in the same industry or do not share the same goals, these groups can provide a great source of accountability and support if you set those as the central aim.

I met Lora Koenig when she signed up for one of my courses, a ten-week program for generating momentum for a big goal. In that course, I assigned each person to a small mastermind group for weekly accountability check-ins. When Lora joined the program, she was in debt, unhappy with her job, longing to see the world, and wishing she “could just escape from life and start fresh.” Lora said, “I felt restless and miserable, that if something didn’t happen soon, I would be stuck in an unhappy life forever.”

That hopeless feeling made the trouble of change worth it, and sparked her to take three Scan steps at once: apply for the Peace Corps, sign up for a conference for creative types, and enroll in my course. Within six months of completing the course, Lora was accepted into the Peace Corps and pivoted from working in product management to agricultural development in rural Ethiopia.

“The peers I met really helped support me during this time, especially when I felt like I was crazy,” Lora said. “While people I knew at my job and in my city would say they didn’t understand why I wanted a change, my online peers were saying, ‘It’s okay to feel like this,’ and ‘It’s your life.’” For Lora and so many others I have worked with, finding a group of like-minded people online helped her feel less alone, less crazy, and more courageous.

My friend Adam and I hold a 30/30/30 call for 90 minutes, approximately every three weeks: one-third for catch-up, one-third for brainstorming for his business, and one-third for brainstorming on mine. Whenever my friend Elisa and I need extra motivation and accountability during busy times, we start an e-mail thread for the month, then reply at the end of each day with a list of work completed and what we plan to tackle the following day.

When my friend Alexis Grant and I were writing books at the same time, we set up a shared daily writing tracker. It was motivating to see each other’s entries and cheer each other on. A few months later we created a similar spreadsheet and invited people to join us for a challenge of writing 50,000 words in one month during the popular National Novel Writing Month held every November. We named ours NaNoBlogMo to fit our blogging aim, and nearly a hundred people joined. Aided by the power of group accountability, we wrote a combined 556,000 words, with four people hitting the 50,000-word target.

Knowing that my peers would see a goose egg if I didn’t write motivated me to get a little bit done each day. It was the first time in my life, and eight years of blogging, that I had written consistently every day, even when I did not feel “struck with inspiration,” something I had often waited for in the past.

A few things to keep in mind when setting up a mastermind group:

Bartering

If you are short on cash, or even if not, and you have a unique skill to trade for another expert’s services, bartering can be a way to get professional help while keeping expenses down. In a study of a thousand freelancers, 83 percent said they refer work to fellow freelancers, 52 percent team up on projects, and 37 percent trade services by bartering. Bartering agreements work best when there is a start and end date, and clear deliverables on both sides.

I have bartered successfully by trading my business strategy coaching with other coaches, a lawyer, a massage therapist, and a website designer. I even created a website in exchange for having a fee to a yoga retreat in Italy waived. All my barter buddies are good friends to this day, partly because we have been able to come through in the clutch for each other by exchanging expertise over many years, and throughout many ebbs and flows in our lives and businesses.

Bartering works best when you can benefit from a skill the other has and vice versa. This can be tricky; it is not always easy to find two people whose skills directly match up with each other, at the time when both are looking for help, and also have the time, energy, and financial flexibility to take on unpaid work.

Keep in mind that you want to identify a fair exchange rate; given that money will not be changing hands, it is important to determine what would satisfy both sides. Things can get weird (and fast) if the exchange starts to tip unevenly in one direction, or even if one person starts to feel like it does. For this reason, consider whether bartering really is best.

If you are building a business, you might want to pay someone neutral—someone you do not have a personal relationship with—so that you do not feel reserved when giving feedback or bumping up against inevitable creative disagreements. Barters should not be confused with actual business partnerships, which require greater commitment and do involve money or equity.

CAREER KARMA: SEEK RECIPROCAL SUCCESS

On several occasions, I have had potential clients approach me a bit hesitantly since they wanted to do work similar to mine. Would I still be willing to work with them if we are technically competing for the same type of client? “I don’t worry about that for a second,” I reply, often to their surprise. I am delighted to send them referrals, even to people who could just as easily work with me, because I fundamentally believe there is enough for all of us.

This is what I call career karma. When I give freely, I reinforce the idea that plenty is on the way back. Plant enough seeds of generosity, without expectation, and it comes back tenfold, often in ways you will not see coming.

Lisa Danylchuk, a San Francisco–based psychotherapist, calls this reciprocal transformation. “The principle of reciprocal transformation says that one person’s growth is another’s,” she says. “Learn to see the other person’s awesomeness or good fortune as a reflection of your own possibility.”

Sharing resources and celebrating others is a start, but not sufficient for reciprocal success.

Your ability to help others starts with you. You must fill your own cup first by asking for help along the way. Don’t just give until you are empty. Going it alone is tough. It is lonely, and most of all, it is frustrating.

I learned this the hard way. I once nicknamed my inner whip cracker “the self-sufficient warrior.” It represented the protective shell I built for myself early in my career and relationships. If I did things alone, I did not have to rely on anyone, and no one could let me down. I could handle and control my own happiness and success thankyouverymuch.

Except that it didn’t work. The more I protected myself, the further away people got. The more I tried to go it alone, the more burned out I became.

Conversely, when I got so low that I had no choice but to ask for help, the exact next steps I needed came to me. People entered my life at just the right time. I started to trust the wisdom that the events in my life had to offer, the perfectly timed unfolding of lessons that seemed handpicked just for me, no matter how challenging in the moment. I recommitted to the full cycle of giving and receiving.

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The best network-building strategy is not about making a landgrab for favors and business cards. It is about developing mutually beneficial, resonant relationships that do not feel like work; ones that bring you energy, ideas, and connections and vice versa.

People are a linchpin of your Pivot strategy . . . but it is not time to call in favors just yet. What will motivate others to connect you with opportunities before you even have to ask?