An Expectation Hangover, an Awful Job and a Master’s Thesis

Key Takeaways

• Find and nurture a lifeline to cheer you on and pick you up.
• Leave room in your 2021 plan to adjust and pivot.
• Wanting to quit along your journey is completely normal.

Yet, finding fulfilling work that would lead to a long-term career was filled with moments of uncertainty, doubt and yes, a pounding expectation hangover.

"I graduated from the University of Oregon in 2009 during one of the worst recessions in modern history, with a degree in education and zero job prospects," McGoodwin shares. "I did everything right. I networked, attended every career fair – the equation in my head said I should be doing exciting, engaging work after graduation. The tough reality is that you can do everything right and the world does not hand you your next opportunity on a platter."

"I’m a Millennial. I was raised to believe that women can do it all. Hundreds of studies of our ‘on-demand’ generation show that Millennials have many stellar qualities; however, patience is not one of them," McGoodwin says. "I watched my female role models on TV become doctors, lawyers and businesswomen. That was not happening for me."

McGoodwin moved from Oregon to Los Angeles with the hope that a larger city would offer more job opportunities. "I was wrong about that," she says. "I did finally get a job as an administrative assistant, in the dental school of a large university. I was thankful for that job because it meant I was working, but I had to cover the clock on my computer because time went by so slowly." McGoodwin says she reached her "lowest of lows" when she was asked to feed paper into a printer ONE. SHEET. AT. A. TIME.

Things started to improve for McGoodwin after this low point – but it wasn’t just a lucky break. "I intentionally changed my entire approach to work and my career. It was not easy – frankly, it was a lot of work," McGoodwin said. "I started by forgiving myself for not having things all figured out. I stopped looking for the ‘perfect job’ and concentrated on small, intentional moves instead." One of those moves was to volunteer for an assignment in university recruiting. McGoodwin enjoyed the work – so much so, that she stopped watching the clock at work.

McGoodwin eventually pivoted to a job in university recruitment at Hulu, at the time a start-up company of its own. She noticed immediately that there were not a lot of women on staff – so few, in fact, they did not yet have a maternity leave policy.

"I learned a lot at Hulu, including what it takes to get a start-up off the ground. Start-ups are a tremendous amount of work, sometimes without a lot of definition at first. It was like going back to school for me," said McGoodwin. At the same time McGoodwin was working on her master’s degree in communication management, which required a final thesis. Given the opportunity to pick her topic of study – and inspired by her own non-linear career journey – she chose "Millennial women and career resources." Career Contessa was the prototype that resulted from McGoodwin’s master’s thesis research and conclusions. "It was before Sheryl Sandberg’s Lean In book and foundation were launched. There was no online media platform, or resource, dedicated to providing women the very same career help that I needed."

When She Jumps, It’s Headfirst

Always intrigued by start-up companies, their leaders, cultures and growth trajectories, McGoodwin had been working to bring Career Contessa to life while she still held her full-time job at Hulu.

"The first year in business is like boot camp. It’s a rite of passage – like living in a dorm. You are getting your bearings, establishing your footing. When it’s over you don’t necessarily want to go through that again," McGoodwin comments. Career Contessa started as a blog with additional webinar content. An audience started to build slowly but surely. "I developed a lot of content the first year, which started giving the business a presence and a voice. It was a natural segue from recruiter, to giving advice to those who needed and asked for it. Looking back, I wasn’t overly thoughtful about Career Contessa’s offerings and revenue streams that first year," she shared.

McGoodwin’s "I’m all in" decision came as she listened to a panel of women entrepreneurs at SXSW in 2014. The question posed to the panel was, "If you could change one thing about starting your business, what would it be?" "Every one of the panelists said they would have started their business sooner," said McGoodwin. "At that moment I was all in. I flew home, resigned from my job at Hulu, and put all my energy into Career Contessa."

"In year two I worked on monetizing my advice, developing brand partnerships and further defining our service offerings. If I wanted Career Contessa to be a comprehensive resource, what would that look like?" McGoodwin said. "I created a revenue stream by writing articles for other news sources. I continued to ask questions of everyone I met. ‘How are you making this work? What are your revenue streams?’ You can learn so much from a single conversation."

Growth of the platform continued over the next several years, building followers along the way. Some years have been more growth-oriented than others. Career Contessa now features online courses, coaching access, a job board, webinar content, eGuides, quizzes and templates. Topics cover a wide variety of career advice, from managing up and creating impactful presentations, to responding to microaggressions at work and how to answer COVID questions in an interview, and more. The content is timely, easy to navigate and useful, not only for Millennials, but for all women in business. Followers are only one measure of success, but Career Contessa now communicates to an audience of more than 3 million each year.

Made of Glue, Not Glitter

"This year with COVID, many small- and medium-size businesses had to quickly pivot to what I call ‘survive not thrive’ mode. Even the best laid plans were annihilated," McGoodwin commented.

It’s difficult to find a silver lining in the uncertainty of COVID-19, but McGoodwin offers that it forced her and other business owners to focus on areas of their businesses that were on the back burner. "I applaud all owners who ‘got scrappy’ and figured out how to make things work." She refers to businesses who built retail websites in a week, those that quickly developed content to help people cope and others that overhauled their digital outreach approach.

According to McGoodwin, March and April 2020 brought Career Contessa back to basics. "We are a business. We need to make more money than we spend. For us that meant taking a hard look at expenses, revenue streams and headcount, and unfortunately, like many others, we had some layoffs," McGoodwin comments.

"Good things have come out of this. It forced us to pay attention to holes in our business that we needed to fix now, rather than later. We prioritized multiple billable revenue streams and now we are stronger – we know now that we are made of glue and not glitter," McGoodwin says.

Purposeful Planning for 2021

"In 2021, our approach will likely be ‘less is more,’" says McGoodwin. "We want to be purposeful with our calendars and set aside time to adapt to whatever comes our way. Overplanning for 2021 seems a bit silly right now, during this period of uncertainty. We will continue to bolster our offerings that best support multiple revenue streams, which will make us even stronger."

"Careers are always changing, and it is the role of Career Contessa to stay on top of these trends," McGoodwin comments. "We will leave time on our 2021 calendars to adapt, learn and bring new information to our followers."

Advice for Women Entrepreneurs and Executives

"I have the best job – I get to spend each day talking to women and see what’s working for them," McGoodwin says. The advice and approach she’s identified over the years is featured in Power Moves, her first compilation of advice and methodology for guiding careers for Millennials and beyond. Below are a few nuggets of wisdom, with many more to be found at CareerContessa.com.

• Find and nurture a lifeline (or two). One of the best things you can do is find a confidant, a friend, who is willing to be part sideline cheerleader and part business advisor. You, in return, will be theirs. Set up regular times to talk, and keep those dates. Sometimes when you are frustrated you just need to hear another voice (beside the one in your head).
• Wanting to quit or give up is totally normal. We are all human, not robots. Feelings of frustration or hopelessness along an entrepreneurial or career journey are normal and should be recognized as so. There are things that all of us do not want to do at work. Address processes or work habits that tend to make your day more difficult. Achieving a series of small successes is a confidence building habit.
• Recognize that careers are not "on-demand." The consumer part of you gets what you want when you want it. The professional side of life does not work the same way. If you are counting on a linear career trajectory to an ideal job, you will most likely become frustrated and anxious. Refocus on progress – on the journey – not the myth of perfection or the "dream" job. Focus instead on what is real and currently in front of you.
• Entrepreneurs should prioritize billable revenue streams. In the era of COVID and beyond, your business will be stronger with multiple revenue streams. There will be other years when business owners will have time for ancillary projects. Work on the "glue," not the "glitter."
• Prioritize mental self-care/well-being. Everyone needs downtime – we are people, not machines. It’s easy to get into the "badge of busyness" rut and not find an easy way out. One habit that helps is to look at your calendar in weeks, not days. It’s easier to find time for a chat with a friend, or an hour to read or watch TV, if you look at the week and determine where self-care fits in.

The Support You Need

For more Key4Women^® resources to help you reach your goals, visit key.com/women, or email us to learn more.

For more information about Lauren and Career Contessa, visit CareerContessa.com.