From a ranch to Wall Street: Lessons from a serendipitous career journey

LPL Financial's chief risk officer offers five principles that helped her manage her career to take advantage of unexpected opportunities

By Michelle Oroschakoff

Aug 27, 2015 @ 12:01 am EST

The family-owned Bryan-Morris Ranch in the heart of Scott Valley, Calif. Mark Peaty

I was recently asked to give a keynote speech at the Women's Luncheon at the SIFMA Compliance & Legal Society annual meeting. The charge was to talk about my career and make it relevant to the 400 women in the room. While I was used to speaking to large gatherings and have been a public speaker for much of my life, I was initially thrown for a bit of a loop when trying to prepare for this speech.

I have no problem standing in front of thousands of financial-services professionals, a tribunal or a judge, but because this speech was about me, there was no distance between the content and myself. I was speaking to a group of my peers — senior women in financial services — and my concern was that they would not have much to gain from my experiences. So I decided that instead of advice, I would share some turning points in my life and some of what I learned from them — starting with the fact that knowing these are turning points is often only apparent in the fullness of time.

While I would like to say that my career has been orchestrated from day one, starting with my first job working as a ranch hand for my father when I drove a hay truck, built fences and even went on cattle drives, the reality is not so clear-cut. My career has actually been a lightly planned, highly serendipitous journey. However, what I realized when I started to prepare for those remarks was that while I didn't have a strategic plan for my career, I did adhere to a core set of personal principles at each step — principles that I developed through time and with experience. These principles are by no means an all-encompassing list that must be followed in order to attain success. It is quite the opposite, as everyone has a different path with many choices that they must make. So no matter where you are at in your journey, here is what I have learned along the way:

• Own your power and refuse to give it away.

• Never explain — just act like it was meant to be that way and move forward.

• Don't have a rigid plan — be flexible and open to possibilities.

• You are ready — just sell yourself.

• Always take the call — and say "yes" to opportunity, especially when it means you have to leave your comfort zone.


This is a mantra I've repeated often, especially to women.

When I was president of my high school class, some of my fellow students didn't like the direction we were taking in our key duties of raising money for the senior trip, entering floats in the homecoming parade and putting on dances, and told the faculty adviser. He came to me and suggested we have a vote of no confidence and if I lost that vote, I would resign and allow the vice president to take over.

(More: CEO of 'Best Company to Work For' divulges management secrets)

I was just 14 or 15, but I told him that we were not a parliamentary system, that a vote of no confidence was not contemplated in Roberts Rules of Order (I was also on the Parliamentary Procedure team for FFA, which came in handy!), that I was the duly elected president and was going to stay the duly elected president through my term.

I don't think he was expecting that response — he just said something like "OK then," went away and never mentioned it again.


I was inspired by my mother in this regard — one of her principles was, "Never explain. Just act like it was supposed to be that way and most people will never know the difference." She applied this to everything from cooking disasters to potential public humiliation and would illustrate it by telling the story of her mother, who was out walking her Scottie dog on Michigan Avenue in Chicago in the 1930s when the elastic on her underwear gave way. She just stepped out of them, kept walking and never looked back. I have adapted this to my life, whether it's a bad answer to a question asked in a trial or my own cooking disasters.


After law school, I went to the law firm of Morrison & Foerster, where I joined the securities-litigation group — and here is where I took that that first random step. I had gone to law school with the idea of being a criminal defense or First Amendment lawyer. Then I realized that criminal defense lawyers had to spend a lot of their time with actual criminals, which was not all that appealing, and that there were not many First Amendment lawyers who made any money. So I went to a large, well-respected law firm and joined the securities-litigation group because the best lawyer I had worked for as a summer associate was the head of that group.

Unbeknownst to me, this was emerging as a hot field — a little over a year later, I got a call from a headhunter seeking to hire people for Shearman & Sterling's newly established San Francisco litigation department. Same work, more money and responsibility — what's not to like about that?

I've stayed in the securities field for my entire career, but if I hadn't decided that the most important thing was to work for the best lawyer (rather than in a particular field of the law), then I would have had an entirely different career.


While being interviewed for the position of retail chief compliance officer at Morgan Stanley, I was asked about my management experience. Following my maxim of "just sell yourself," I very earnestly explained my experience of managing my assistant and managing a part-time employee at a video store in my first job out of college. Despite that impressive level of experience, the hiring manager didn't think that my first management job should be managing the 100 employees in compliance. Despite playing up my other skills and my career ambitions, I didn't get the job. What I did get was the opportunity to know the global director of compliance, and the firm ultimately asked me to take a different role in London where I got some hands-on management experience.

That rejection was disappointing at the time, but sometimes “no” is the best answer you can get. I would probably not have been successful and certainly would not have had the great opportunity to work overseas. Seven years later, when I was ready, I got that very job.


When I said "yes" to leaving my comfort zone and ended up as the global chief risk officer of Morgan Stanley Wealth Management, I was offered an opportunity to move to a new area of financial services — one that I had never done before — and I took it. I learned a lot from that position, including the lessons to take every challenge that you can, own it from the beginning and be grateful that your team is more knowledgeable than you are.

For instance, I had a quant team of risk modelers reporting to me. When I took them out for a group lunch, a number of them turned out to have spent their vacations defending Ph.D. dissertations (I had gone skiing!). Unlike in my previous roles, where I could have done the work of my team members, in my new role every single one of my direct reports knew more than I did about their area. I realized that it was all right that our success depended on them, not me. I could learn from them, remove obstacles to success, help them build the right relationships and celebrate their achievements


As I look back, I really consider my career, to borrow a phrase, "a random walk down Wall Street." Every step in my career offered new lessons and ultimately ended up making me an attractive candidate for LPL Financial.

Back on the ranch, I had no idea that I was already beginning my journey to end up where I am today. I am forever grateful to those bosses and colleagues, starting with my father, who demanded that I execute at a high level, forgave me when I failed, said "no" when I truly wasn't ready, took a chance on me by allowing me to spread my wings and take on new challenges, and yes, even drive cattle down the road and build a few fences along the way.

Michelle Oroschakoff is the chief risk officer of LPL Financial.

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