I love giving advice.

So does my friend Alex.

We come from different generations and we’re at very different points in our lives and careers. But we share the same philosophy: every door can be unlocked.

Every once in a while, we  partner up on a special installment of my advice column, Ask Ellen. It’s called… Ask Alex & Ellen.

Two hits of advice in one column.

We hope you enjoy it!

Dear Alex & Ellen,

I’ve always wanted to freelance. I’m tired of playing by someone else’s rules, hours and holiday requests. I’ve never ever wanted to climb any ladder because I’m just not interested, but climbing my own ladder? That I can get excited about!

My partner just got the job of his dreams, which means we’re moving to a brand new town—where I don’t have a job.

Part of me is thinking, “Hooray! Since we’re moving, this is the perfect opportunity to kickstart my freelancing career!” But another part of me is thinking, “No. Be sensible. Get a new job in your new town and maybe do a little bit of freelancing on the side.”

I’m torn. Should I make the “big leap” into full time freelancing—or get a normal job and play it safe?

Leap Or Play It Safe?

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Alex says:

Dear LOPIS,

As some who has been a freelancer for the majority of my career—and as someone who has watched numerous friends and clients make the leap from ‘having a job’ to ‘being self employed’—here is what I know for sure:

If you are self-employed, and you feel panicked, frightened, and desperate about booking clients and making money so that you can survive, your clients will sense your desperation—and they will run fleeing in the other direction.

I’m sure—at some point in your life—you’ve encountered a shopkeeper, sales person, coach, consultant, freelancer or entrepreneur who was just a little too pushy.

Maybe it was something about the tone of their website or emails or phone calls. Maybe it was the glaze of fear you detected in their eyes. Maybe they emanated a vague feeling of insecurity. Whatever it was—you could feel it. And it didn’t feel good. You didn’t want to hire that person—and why would you? They’re stressed! Who wants to hang out at a stress ball’s party? Nobody!

Here’s my point:

If diving into full time freelancing—without any “safety net” job to create a feeling of security—is going to turn you into a stressed, sad, panicked person, then don’t do it. Why put yourself through that kind of misery if you don’t have to? Building your freelance practice from a place of “desperation” is not going to bode well for you—and it’s not going to be much fun for the clients you’re trying to woo, either.

Everyone’s financial / lifestyle situation is different, of course. But generally speaking, my recommendation to aspiring freelancers is “don’t quit your day job” until you feel confident that you’ve built up enough of a freelance clientele to support yourself without one.

Imagine chatting with a potential freelance client, making conversation gracefully and joyfully, knowing that regardless of whether they hire you or not, you’ll be fine? That’s a beautiful space to operate from, and ironically, you’ll wind up with more clients if you take that kind of “no stress, pressure-free” approach. So, if possible, try to operate from that place. If that means keeping a part time or full time job for a while longer, to help get into the right emotional space, why not give yourself that gift?

Look at it this way: if having a job helps you feel relaxed about money, so that you can market yourself to freelance clients gracefully and calmly, then your job is a huge check in the “plus” column. It’s not holding you back—it’s helping you!

If you’re going to leap into freelancing, LOPIS, I advise you to make the leap with a happy heart, some savings in the bank to fall back on, if possible, and the confidence of knowing that you’ve already got a small coterie of people who are interested in hiring you. This will give you a self-assured, peaceful attitude… and that attitude will make all the difference.

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Ellen says:

I have been a freelancer most of my life and I must say- I wouldn’t have it any other way. I love the independence, the fact that I am my own boss, and the creative opportunities.

While there are lots of benefits to freelancing, I agree with Alex that it is really important to be financially stable before diving into the freelance world. There is no fun in waking up in a state of panic every day. Make sure you do a budget and figure out all your expenses. Remember you will be paying for everything- including health insurance and self-employment tax- so budget for all of it.

There are also other things to consider before becoming a freelancer. Here are just a few:

Do you have a marketable skill?
In other words are you offering something that people need and that they are willing to pay for. You can have all the passion in the world- but unless you are filling a need, you will not create a financially successful business.

Do you have a large network?
Freelancers who are well connected tend to do the best, financially. But don’t despair if your network is not yet robust. You can begin to build it slowly through social media and also by networking. Go to events in your community. Put yourself out there. Offer free workshops; write articles in the local paper. If you are selling an actual product, get a booth at a Farmer’s Market. There are so many ways to grow your network. It’s just a matter of doing it!

Which leads us to the next important factor.

Do you have the right temperament?
Freelancers need to be self-motivated, comfortable working with many types of people, and open to networking and hustling to get jobs. You won’t get work if you hide in your house all day.

We know this sounds like a LOT to think about. And it is. But in the end, if being a freelancer suits your personality, it is well worth all the hard work.

Good luck!

We’re excited for you, LOPIS as you move to your new town and begin a new chapter of your career.

Let us know how it goes!

Alex & Ellen

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Image: Willie Franklin.

Dear Ellen,

There’s a company I want to work for — it’s literally my dream company in every single possible way — but I have no idea how to get my foot in the door.

Other than the obvious moves, like applying for jobs that they post on their website, what can I do to get hired?

Really Really Really Want To Get Hired

Dear RRRWTGH,

About 15 years ago, I celebrated a major career milestone:

The grand opening of MEarth: a native plant habitat and community garden that I had co-founded and nurtured.

It’s a place where kids and grown-ups could learn how to grow nourishing food, care for the planet, eat well and live well. A HUGE personal dream of mine — finally realized!

My team and I were planning a big party to celebrate the grand opening — a day-long extravaganza to honor our donors and share our vision with the local community.

This party was a BIG deal. And there was just ONE woman I wanted to be there, onstage, speaking to everyone in the room: one of the most famous and sought-after environmental leaders and chefs in the world, Alice Waters.

I knew she’d be tricky to reach, but I simply had to try.

I started by emailing her assistant.

“Would Alice be willing to speak at my event, later this year?”

“She’s insanely busy. Sorry, but no.”

I felt a little deflated — but I didn’t give up.

“Could I circle back to you in a few months, and see if her schedule has opened up?”

“Sure, but don’t hold your breath. Her calendar is just crazy.”

Over the next several months, I slowly and gently built a relationship with Alice’s assistant.

I’d check in periodically, leave a voicemail or two, joke around with him, and offer praise and encouragement for the work he was doing.

I got to know him as a human being.

And one day, he finally gave me the “IN” I’d been waiting for.

“You know,” he said. “If you really want to capture Alice’s heart, send her something in the mail. She loves beautiful things. I can’t promise she’ll come to your event, but whatever you send — I’ll make sure she sees it.”

My heart leapt with hope — and I leapt at the opportunity.

Following his lead, I quickly put together a beautiful packet all about MEarth with photos of the garden, the kids we serve, the crops we grow, the food we made.

I personally thanked Alice in my hand-written letter — praising her as the lead inspiration behind the whole project.

I told her about the upcoming party, and how we were dying to feature her as our keynote speaker.

And I tied the whole thing up with a beautiful bow (literally).

I popped the parcel into the mail, along with a personal ‘thank you’ note for her assistant, as well.

I waited.

And waited.

And waited.

And one day, she called.

Her answer?

“YES.”

Seeing my personal hero take the stage was a peak experience for me — one that I’ll never forget.

Best of all, it revealed three timeless “career lessons” that I’ve carried with me ever since.

If you want to get your foot in the door, get someone to say YES to your request, or unlock a door that seems like it just won’t budge…

1. Be persistent. But be patient.

I didn’t give up after the first “no” — or the second, or the third.

Sometimes, it takes time to get what you want. Don’t get deflated too quickly.

If you are absolutely certain that this is your dream company and you belong there, keep knocking on that door. One day — one way or another — it will open.

2. Befriend the gatekeepers.

I didn’t try to pitch Alice directly. I started by connecting with her “gatekeeper” — her assistant.

I treated him like a human being, not just a faceless entity on the other side of a computer screen. Over time, we forged a genuine friendship.

Whether you are trying to get hired at your dream company or trying to woo a celeb to speak at your event… it’s all about who you know.

Maybe you could begin a friendship with somebody who works at your dream company, RRRWTGH. Someone who could give you the inside scoop on what kinds of positions might be opening up soon, tell you more about the company culture, or even put in a good word for you with their boss. It couldn’t hurt!

3. Go above-and-beyond.

When Alice’s assistant revealed a little “secret” — that Alice loved beautiful things, especially parcels sent in the mail — I paid attention. My snail-mail parcel was visually striking and very “special.” Ultimately, that’s what caught her attention.

Busy people — whether they’re investors, influential writers, or hiring managers who are responsible for fielding hundreds of job applications — get dozens of dull, un-original emails and pitches every day.

When you’re submitting your job application materials, go above-and-beyond the norm. Make a video. Create a comic strip panel. Include impressive testimonials. Tell a powerful story. Show your humanity and uniqueness.

A little originality can go a long way.

You’re clearly passionate, resourceful and self-motivated, RRRWTGH, so I know you’ve got what it takes to get your foot in the door at this company — or any company you choose.

Do me a favor: write to me when you land your dream job.

I’ve got a feeling it might happen a lot sooner than you think…

Find great work. Do great work. Unlock every door in your way.

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Image: Willie Franklin

Dear Ellen,

I recently applied for a job I really wanted. I got pretty far along in the interview process and it seemed like they liked me and wanted to hire me.

I was starting to get really excited. Then, after weeks of waiting, they emailed to tell me that I hadn’t been selected.

They were very professional and polite, of course, but I still feel so upset. I know I should just “get over it” and apply for something else, but I don’t feel like I can handle the disappointment all over again.

Any wise words of advice to help me get back in the saddle, so to speak?

Majorly Unmotivated

Dear Majorly Unmotivated,

We’ve all been there: slogging through a terrible, no-good day. (Or week. Or year.)

Maybe you awkwardly fumbled through an interview for your dream job.

Maybe you froze up in the middle of a presentation — scrambling for your notes, sweating bullets, silently cursing Power Point.

Or maybe you did everything “right” — you gave one hundred percent, your absolute best — but you still didn’t get chosen for the opportunity you wanted.

It’s rough. I know.

But guess what? If you feel like a “failure,” you’re in very good company.

Just think about JK Rowling, who received 12 rejections before one publisher said “Yes!” to Harry Potter.

Or Oprah, who got fired from one of her first TV news anchor positions for being “too emotionally involved in the stories.”

Or Thomas Edison, who made one thousand faulty light bulb prototypes before he finally got it right.

No doubt about it: I’ve had my share of failure and rejection, too.

In fact, there’s one particularly terrible, no-good day that will be forever burned into my mind — from back when I was the Director of a non-profit called MEarth, a terrible, no-good day that changed my life, for the better.

And here’s how it happened:

At MEarth, my team had a big dream — to create a community garden and educational center for children — but we had several obstacles in our path.

Our biggest hurdle? We needed the local School Board’s approval before we could move forward. And they were not easy to impress.

We worked hard to prepare our presentation — and we thought we had our ducks in a row.

But once we walked into that School Board meeting, it became obvious that there had been a major miscommunication between the Superintendent and the Board. They’d been given the wrong information about our project — and after a frustrating hour-long debate, we walked away empty-handed.

The next morning, my team and I sat around our conference table, sadly bemoaning what could have been.

As the project leader, I felt more wounded and humiliated than anyone. But I was unwilling to let our dream just fizzle away after one disappointment.

I told the group, “We’re going back in. We’re not taking no for an answer.”

Everyone knew our chances were slim. We were going to present the same idea to the same group of people — who had already firmly rejected it.

But we knew that our project was important — that it would help hundreds of children, every year. And we also knew that a story — told the right way — could change everything.

We went back in. We re-told our story to the Board, took responsibility for the past confusion, showed them our passion and won the day!

It was a major turning point for our scrappy little organization and a major life lesson for me.

I realized that there’s only one way to bounce back after a terrible, no-good day.

It takes courage, but it’s not complicated:

You simply decide to go back in.

Don’t let a small bump in the road — or even a thousand bumps in the road — derail you from your dream.

When you feel humiliated, depressed or just plain defeated, remember what you’re fighting for. Remember who you are.

Remember, too, that rejection is just part of the process of being alive, building a career, putting yourself out there, or doing anything worthwhile. It may sting temporarily but the pain will always subside as long as you keep moving forward. The only thing that will really hurt you, permanently, is giving up on your dream.

You can do this.

Saddle up.

Go back in.

Find great work. Do great work. Unlock every door in your way.

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Image: Willie Franklin

Dear Ellen,

I have worked a a lot of different jobs and I must say, none of them have made me happy. Yet, when I try to find a new career path, I get overwhelmed. There is just too much to choose from.

I have lots of interests and I’d like to do work that makes a difference in people’s lives. Yet, every time I make a choice, I second guess myself and wonder if I might be happier at a different company, or doing a totally different career?

How do I narrow down my choices and figure out what the right career path is for me?

Signed,

Too Many Choices

Dear TMC,

For women in my mother’s generation, career options were fairly limited.

You could become a secretary, a nurse, a school teacher, or marry a man from your hometown, end your career and start a family. If you weren’t excited about any of those options, you were a bit out of luck. Only the exceptionally brave got to break the mold, and even for them, the road was long and tough.

We’ve come a long way since then—thank goodness. As women, we have more career choices than ever before.

Just hop online, and whoosh! Millions of available jobs are open to you. Male, female, doesn’t matter. You’ve got options and you can go ahead, fill out a form, and apply. Things certainly aren’t “perfect,” but very few doors are firmly “locked” anymore.

Everything is a possibility.

So if we’ve got more career options than ever before (CEO, life coach, ballerina, financial planner, physician, astronaut, author, all of the above!) why do multiple studies show that women are less happy now than they were 40 years ago? Things should be getting better, right? What’s going on here?

The answer to that question is complex, and probably can’t be summed up in a single blog post, but part of our collective dissatisfaction may have to do with something called “the Paradox of Choice.”

Never heard that term before? Here’s a quick intro:

In a now-legendary study on “choice”, conducted by psychologists Sheena Iyengar and Mark Lepper in 2000, the researchers set up a jam tasting station at an upscale food market and offered free samples to passing customers.

When they offered customers 24 varieties of jam, customers initially seemed eager to stop by for samples (“Sure, I’ll try some! Yum!”) but when it came down to choosing their favorite jam, purchasing it, and taking it home, these customers really struggled. They felt paralyzed by all the choices on the table and just couldn’t decide. Most walked away empty-handed.

In contrast, customers who got offered just 6 types of jam were 10 times more likely to choose a jam, buy it, and take it home than the people who were faced with 24 possibilities.

This phenomenon became known as “The Paradox of Choice.”

As this study shows, more choices seems like it should be “better,” but maybe “excessive choice” is not as great as we think. Maybe having more choices just paralyzes us, causing us to hover over the jam table of life, worrying that we’re making the wrong jam investment or that, maybe, there’s an even better jam out there, at a different store, which we might be missing out on!

Just replace the word “jam” with “job,” and you can see how this same paradox can create major tension, unrest, and dissatisfaction within your career.

But, Too Many Choices, this does not mean you are doomed to a life of perpetual torment and dissatisfaction. You don’t have to live like that.

Why?

Because even though having tons of choices can be paralyzing, there is one simple choice that can dissolve a lot of that choice-induced stress.

You can simply choose… to be happy.

Now. Later. In any moment, job, or circumstance. No matter what.

You can…

• Choose to see the bright side of things.

• Choose to feel grateful instead of resentful.

• Choose to enjoy your daily routine even if it’s not perfect.

• Choose to find your boss’ antics humorous instead of annoying.

• Choose to focus on the task at hand—the job or career you’ve currently got—rather than constantly drifting off into la-la land wondering, “I wonder if I’d be happier at a different company doing XYZ…”

I’m not saying, “Stop dreaming” or “Stop searching for ways to upgrade your life.” Not at all. But even if you’re in the middle of an epic quest to find the perfect jam (er, I mean, job) you can choose, in each new moment, to feel excitement… to feel awe… to feel gratitude… even joy.

You can take a deep breath and say to yourself:

“It’s tough to choose because I’ve got so many amazing options. But no matter which one I choose, I can’t choose ‘wrong’. No matter which one I choose, I will be happy. Because happiness is a choice that I make, not a ‘gift’ that a company or a job title gives me. It’s my choice and I can keep choosing it, anytime, anywhere.”

So TMC, choose happiness. The right job will certainly follow.

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Image: Willie Franklin

I love giving advice. So does my friend Alex. 

We come from different generations and we’re at very different points in our lives and careers. But we share the same philosophy: every door can be unlocked. 

Every once in a while, we  partner up on a special installment of my advice column, Ask Ellen. It’s called… Ask Alex & Ellen. 

Two hits of advice in one column. 

We hope you enjoy it!

Dear Alex & Ellen,

I have philosophical question for you (hope that’s OK!)

All throughout my 20’s, I worked part-time as a barista at Starbucks.

Most people would think of that as a “lame” job, but I really loved it. I got to know the local customers, I knew their names (and their kids’ names), I remembered their favorite orders, and a bunch of them brought me presents to celebrate my graduation from college.

All I was doing was steaming milk and slinging espresso, but to me, it was meaningful. I felt like I was part of a community.

Fast forward to today: I’ve got a “real” job working for a non-profit, supposedly “saving the world.” But I just stare at a computer screen in my cubicle all day — and I don’t feel “connected” to my work. In many ways, I miss the simplicity of my barista days — chatting with people face to face, knowing I was serving them something delicious and making their day a little better!

So my big question is:

What is a “meaningful” career, anyway?

And also:

Do you think I should quit my job and start working at Starbucks again? (Just kidding. Except, not really.)

Signed,

Total Existential Crisis

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Ellen says:

Dear TEC,

Young people are often told that they have to “change the world.”

Pursue big, fancy careers. Collect hefty paychecks. Do notable, newsworthy things. Be a “hero.” Be a “leader.” Be a “revolutionary.” Make “history.”

But the world can’t run on “revolutionary history-making leaders,” alone.

We also need cupcake bakers, holiday gift-wrappers, hedge-trimmers, bartenders and B&B owners.

You might not (literally) want to work at Starbucks for the rest of your life, but there’s clearly “something” about that position that made you feel happy and fulfilled. Whatever that “something” is, that’s worth exploring and carrying into your next job or career — whatever that may be!

If I had to guess, I’d say that you’re the kind of person who thrives on conversation, community, and connections. You’re good at making people feel at home. Making beautiful things that brighten people’s days. That’s great!

Instead of working at Starbucks, you could take those skills and …

– Open your own cafe, bakery (like these gals!), coffee shop, or catering company.

– Work for a cool company that focuses on food (like this one), pleasure, community, gift-giving  or connection ( this company is so lovely!).

– Open a small “home-based business” where you know all of your customers on a first-name basis (like a dog grooming business, a childcare service, massage therapy, something like that). These days, you can even cook and invite friendly strangers over to your place to eat dinner… for a fee, just like a restaurant! (Think: AirBnB but for foodies.)

– Or, keep your current job (or a similar cubicle job) but open a “side business” where you can indulge in work that feels exceptionally meaningful and fun, even if it doesn’t make you tons of money at first. In time, who knows? Your “side hustle” could blossom into your full time gig!

My point here is that “success” doesn’t always come in a “conventional package.” It’s not always about having the corner office, the hefty paycheck, the benefits package, or the “fancy” job title that makes others feel “impressed.”

Success comes in every shape, flavor and form.

Just like you can customize your latte at your local Starbucks (three shots, half sugar, light on the foam, tall, extra hot) you can customize your career so that it’s absolutely dreamy for YOU.

This is your LIFE, after all… and it’s just too darn shot to sip on something that doesn’t taste right.

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Alex says:

Dear TEC,

I have an Annual Existential Crisis (I’m overdue for mine this year – guess that means it’s coming up, soon! ha!) so I can completely relate to your angst.

Like you, TEC, I often feel torn between my desire to lead a simple, cheerful life and my desire to “make a difference” in the world.

Much like Ellen, here’s what I’ve come to realize:

“Making a difference” can take many forms.

If you want to make a positive imprint in another human being’s life, you can do that with one email or handwritten note… with one cupcake, baked with love … one history-making speech from a podium in front of the White House… or four simple words whispered to a friend in need: “I believe in you.”

You see, changing someone’s life for the better isn’t always a big, brazen, flashy affair. Often, it’s a very quiet moment, witnessed by only two people, not millions.

So, to all the baristas, bakers, candlestick makers, pre-school teachers, house cleaners, and other people who are working tireless without much fanfare or celebration: you matter, too.

Because you enhance and upgrade people’s lives in so many ways. You are “changing the world,” too, even if you never see your name emblazoned on a plaque in front of city hall.

I suppose I should give you some specific advice, TEC. Here goes…

I vote:

Go ahead and get a job back at Starbucks slinging espresso, if that truly makes you happy. (Or happy… for now!)

Hell, I am writing these words from my local Starbucks right now! It’s practically my second home, I visit every day, and the baristas greet me by name. They always make me feel welcome and I’ve done some of my best work here. My local ‘bucks baristas are consistently enhancing my life… and hundreds of others. I have nothing but the highest esteem for Starbucks baristas!

Every smile, every embrace, every kind word, and good, strong cup of coffee makes a difference in this challenging world.

So, go right ahead:

Change the world in your own quiet way.

And don’t let anybody tell you it’s “wrong.”

Kindness, generosity, passion, artistry, in any form, is never wrong.

Alex & Ellen

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Image: Willie Franklin.

Dear Ellen,

So… I wasn’t exactly the world’s most responsible teenager. In fact, I was kind of a train wreck.

I totaled my car once. I drank while I was underage. I got into fights. My grades were passable, but not stellar.

Now — after attending college in another city and “growing up,” a lot — I’m living back at home with my parents and trying to kick-start my career.

I majored in Physiology with a minor in Nutrition and I’m also a certified personal trainer. I want to get my fitness training and health coaching business off the ground.

Problem is, my parents — and everybody else around here in my hometown — still perceive me as the irresponsible teenager I used to be, not the adult I am today.

I’m really struggling to change people’s perceptions. It feels like everyone is frozen in the past.

Should I just give up, move to a bigger city where nobody knows me, and start over?

Or is there some “secret” to convincing people that they can trust you?

Signed,

Bad Reputation

Dear BR,

As I see it, there’s no “right” or “wrong” choice here.

Whether you remain in your hometown or move on to a brand new city, you are going to face a big challenge:

Starting from “zero,” building up a following of clients, and establishing a strong reputation as someone who is reliable and excellent at their work.

In your small town, you’ve got an additional challenge: changing old perceptions.

But you’ve also got an additional advantage: a great story!

You can play up the fact that you used to be a reckless teen, but building discipline and focus through fitness changed your life.

Now, look at you! You’re a driven young entrepreneur. Not just another run-of-the-mill personal trainer: you’re a role model for other teens and grown ups, alike.
You are a living example of how getting serious about fitness can transform your whole life, not just your body.

Bottom line? Instead of downplaying your past or trying to make people “forget” about your rocky teen years, I say: do just the opposite. Talk about it. Bring it up. Use your “before + after” storyline to create even more momentum for your new business.

If you’re feeling skeptical that this approach can work, may I remind you about…

Tony Robbins – He’s the most famous motivational speaker in the world, making millions through his “self help” programs. Why? Because he started out as a broke, hopeless janitor and then reinvented his life. People love his “turnaround” story — it’s the main reason why he’s able to connect with audiences so powerfully!

Robert Downey Jr. – He’s one of the most talented and beloved actors of our time, but his rough childhood sent him into a spiral of drug addiction that landed him in jail — and almost ended his life. He fought hard to get sober and reclaim his floundering career. The result? Audiences cheer for him, not just because he’s a terrific performer, but because of what he had to overcome just to survive.

Angelina Jolie – Before she became a filmmaker, humanitarian, and United Nations ambassador, Angie was a pretty twisted sister! Like Downey, she dealt with drug addiction in her youth, had a fondness for the “darker” side of life, and reportedly kept photos of corpses in her home (uh… love you, Ms. Jolie, but that’s super creepy.) Today, she’s profoundly respected. She was the first-ever recipient of the UN “Citizen of the World Award.” (Bill Clinton, another icon who recovered from crushing public scandal, received the same award… 4 years later!)

Just goes to show…

Your “rocky past” story can hinder you — or it can catapult you into success.

It all depends on how you choose to tell it.

Just like Don Draper from Mad Men often says, you can’t let other people gossip and whisper and control the conversation about you. You’ve got to take charge.
You’ve got to “change the conversation.”

Do that, BR, and I have no doubt that you will be successful in your hometown, in a new city, or anywhere you choose to go.

I always love a good “underdog” story and you can bet: I’m rooting for you!

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Image: Willie Franklin