16 Pieces of Advice From a Career in Progress

The below was written in response to an internal Sprinklr request. The assignment was to outline your career journey. The intent was to demonstrate that non-linear career paths are a) normal and b) there are specific ways to deal with it. It occurred to me after writing it that this is very individual contributor-centric and there’s lots I’ve learned as a manger not included. We’ll save that for another time. Anyway, here’s what I submitted:

I started out as an annoyingly liberal near socialist in college with a passion for European history (I’m not kidding, my major’s emblem is a red star!). Luckily a modest instinct for self preservation prompted me to seek internships in large businesses during the summers and through some shameless favor calling and nepotism I was able to secure internships at Bose and Staples in marketing and corporate strategy respectively.

Lesson 1: Hedge your bets. The revolution may not be coming.

During the summers I was doing corporate market research and during the school year I was researching how to rally the proletariat. The unifying theme? Research. Upon graduation I sought out a job in market research. I was able to talk my way into a 2 year training program at a telecommunications market research firm by doing a report on the aviation industry. Why aviation, if all the company cared about was telecommunications? Simple. Because no one at the company knew anything about airplanes, so I was automatically an expert compared to them.

Lesson 2: You don’t have to be an expert at everything. Just the right things for the context you’re in.

I spent two years at that company. Initially they had me writing reports about network infrastructure and core routing equipment, which I found terribly boring, so when enterprises started asking about this Facebook thing that had opened up to non-college kids and this thing called Twitter which had appeared at SXSW, I jumped at the chance to research social media instead.

Lesson 3: When there’s a lateral opportunity in an area that’s exciting – take it.

It was kind of grueling work writing surveys, sending out surveys, analyzing data and then writing reports, but I learned how to process huge amounts of information looking for insights and how to tell CEOs what to do with their money even though I could barely afford to buy my own lunch. It was hard for me because I wasn’t naturally statistically minded and wasn’t well trained in that area. To be honest, initially I was terrible at it. Truly bad. But it was learn or fail. So I learned.

Lesson 4: You can learn on the job if you’re willing to take some punishment along the way.

I was laid off in 2008 when the economic world collapsed. At first it was shocking to me because I saw many people I felt were less competent than me who got to keep their jobs.

Lesson 5: Competence isn’t the only requirement for security. You also need to invest in your relationships at work and be proactive in adding value to a business. That way when things go bad, you’ll be alright.

Given the economic apocalypse brewing around me I took the first decent job that arose – helping hedge fund guys do market research. I basically had to cold call business executives and get them to consult with hedge fund investors for a nominal consulting fee. It wasn’t remotely my dream job, but you do what you’ve go to do when the Dow is dropping 500 points a day.

Lesson 6: When the world is going to hell all around you and somebody offers you shelter, take it. Don’t ask too many questions.

This job was kind of hard because it wasn’t very intellectually challenging or fun. I’d literally e-mail and call hundreds of executives to get them to do something they were sort of lukewarm to do, then introduce them to ungrateful investors who complained a lot. The plus side what that I learned how to cold call relatively fearlessly. I also learned about the notion of a funnel pretty viscerally. Looking at the world in terms of a funnel would serve me well in my later marketing jobs.

Lesson 7: The funnel. You don’t actually need to be that good at something if you just do it enough times to ensure eventual success.

After about 12 months in this job, the economy was brightening a little bit (at least in Austin). I really didn’t like what I was doing, so when a start up in town started advertising for a consulting role focused on helping businesses embrace social media I knew I had to jump on it. I submitted my resume 3 days before Christmas, interviewed the day before Christmas, agreed to an offer the day after Christmas, and started two weeks later – on a national holiday incidentally. I learned after the fact that part of why they hired me was my willingness to do what it took to interview.

Lesson 8: Keep your eyes open for new opportunities and do inconvenient things to show you’re passionate about them. It also helps to be Jewish on Christian holidays.

Taking this job (at Dachis Group) was the most intense formative business experience I ever had. My first day was a national holiday. I arrived at 8am and left at 9pm. For the next 6 months I rarely left the office before midnight and rarely got in much later than 8am. I broke my hand at one point playing basketball and didn’t see a doctor because I thought it was more important to work. I still can’t do proper pushups. This was stupid. I would much rather be able to play tennis right now than know I edited two more slides in some presentation.

Lesson 9: Take care of yourself.

Over time at Dachis Group I became one of our more senior consultants delivering management consulting engagements to very large companies. It was fun helping businesses embrace social, but really difficult. I was on the road 4 days out of 5 for months and months on end. I spent weeks suited up, sitting in random business parks around the midwest teaching people how to tweet and convincing executives to give us money to do stuff in digital. It was hard. But it was also an incredible way to sharpen my business skills on someone else’s dime. I could experiment with new technology and learn as I went while still bringing back a profit to the business.

About 2.5 years into the Dachis Group journey it was clear we were going to be a software oriented company and that services were not going to drive the value of the business going forward. We were venture backed and they wanted to see software type revenue. With that realization I increased my knowledge and involvement with our software business. I learned how it worked, advised the team on what I was hearing from clients, and started to make product collateral, host webinars etc. that marketed the product.

Lesson 11: When your company changes its focus, you should too.

This was kind of hard because suddenly I was doing two jobs that were more than full time instead of just one, but that’s okay… see Lesson 8. After a while I moved formally into the software part of our business and only worked on marketing our products. This was a big change for me, I’d been advising big companies how to do social media marketing for a while, but what about all the other kinds of marketing I had to do?

I had no idea what I was doing…

… back to learning stuff on the job. I read many books, followed lots of blogs, met many of those authors of those blogs, and also just started trying stuff and asking for help as I went. See Lesson 4. It was through this experience that I learned the basics of content marketing, SEO, building websites, marketing automation etc. I wasn’t particularly good at any of them, but I could figure things out in a lot of disciplines and could get a lot done without a lot of resources.

Lesson 12: Sometimes the ability to be modestly effective with very little resource can trump being amazing at something, but requiring lots of money and tools to get the job done.

At about year 4 in the Dachis Group journey it was clear that change was afoot. The business was slimming itself down and there were lots of furrowed brows in the C-Suite and rumors flying. Many of our colleagues left the company because of the lack of certainty and stress. We had multiple layoffs. We divested companies that we had previously acquired. We closed international offices. It wasn’t really fun. I considered quitting also, but I decided to stay. First, I’d invested so much energy in this business that I wanted to see it through. Second, who knew – maybe the company that bought us would be fun/cool. Third, my general living expenses were very much under control relative to my income and I had a decent savings buffer. I could afford to ride it out.

Lesson 13: Risks are easier to take when you have the financial wherewithal to take them. If you’re going to work in a risky industry like startup technology, you should try to be conservative with your finances.

When Sprinklr bought Dachis Group it was an exciting, scary, tricky time. Sprinklr seemed awesome and growing like crazy, but it also had the feel of the early days at Dachis Group. Long hours. Lots of innovation and effort required. Plus, our CEO invented this crazy job title called “Demand Generation” and told me to go ahead and do it. I had a title I didn’t understand, in a business I barely understood, and none of the ‘street cred’ I had built up in my time at Dachis Group. Here we go again… but I tried to keep an open mind and seize the opportunity in front of me. It was clearly a tremendous chance to help build something great. If I could just hack it.

Lesson 14: Be humble and ready to earn your reputation as many times as necessary. Your old accomplishments and reputation don’t transfer. You’ll have to prove yourself again… and again… and again…

This is when I started to seek mentors. I have a few people that I know I can turn to for help when I’m just not sure what to do. Some work at Sprinklr and others are outside the business. But they are a really valuable source of perspective and knowledge when I need help.

Lesson 15: Don’t be afraid to ask for help.

In my time here, I’ve had to learn a whole new set of skills as I’ve helped to build teams and grow them. It’s probably the most difficult thing I’ve ever done professionally. As soon as I think I’ve solved a problem we outgrow the solution we put in place and have to rethink how we do things. And we honestly don’t know the solution beforehand. Even with mentorship and so much to read out there in the world, typically we have to figure it out as we go. There might be someone out there that could just show up and solve all these problems. If they’re out there, they’re probably better suited to do my job than I am, but so far it’s just all of us trying to build a great business together as best we can.

There isn’t some magical solution or team that shows up when you reach a new milestone or outgrow an old solution. It’s still just you staring at the same people who were there the last time everything went to hell. At least this time you’re a bit smarter and wiser though.

Lesson 16: The cavalry is not coming.

And that’s how I got here. Time to get back to work.

To sum up, here are Brian’s 16 Hard-Won Career Lessons, (or at least the ones that I could think of when I wrote this):

  • Lesson 1: Hedge your bets. The revolution may not be coming.
  • Lesson 2: You don’t have to be an expert at everything. Just the right things for the context you’re in.
  • Lesson 3: When there’s a lateral opportunity in an area that’s exciting – take it.
  • Lesson 4: You can learn on the job if you’re willing to take some punishment along the way.
  • Lesson 5: Competence isn’t the only requirement for security.
  • Lesson 6: When the world is going to hell all around you and somebody offers you shelter, take it.
  • Lesson 7: You don’t actually need to be that good at something if you just do it enough times to ensure eventual success.
  • Lesson 8: Keep your eyes open for new opportunities and do inconvenient things to show you’re passionate about them.
  • Lesson 9: Take care of yourself.
  • Lesson 10: If someone else will pay for you to innovate and learn – do it. You’ll keep the knowledge long after the money is spent.
  • Lesson 11: When your company changes its focus, you should too.
  • Lesson 12: Getting shit done without any money or resources is a skill.
  • Lesson 13: Risks are easier to take when you have the financial wherewithal to take them.
  • Lesson 14: Be humble and ready to earn your reputation as many times as necessary.
  • Lesson 15: Don’t be afraid to ask for help.
  • Lesson 16: The cavalry is not coming.

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