How To // Win Celebrity Apprentice

Things that I love: Reality TV, business, being tan, making money.

It should be of no surprise that I am obsessed with Celebrity Apprentice. Donald’s perma-orange skin and Ivanka’s awkward body language get me every time… I can’t get enough. Despite all of the criticism against The Donald, I admire and appreciate the Trumps. I wear Ivanka’s shoes and respect Donald’s real estate acumen. He’s been socially relevant for almost 30 years and seems fine with being portrayed in the media as a caricature of himself. He’s made no apologies for his politics or his hair. The man has golf courses and books and neck ties and his whole apartment appears to be made of gold. We can all learn something from him.

I am proud to say both of my roommates have told me, without provocation, that if I were on The Apprentice, I would win. And you know what, I think I would too. Here’s how I’d do it.

With a stylist and a glam squad, I would rule the world. 

Before I even leave the house each morning, I've already made dozens of mini decisions. Pumps or flats? (How much will I be walking today?) Hair up or down? (Is it windy outside?) Dark lip or neutral? (Do I plan on eating anything in the next 12 hours?) There is a lot to consider and I’m exhausted just thinking about it. If I had someone to eliminate those questions for me, I could invest my energy into something more productive like reading the news or looking at Instagram. Worst of all, this effort depletes our decision making energy for the rest of the day. 

The phenomenon of decision fatigue explains why some of the most creative and successful people, like Steve Jobs and Karl Largerfeld, subscribe to a daily uniform. The outfit is pre-planned so no thinking is involved while getting dressed. This also explains why when presented with two options, we have a difficult time following through with the more difficult choice, if there is an easier or more familiar alternative. For example, how many times at the end of the day have you thought: 'Should I go to the gym or stay home and eat tator tots?' If you are not in the habit of going to the gym, making a decision that is outside your norm is much harder; you’re not used to it, you value comfort and routine. Besides, you used up your decision making energy at Starbucks that morning- latte or cappuccino. When going to the gym everyday is a habit, a part of your routine, it’s harder to break your routine and NOT go.

Real World Application: Keep a routine for your morning. Have an arsenal of outfits already arranged. Keep your work makeup and hair neutral, easy and quick. Listen to the news while you get ready. And drink your coffee the same way, every day, at home, for goodness sakes.

With a stylist and a glam squad, I would rule the world, Part II.

Not only would a hair and make up team make my life easier, it would make me perform better. When we are well groomed and well dressed, we feel confident, act strong, and are perceived favorably. A good hair day is a good day. If I’m looking like a Pantene Pro-V commercial, you’re going to get the confident attitude that comes along with being a hair model. Since people like people they find attractive, and people like to work with people they like looking good when you go to work and you will get you far. 

Real world application: Obviously, groom yourself and dress well. But more importantly, stand up straight. Throw your shoulders back. Look alive and be alert. When you need a real power boost before a big meeting or interview, do a power pose. It works. 

The *: Don’t take it too far- if the focus at work is on your outfit or your cleavage, you distract from your achievements and abilities. People don't like people who are TOO attractive, so tone it down, sister.

Identify and play to your strengths

This part takes a bit of preparation work, before you get on The Apprentice. The fact of the matter is, if you're not an absolute rockstar in your field, you don’t belong on this show. This is not a show about mediocrity, it’s a game to raise obscene amounts of money for charities and deliver outstanding business ideas that real life companies can implement. This is not a joke. 

(Edit: This is me taking reality TV too seriously. #noshame)

If you aspire to join the upper echelon of the business world and hang out with DT, find things in the professional realm that you enjoy and are comfortable with. Then exploit the hell out of them. If you like being in front of a crowd, use every opportunity to do so; join Toastmasters and prepare speeches in your free time. Great copywriter? Sweet- get a side gig and practice. You’re a salesperson? Read, practice and actually sell ice to an Eskimo before you make claims that you can do so. I want to see proof of sale, buddy.

Then when the opportunity presents itself, pounce. DO NOT, I repeat, DO NOT volunteer to be a PM for a project you know nothing about! Is Geraldo Rivera the right guy to market women's shoes? Hell no! Should Leeza Gibbons be the MC at an event where she’s speaking without rehearsal? Hell yes!

Real Life Application: Ask your friends and co-workers what they perceive you to be good at. Often times we have trouble identifying our own talents; things that come naturally to us might actually be disguised as talents you didn’t know you had. (Make the feedback reciprocal, of course.) Then delve into your craft. Get great at what you’re good at. Master your skills. 

Deliver on the task at hand. 

The fundraising episodes KILL ME. On these episodes, DT will pit the two teams against one another and confuse them by telling them they have to sell pies or hotdogs or pizzas for charity. But really, he always closes with: “The team that raises the most money wins.” The contestants that get fired on these episodes fail to deliver on the task at hand. Consider this:

  • It is a fundraising task. The team with the most money wins. This means, your focus is on RAISING MONEY. Focus and deliver on the task at hand: fundraising. 
  • Presumably, you are a celebrity. You should have more connections than the Average Joe- connections who need a tax write-off and can purchase a macaroni necklace for $10k. (It’s for charity.) The most surefire way to get fired on The Apprentice is to not call your richest friends when you're doing a fundraising event. Focus on the task: fundraising.
  • If you're trying to raise money, what is the fastest way to do it? Selling 20 pies for $5 each or selling 2 pies for $5k each? Work smarter, not harder. Focus on the task: fundraising.
  • If the goal of the task is to raise money, nobody cares how much love and effort you put into baking your cupcakes. Focus on the task: fundraising.

Real Life Application: Focus on the task at hand. If you’re not clear on the objectives, expectations or deliverables, ask for clarification. If you’re the one delegating the task, it’s always important to explain the “why” to your team. The “why” provides context and helps unite a team in understanding the goals of the corporation/company/project. This ensures they’re moving in the right direction. Most importantly, use your time wisely; expend effort and time in a way that satisfies the most important goal. Hours on the phone calling big donors will get you money, spending all of your time decorating donuts will not.

Don’t hold back.

Honestly, I don't really know what the point of being the Celebrity Apprentice is. Do you get a job? What do you do? Apparently you have to beat out all these other celebrities for the title, so it seems important. I guess the winners get to come back and be an advisor on later seasons, like Piers Morgan & Joan Rivers did this season (RIP Joan.)

Regardless of what the job duties of The Apprentice actually entail, DT demands his apprentice be a bad ass. If you mentally check out, you will be fired. If you want a bullseye on your back, forget to call in your richest connections to donate money. If you want to go home, cause drama and let it make you incapable of working. If you show a moment of weakness and someone spots it, you're gonna get called out, even if you legitimately have bad cramps. (Sorry Shawn Johnson.)

You have to give it your all, non-stop. If you want to hold the elusive title of The Apprentice, The Donald expects you to relentless, inspired and results-oriented. You are expected to leave your drama at the door, crush your competition and inspire the industry. And you’re supposed to stroke Donald’s ego and make him look good. Big hint here: Your boss wants the same from you.

Real world application: Take care of yourself. You clearly don’t live to work, but if your life outside of work has you coming in hungover and half-awake, I guarantee someone will notice. They will exploit your weakness and you will be off your game. If you have excuses, a bad attitude or an unwillingness to work hard, In your boss’s eyes, your stock plummets. If your chronically out sick with a cold, you can’t be counted on. Your stock plummets. If your conversations have more to do with your personal drama than the task at hand, your stock plummets. 

Trust me, I’m a boss. Show up to do the work and give it your all. Shut up and stop complaining.

Take No Prisoners.

Here’s some sage advice: “If you don’t look out for Number 1, you're going to step in Number 2.” A little tidbit from renowned philosopher Rodney Dangerfield… You're welcome. Anyway, if you’ve seen the boardroom, you know that it’s ruthless. You have villains (Omarosa, Piers, etc.) you have deflectors and shit-stirrers (Teresa Guidce, Melissa Rivers, etc.) and then you have crazy Gary Busey. There are a lot of personalities at play and you need to have an exit strategy for every kick and punch that gets thrown at you. Remain calm and be political. 

In these group tasks, you have to ensure that the people are managed before the project can get done. You’ll need to size up your competitors quickly, identifying their strengths to leverage their talents and get projects accomplished. But most importantly, you have to think about how THEY think they can attack you. 

Even when you’re not the Project Manager, everyone should have a clearly defined role and some level of accountability towards a specific function or deliverable. Be ruthless about complimenting people’s talents and guiding them towards their success… or their demise.

Most importantly, let people melt down on their own. In high pressure situations, most people get emotional. When you get emotional, you lack the ability to think rationally. Think about who you’re trying to impress- the ever cool, facts and figures focused CEO- Donald Trump. He responds well to rational people who can communicate effectively. Let the crazy ones hang themselves out to dry.

When DT asks you: “Who should get fired,” your answer will be, “If we lose and someone needs to get fired, the person to be fired will need to be the person who was responsible for the reason we lost. If the whole thing was determined to be a cluster, then the PM has to go.” Be accountable and you will be praised; most people refuse to take personal responsibility for anything, so you might have to assign responsibility to them. Be honest and you’ll be okay.

Real World Application: You need to exploit your team in the best way possible. If you have someone that is a rockstar at Task A, do not assign them to do Task B. Clearly communicate your expectations and desired outcomes. Manage the way others perceive you by staying calm. Do deep breathing exercises in the bathroom stall when you have to work with lunatics. Rise above. And for the ones that need to get fired, give them just enough rope to hang themselves. 

You have to know that you can't win them all.

No team has ever won every single task assigned to them on The Apprentice. Whether it’s giving a presentation or pitching an idea, you’re not always going to hit a home run. Let other people shine. The thing is, if you mess up, it doesn’t mean you’re bad. It doesn’t mean you’re unlikable, unsuccessful or unworthy. Those are stories we tell ourselves in our heads when we internally overreact to rejection or confrontation. Just because someone labels you as a bitch doesn’t mean it's true. (It might be a little true, but who cares.)

Get comfortable with uncertainty and get comfortable with risk. Put yourself out there but be okay when not everyone falls in love with you. Know who you are- you are a multifaceted business person who gives 110% whenever they are faced with a challenge, right? Your the person that reads blogs like these to try to be better, right? You take risks, are creative, crazy and fun, right? If you get fired, big deal. You were on The Apprentice and Donald Trump knows your name. You done good, son.

Real World Application: Don’t be so hard on yourself.

To my fellow competitors on future seasons of The Apprentice… I’m ready and I’m coming for you. And to all the #girlbosses and #boybosses out there, the illustrations you see above are borrowed from Sophia Amoruso's book #girlboss which you should purchase because we both graduated from the same high school and she's an inspiration. 

xoA