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6 Tips For Navigating Your Role As An Entrepreneur

6 Tips For Navigating Your Role As An Entrepreneur

On August 17 I went to the YC Alumni demo day in Mountain View. As the class of Summer 2015 proudly pitched their ideas in perfectly rehearsed two and half minute pitches, my multitasking mind thought about how much time has passed since Vasco Pedro, my fellow co-founder and CEO, presented Unbabel on that same stage in March 2014. It felt like eternity. I began to think further back to my first startup, a total disaster that left me penniless in 2012, then to when I quit my job to start a female beauty company that never made off the paper, and to my first job in tech in 2005. It’s been 10 years since I embarked on my journey in this crazy world of startups, technology, subscriptions, and hyper growth, and became an entrepreneur.

Being an entrepreneur is a difficult job that we’ve all chosen for different reasons, but the underlying motivation is our passion for ideas that we believe in so much that we’re willing to do what it takes to make them come to life. After having worked with startups around the world, I’ve gathered enough experience to last me a lifetime. Here are my top six tips for navigating your role as an entrepreneur.

Know your self worth

It’s easy to confuse your self worth with the growth rate of your company, how much money you raised, or how many times you heard the word “no” this week. After co-founding ActualSun, the team imploded and we failed to build a product, lost our pilot customer, and the trust of our investors. I thought I failed as a manager and as a person. Looking back I realize it was just a bruised ego and allowing myself to think that way only made it harder to get back on the horse and try again. Building a company is a 24/7 job and it’s natural to obsess about what’s going on with your startup. Thoughts are constantly swirling through your head about how to grow, who your customers are, how to sell, who to sell too, how your ideas stand out, and how to communicate them in a meaningful way. When you spend so much time thinking about something, you begin to identify personally with it. It stops being your company and starts being you.

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But it’s not. You’re a worthy, unique, valuable human being just because you are you. There is no point in identifying yourself too much with your failures or successes. If you get down when the business is down, it’s much harder to turn it around and you might fail to see the window that opens when that door is slammed in your face. Balancing your reactions to the ups and downs of your business is all about remaining confident in the face of failure and maintaining modesty in your success.

Keep calm and try again

If you ever met me in person you’ll see “Keep Calm and Try Again” is actually my phone’s screensaver. As entrepreneurs we naturally see ourselves as leaders and are always striving to succeed. Our desire to be the best often causes us to go into a bit of a panic when things don’t work out the way we had hoped. A large majority of the things we work on will fail and on multiple levels; weer that’s your campaigns, channels, customers you go after, or people you hire. You will make mistakes and lots of them, but that just means you’re making decisions and taking chances.

In a way, it’s like A/B testing everything. I first started getting used to trying things when I worked for TIMWE. We did a lot of online ads, and had tons of different landing pages. We would test if a particular piece of content would sell, a new affiliate network, or a new banner design. It sounds basic, but this was in 2006 before Unbounce and Optimizely made it easy, we were running these experiments manually. The marketing team discussed our experiments as a group on Monday mornings and if it worked we’d do more, if not, we’d try something else. You can apply that to literally everything! Remember, each attempt is a learning opportunity, a teachable moment. The silver lining of any failure, is what you learn as a result. A friend of mine summarized it perfectly by saying, “Learning is what you get when you don’t get what you want.” I love that sentence and always look for what I learned in each project. If you can take your failure and turn it into an opportunity for growth, you and your company will be able to turn failures into success.

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Become a well rounded person

Even though you might feel like you don’t have enough hours in the day, taking time away from work to hone different interests, hobbies, and passions is good for business. Aside from it being a good stress release, it makes you a richer and more well-rounded person and opens you up to meeting people with different opinions, skills, and experiences than you. All my YC batch mates (Go Winter 14!) have some kind of interest that helps take their mind off work and do things with different people. They participate in a range of activities from stand up comedy, paragliding, and team sports, to climbing mountains, camping, building cities in the desert, and cooking. And me? I did my first triathlon on August 23!

The beauty of adding more dimensions to your life is that it will actually make you a better founder. Here’s a secret, as an entrepreneur you’re always selling the vision, the technology, the company, to investors, customers, employees, family, and friends. Selling is all you do, and it’s much easier to sell if you can create rapport with people around other things you might have in common aside from your company.

Remember you’re not alone

I hear these phrases time and again, “most startups are shit-shows”, “there is always something broken”, “the problems are just different when you grow”, “as a CEO I focus on the part of the company that is under performing the most and fix it.” Every step of the way, from idea to IPO, hell is always about to break loose and something that might kill your company is always about to happen. Not only do we all have some type of problem to solve, we all think we’re the only ones. We’re not, everyone goes through the struggles of building their business.

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I have a group of startup friends I have dinner with once a month just to talk about the companies we are building in a friendly supportive environment (with good food and wine). Find your peers, start a group, get together regularly, and talk it out. Just sharing dilemmas out loud is often half the solution, and as an added bonus, you say them to a room full of other entrepreneurs who can draw on their experiences and offer advice.

Practice your people skills

Dealing with other people is hard, and it’s crucial that you learn to be great at it. Find ways to make people do what you want even when you don’t have hierarchical power over them. No, I don’t mean be manipulative. What I mean is, make people want to work for you. Learn what interests the people you work with, how they want to expand their skill sets, and how you can help them. Knowing these are critical for a successful business.

There’s a new contract between companies and people. In the old days people were resources who gave themselves to companies in exchange for predictability, security, and a job for life. Today, that type of employment is a distant memory. There’s no predictability anymore, so instead of searching for jobs that can provide security, people want jobs that offer them the opportunity to learn, better themselves, and work in a variety of capacities. It’s your job to create those opportunities for them and to make sure your team is naturally aligned with where you’re going and want to be with you for the ride.

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Respect your co-founders

The way you communicate with your co-founders sets the tone for your whole company. You and your team of founders are the backbone of your startup and set the company-wide example of how to be team players. When business gets stressful, your co-founders are your support system and are just as invested in the success of the company as you are. Always assume they are doing the best they can and working as hard as they can. You didn’t choose each other randomly, it was a conscious choice to go into business with one another and when times get tough, it’s important to remember that they are invested and deserve your respect.

It’s equally important to never let doubts or unspoken pain fester. Everyone is human and falls prey to outbursts that come across as disrespectful. At Unbabel we call that emotional debt, and unlike technical or sales debt, this isn’t the kind of debt that you can afford to pay back later. A startup is like a relationship and when doubts and resentment begin to build up, they are bound to surface in the throes of another issue. So don’t let it build up and have the tough conversations about your stress, fears, and needs, and listen to those of your founders and your team. Make sure to find ways to make everyone feel valued and part of the team. As a way to avoid a build-up of emotional debt, take company trips and do something fun to build a strong connection between each member of the team.

These tips are helpful for every entrepreneur who wants to navigate successfully through the minefield of living the startup life. Implementing these key strategies will help you develop yourself personally by having a grounded sense of yourself and becoming more well-rounded and empathetic. You’ll grow your business by remaining calm in the face of failure and looking for the next opportunities. Finally, you’ll be better equipped to nurture your team by removing emotional debt and promoting an environment of mutual respect. If all else fails, listen to your gut and remember that you catch more flies with honey than you do with vinegar.

Featured photo credit: Navigator/ Thomas Abbs via flickr.com

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Last Updated on August 14, 2020

How to Find a Career That Is Right For You

How to Find a Career That Is Right For You

There are thousands of careers to choose from. No wonder finding the one that’s right for you can feel like a guessing game.

Choosing or changing careers can be scary. Even if it’s right for you now, you might wonder, who says it’ll still be a fit in the future?

The truth is, you have to start somewhere. Whether you’re looking for a first job out of college or need a new career, follow this process to find the right one for you:

1. List Out Careers You Could Pursue

It sounds simple, but it’s good advice: Start with what you like. Even before you begin looking for the right career, you probably have an idea of what you’re interested in.

Next, make a second list, this one including your strengths. If you aren’t sure whether you’re actually good at something, ask someone close to you who’ll give you a truthful answer.

Once your lists are made, cross-reference them: What do you like to do and do well?

In a third list, rank these. If you’re skilled at something you don’t particularly like, for instance, that should fall lower on the list.

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2. Take a Career Assessment

Standardized tests shouldn’t make decisions for you, but they can get you pointed in the right direction. Career assessment tests gauge your abilities and interests and make recommendations for career paths based on the answers you give.[1]

Before reviewing your results, take a break. Getting some perspective can help you see whether your answers were guided by your mood. Look at the percentage match and ask yourself whether you could see yourself doing the work of the career or role every day.

For example, if your responses emphasized helping others, the test might point you to a medical career. However, if you don’t want to work in a hospital or clinical environment, you might cut that option or place it lower on your list.

3. Sweat the Details

Every career has gratifying and frustrating things about it. Before you choose one, you need to be clear on those. Reading reviews and job descriptions you find related to each career, make a list of its pros and cons.

There are a lot of factors to think through. Key questions to ask yourself include:

  • What are the hours required by this type of work? Can they be flexible?
  • What skills are required? Do I possess them, or would I be willing to learn them?
  • What are the education requirements? Can I afford to go back to school?
  • How much do jobs in the field pay? Is the payscale top-heavy or evenly distributed?
  • What does job growth in this sector look like? Are they traditional or contracted roles?
  • Are opportunities in the field available in my area? If not, would I be willing to move?
  • Would I be working solo or on a team?

In answering these questions, you’ll find yourself crossing a lot of careers off your list. Remember, that’s a good thing: You’d rather find out a career isn’t right for you now than after you’ve put yourself on that path.

4. Find the Sweet Spot

The crux of the career question is this: What’s the “sweet spot” between your interests and strengths and the market’s needs? The greater the overlap, the better.

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Be warned that you’ll have to compromise. Perhaps you enjoy working with animals, but there’s no demand for that line of work in your area. You might be good at math, but you wouldn’t want to crunch numbers in a cubicle for a living. Finding balance is crucial.

5. Start Networking

What’s the best way to get the real story about the careers you’re interested in? Talking to professionals in the field.

Where should you find these people?

  • Reach out to local businesses.
  • Scour your social media networks, particularly LinkedIn.
  • Ask a past employer for recommendations.
  • Sign up for industry events and conferences.

Schedule a short interview with each of your new connections. Ask them to weigh in on the comments you see online. Every role and company is a bit different, so don’t be surprised if their responses don’t align.

Regardless of who you find or what they say, write it down. If one interviewee’s responses differ wildly from online responses, chat with someone else in the field. Do your best to find out what’s the rule and what’s the exception.

6. Shadow and Volunteer

As valuable as networking can be, you need a firsthand glimpse of the work. If you hit it off with one of your interviewees, ask to do some job shadowing. Sitting beside someone as they work can help you understand not just the pay and the responsibilities but also the culture and work environment associated with each career.

Job shadowing is a good way to get your feet wet before taking a career plunge. If you felt uninterested or unhappy during your shadowing experience, it’s a good sign that you should ponder a different career path. If your shadowing experience made you want to come back for more, you may have found your calling.

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Volunteer work is an alternative to job shadowing that can get you the experience you need as you analyze your career options. As a volunteer, you can be more flexible with your time and get opportunities you wouldn’t find elsewhere.

7. Sign Up for Classes

Many careers have an academic component that you can’t ignore. If you decide you want to be a lawyer, for instance, you might want to know you can survive law school first.

Sign up for an introductory class or two related to each career you’re interested in. The earlier you do this, the better. If you’re still in college, the class will count as an elective and may be covered by your scholarship, but if not, look for a community college option to keep costs low.

Taking a single class is not the same as earning a degree in the field. With that said, it’s a good way to test the waters before you invest thousands of dollars.

If the content interests you and you look forward to class each week, that’s a good sign. If you start dreading the class or choose to drop it, focus your attention elsewhere.

8. Enter the Gig Economy

Contracted work is a great “try it before you buy it” career tactic. Skipping to an entry-level role requires more commitment than you might want to give while you’re still investigating your options. The gig economy offers the best of both worlds: paid work as well as flexibility.[2]

Gig workers take work from companies or individuals that do not directly employ them. Plumbers and artists are good examples. Rather than receiving a regular paycheck, they sell their services by the task or deliverable.

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In the gig economy, you aren’t bound by long-term agreements. If you don’t like the experience, you can simply move on.

You never know if you’ll enjoy something until you try it. And because contractors work with professionals in the field, gig workers naturally get networking and shadowing opportunities.

9. Market Yourself

As you zero in on your dream career, there’s one final test you can use to find out whether you’ll be successful: marketing yourself as a candidate for hire. Whether you get bites is a key indicator of how you’ll fare in the field.

Beware that, as someone without much experience in the field, you’re going to get a lot of rejections. Don’t be discouraged. If you get two interviews out of 50 applications, think of it as two opportunities you didn’t have before to find your ideal career.

Just as important as outreach is a good inbound strategy. Set up a website, and post your portfolio on it. Describe your dream job on your social media.

Recruiters are constantly on the lookout for candidates that fit their company. The more exposure you get, the more people will be interested in what you have to offer. Put yourself out there, and you just might find the perfect fit.

Don’t Give Up!

Nobody ever said it was easy to find a career that’s right for you. Finding one is tough enough, and even then, you may find yourself looking for a new field ten years into your career.

Whatever you want from your professional life, you have to be willing to put in the time. Don’t hesitate, and don’t give up. Start your search today.

More Tips on How to Find a Career

Featured photo credit: Saulo Mohana via unsplash.com

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