My Career Path and Advice for Career Junctures

From Hotjobs.com to the Wilderness

Hi guys, 

As someone who’s become very successful, but only through a lot of uncertainty and back-breaking work, I want to share with you my own career path and my journey.

I’ve learned a lot from the successful people who mentored me, but unfortunately even more from years of unnecessary mistakes. Now I mentor young people and mid-career professionals and my hope is always that I can distill my own learnings to them so crisply that I save them years and years of time and painful mistakes, and give them a shortcut to success. Turn the lights on in the room and help get them on the quickest and most enjoyable path to wherever they are trying to go.

My career path has been hard and at times really ambiguous, not clear where I was headed. This is very common, and I’ll show you how to set your compass so you avoid unnecessary headaches and meandering.

My career is a good example of “things are going to happen in the only way that they can happen.” And I don't mean that in terms of fate. I don't think that our lives are fated. I mean it in terms of time — it takes time for things to come together. You've got to learn your lessons and take your punches. You've got to just be patient and trust that in the fullness of time, the small things are going to heap up to great things, and life is going to deliver for you.

I’ll start at the beginning. I was born in St. Louis, Missouri. I'm the second oldest of four kids. We had a very stern mother who kicked us out of the house after college and said, "Go build your lives." And I'm grateful to her for that. That's what I did. I moved to New York City and I got to work.

I was very lucky in my 20s. I had so many green lights. I was lucky enough to fall into a startup called HotJobs.com, which in the 90s was one of the big early-internet success stories.

I was a very early employee. I was on the leadership team. We IPO’d. We sold to Yahoo for over $400 million. I made my first batch of money. I bought a house in Lake Tahoe. I went to Stanford Business School. It was great. I wouldn't change a lot about my 20s. It was a blast.

Internalizing Failure

When I got out of Stanford, I walked into the hardest 10 years that I could have imagined, filled with humiliation, frustration, and self-doubt. I was trying to build startups, and over a 10-year span, all three startups failed.

When the first company didn't work, I was stunned. It knocked the wind out of me, and for a long time. From that point forward, I internalized failure to an irrational and almost obsessive degree. I thought that my destiny was failure and my luck had run dry. I kept thinking, "I'm not good at business." I was also dealing with a lot of really alpha people. I was in constant board meetings, raising money and running around New York City with a lot of very aggressive people. They sensed my self-doubt and ate me for lunch.

By the end of that stretch, by the time I was 39, I was battered. My self-esteem was so low, and I was suffering from terrible anxiety, fighting off panic attacks. I thought I was going to have a heart attack or end up in a sanitarium, like those lost housewives in the 1950s, wandering the gardens at some institution in upstate New York.

It got so bad that I just broke. I snapped into rational thinking. This startup that I'd been working on had gotten so bad that I realized, “This isn't my problem. I've done what I could do, and I need to just walk away from this.” I recognized the spiritual destruction I was letting happen to me. That happens in careers, and it happens in life. You’ve got to be careful because if you let that happen for too long, you give yourself over to it, and your ‘self’ is gone. 

I hit this rock bottom point of spiritual destruction where I just broke, and it brought me back to where I needed to be, which was thinking clearly and with confidence.

My clear-thinking epiphanies included these: 

1. I'm not building startups anymore. The probability of success is too low, and there are too many things I can't control because they aren't my companies. 

2. I'm not working for anybody else anymore. That's over. I'm not working for other people anymore. 

3. Hilariously but meaningfully, I'm not getting dressed up anymore. That was a big thing. No more blazers and heels and skinny jeans going to board meetings all the time. I'm not getting dressed up for anybody anymore.

These 3 deals I set with myself were an act of defiance and a form of protection of my own spirit and of my core values. I remember thinking, "I don't know what I'm going to do, but I'm not doing this. I'm going to push my raft off this dock and just shove into the unknown and see what happens."

Into the Unknown

A few things happened right away that were very helpful in my thinking. For one thing, I randomly picked up a Tony Robbins book, Awaken the Giant Within, and it changed my life. He is a genius. That got me off on a self-help journey to repair my self-esteem, and it was something I desperately needed.

And the second thing — in a very clichéd way, I re-read The 4-Hour Work Week. Thank you, Tim Ferriss. That helped me a lot. I've never had a four-hour work week, 0% chance of that ever happening, but I have accomplished lifestyle design and it was Tim’s book that made me think, in another act of protection of spirit and self: “I’m doing that.”

The third thing that happened was very random. I was standing in line at the bar at a fundraiser for my kids’ school waiting for a drink. There was one of those just sort of obnoxiously successful dads in front of me, the kind of guy who makes you feel really badly about yourself (!). He casually said, "Success has been easy for me. I've just always done what I'm good at."

That punched me in the stomach. I was like, "How have I never thought about this before? Just do what I'm really good at. Oh and what am I good at, by the way?" I had to think. What's the thing that I'm really good at that I could build on? I've always thought of myself as this utility-belt business person. I can come in, I can raise money, I can manage a board meeting, I can do a board deck, I can manage a P&L. I can manage cash flow, I can manage a product roadmap. I can manage a growth roadmap. But I'm not good at everything, and nobody is, and some of that I was outright bad at in retrospect. 

There is one thing I knew I was good at. If you lined up a hundred people in a row, I’d be the best at it. And that was marketing. Growth. Since I was a teenager doing an internship at a PR firm, I’ve always been able to sit in a chair and see what to do to grow something. Looking back at what I'd done with those startups I had to recognize and give myself credit for the successful growth strategies despite the overall companies having hit the shoals. For example I had made a social app go viral with no marketing budget — a thousand signups a day. Legitimately viral. That's hard to do.

I’m good at marketing — that was instantly clear to me. But then the question was, "What am I going to do about that?" I had read the I Ching a while back, the ancient source of wisdom behind Taoism and Confucianism. There's this beautiful concept in the I Ching about putting together a life. In life, there are two modes of being — yin and yang. They're complementary, and they together are the composite way of building your path. 

One of those modes (yang) is when you are in the arena. It's out there being in full-on action mode, sword in hand, attacking, fighting. But the other mode complementary to that is retreat (yin). And that mode is going back up to the mountain and working on yourself. It's like when Luke Skywalker goes to see Yoda to reflect, sharpen skills and gather strength. Sometimes you need to retreat and go inward before going back out into the fight, and this was a time in my life that I needed to do that.

I was 39 and I was privately very down on myself, but I was externally a very known person in the New York tech scene, which was small at the time. I always had a ton of opportunities from VCs putting me into different companies. There was no shortage of opportunities, but I didn't value that. I thought, "It's just going to be the same thing on repeat. I need to go work by myself this time, to go to the mountain." A lot of people would've just kept the paycheck and the reputation and the network going. But I didn't see any value in doing that, I felt I needed to retreat and strengthen myself because I wasn’t happy with the outcomes I was getting.

And so I deliberately retreated. My family — my husband, kids, and I — moved to the mountains of Colorado. You don't have to take the I Ching that literally and move to a mountain! It's more figurative. But for me, that's kind of the lifestyle design piece, I like snow and fires and wilderness and being outside and having some sense of mystery in where you exist, and that really is just how I wanted to live. 

Three Legs of the Stool 

During this time of retreat I reoriented myself in a way that made me successful quickly. And not just successful, but happy and fulfilled. And it worked because I really put together 3 legs of a stool and these I think are the pillars of success, and anyone can follow this same recipe.

The first leg of the stool was understanding and building on my gifts. Not wasting time on things I was only ok at or worse. "Okay, I know my gift. I am, with great humility, going to spend years getting to be the best at it." 

The second leg of the stool was in a very direct way, optimizing my mental game. “I need to fix my self-esteem. I need to fix my self-narrative.” And I spent a few years burning through self-help books, doing all the exercises, getting myself to the point where I really had an aggressive success mentality, and that was life-changing for me. I’ll talk more about these books in future posts. 

On the marketing track, there were two sub-tracks within that to help me get really freaking good at it. One was growth hacking. In the dark of the night, my dear friend Jeff Manning and I spent years just spinning up businesses with one goal and one goal only — to make money. Build an instantly profitable small business, enrich ourselves. Generate free cash flow. And we did exactly that; we spun through business idea after business idea, a couple of which were hilariously successful.

When you do little growth hacking ventures like that, you get really good at marketing because it's marketing with your bare hands. You have your bare-knuckled hands in the plumbing — and you get a powerful understanding of how to drive traffic around the internet, how to drive clicks, and what people care about. You realize that people are all the same, they have the same wants and needs. How do you write copy? How do you get people to buy stuff? How do you tap into those core wants? Those questions are the basis of marketing.

On the other side of my marketing life, I was doing white-glove consulting. I would go into an Eileen Fisher or some big private equity-backed company to give them a revenue growth roadmap. So, "You're growing at 10%, you want to grow at 30%. Okay, let me study your direct-to-consumer business and tell you what to do. Here are the three things you should do." I loved that work.

After a few years of doing growth hacking and white-glove consulting in parallel, I realized there’s a third leg in the stool. Leg one is understanding your gift. Leg two is getting your head into a successful place. Leg three is purpose and values.

The brand work gave me a strong sense of purpose. I'm very romantic about brands, almost religious about it. I believe great brands really lift us all up. Steve Jobs put it beautifully: "When you bring a great brand into existence, it ratchets up our species." A great brand gives us its personality, and we all sit up straighter. We are better at shooting our arrows at the sun because of those brands. And that gives me a sense of purpose. That gives me a sense of religion about the work.

At the end of that period, I decided to start an ad agency with my business partner Zack Peacock, a top 1% marketer who I’d been bringing into the consulting work. So we started Chief Detective. The genesis of it was really to bring these two pieces of my life together — to combine the tactical excellence and the velocity and joy of growth hacking, with the sense of purpose of building lasting brands that ratchet up our species. To put growth hacking in the service of building the next generation of great American brands. 

1. What are my gifts? 2. Get my head together. 3. Do it with purpose. When these three things all clicked together, I was at a new level of success almost instantly.

With purpose by the way, there are two sides of the coin. You move away from things that can feel like spiritual destruction, things that degrade you, whatever they may be. You have to protect yourself. You've got to protect the pilot light within yourself and move away from things that dim it. It took me too long to understand the importance of moving away from spiritual destruction. I endured things like that for way too long. So be careful. Protect your spirit. That is one side of purpose. And then the other side of purpose is what you are actively moving towards? What's your core value? What makes you feel alive? That's what you move towards and it’s the other side of the coin of purpose.

For me, it's always been: “With all thy getting, get understanding.” That's always oriented my business activities. What I am trying to get out of work is ultimately “self.” Me. Maturity and psychological resolution, peace. Use of gifts. That's where freedom comes from: developing yourself and bringing yourself into fruition. That was my deep purpose.

A Miracle Year 

Once these pieces came together for me, I was instantly successful. Robert Greene has a story in his book Mastery, which is such a killer book, about how Albert Einstein had his miracle year of turning from a low-level patent clerk into the guy who solved the greatest, most stubborn problem of physics within one year. It's a Tony Robbins thing too. Things can change so fast, and that really is true.

Looking back on this whole stretch, I realized my 30s had been this gigantic thunderstorm, but it was a storm of creation. This is true with creating anything. There's a thunderstorm of confusion, ambiguity, and sparks. You don't realize it when you're in the middle of it. But when you get out of it and look back, you realize that there was a root system growing underneath. Once the storm clears, all kinds of learning and opportunity starts to sprout up.

So those are the core takeaways from my journey. I'm really happy with where I am in my career, with who I get to work with at Chief Detective and our clients, and what I get to work on. I love my company and my partners, everybody I do it with, and my family. I love my lifestyle. Love mountain living. And I’m sharing what I learned, because I believe it will help you get somewhere wonderful, too.

Have faith, patience, and conviction in yourself. The way you're going to develop means you’ll have to hit some tough stops along the way. Make your life a little easier and keep yourself oriented with your own version of that three-legged stool. You will get somewhere great, somewhere better than you are even imagining. 

I wish you luck and joy in the journey that you're on. I’ll be sharing more lessons learned, here and on YouTube. I hope to be maximally helpful, both for your career journey and your personal life path. The two are inextricably linked. I’ll show you how.