Episode 061

Best Career Advice: Go Where It’s Messy & Challenging - Kristi McFarland

Kristi McFarland

Is your career path a straight line or a patchwork quilt? Kristi McFarland explains why she intentionally seeks out “challenging and messy” problems to solve. Alice Tang dives into how a non-traditional career path—spanning HR, Marketing, and Strategy—can lead to a million-dollar milestone and a deeply fulfilling life.

Key Takeaways:

• Challenge the Status Quo: Why the “good stuff” is hidden in complex problems.

• Sailing Toward Success: Why your journey doesn’t have to look like anyone else’s.

• Investing in Innovation: How Kristi supports women entrepreneurs and local art.

• The Friday-to-Monday Jump: Graduating and starting a new chapter under pressure.

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“ I've been the only woman in the room, the only woman at the table, the only woman in the class. And sometimes it's hard to overcome some of that natural bias that I have. I think this group of women, this audience that you have, we need to be courageous. We need to have opinions, and we need to be comfortable sharing them.”

Lori Love, Founder of Two Paws Ranch

Clips

Go where it's messy

Where the journey started

Invest in yourself

Money is potential

Investing in a woman-owned business

Go where it's messy

Your journey only needs to make sense to you

Be intentional about what you want to see grow

Transcripts

Kristi: I had a boss very early on in my career who said something along the lines of go where it’s challenging and messy. Go where there’s a problem to be solved and that’s where you’ll find the most learning. That’s where you’ll find people who are innovating, people who are challenging the status quo. That’s where the good stuff is.

Commenator: Welcome to [music] Women’s Million Dollar Conversations with Alice Tang, where we share stories from successful business women who have saved, earned, or sold over a million dollars [music] and discuss how they built their success and insights to help you achieve your goals.[music]

Commenator: Now, let’s join the conversation.

Alice: Good
Alice: morning. I’m Alice Tang, the host of Women’s Million Dollar Conversation. Today I have the pleasure sitting down with Kriti McFarland. Kristi is the chief people and marketing officer of Imperative Logistic Group and she’s also on the board of Grand Central Bakery which is very famous in Portland and the Northwest area. Welcome Kristi.

Kristi: Thank you Alice. It’s great to be here.

Alice: Tell us about your first million dollars.

Kristi: Jeez, I think the journey starts as many do. I started working when I was 15 in retail after school. And at the time, I think I made maybe 325 an hour, something like that, in the 80s. And my parents were very smart about talking about money early on and ensuring that we were always saving from that first job. always saved 10% of what I was making. And my mom, her whole career was in banking. And she went from a bank teller when I was very young to running a large region on the east coast for a major bank. And she would tell me these stories about women who had been widowed or gone through some sort of transition in their life and all of a sudden had no idea about money, had no access to their bank accounts, just were very removed from the money that was happening in their in their household. She was very adamant about teaching me about it early on and I would, you know, kind of hang out with her on Saturday mornings when she paid the bills, things like that. [laughter] I think the majority of my path has been very work, save, invest in the right things, which for me were education, and that was it until we just steadily plotted along and got to that point.

Alice: It seems to me that your mother has been
Alice: a great mentor on the path of money. Of course, I’m sure you have other family members, but specifically you mentioned your mother. I noticed two things. One, there is inflation. The minimum wage is no longer $3.25. It’s five five to six times more. So, there is inflation and real thing audience. [laughter] And the second thing is I think we all need a mentor and at that juncture for that topic of money your mentor was your mother. You mentioned about education. Tell us a little bit more about that.

Kristi: I think that was also something that was very important to both my parents. It was clear by their example that even when they had very little, starting out as a couple in their early 20s that they invested in each other’s education and that was at the expense of pretty much anything else was making sure that they were both pursuing an education and that was the major investments that I made in myself. my own undergrad education, graduate school, and something that my husband and I talked a lot about was the best and only place really to invest in is each other. And we were living in San Francisco at the time. The housing market was completely out of reach, but investing in ourselves was not. And I remember I we got very close at one point when I was in grad school because I decided to not work and focus on going to school for my graduate degree. and we were budgeting very tightly and were wondering about the next month’s rent and I graduated school on a Friday and started a new job on a Monday and went can do this.
Alice: That’s amazing. It shows one of the things we before this recording we talked about is money seems like energy to you. Wherever you put your energy, you put that money there. I love you to expand more about money and energy.

Kristi: For me, it’s not about money as an end in itself, right? Money is the potential for something. That money is the potential for something that you need, something that you want, something that you care about, something that will potentially grow or that you believe will grow. And so I think about it as sort of a a belief in something. I see your belief sign behind you. It’s putting your money, putting your attention, putting your focus on something that you believe has the potential to positively influence your life, the life of others around you, your community. That’s what money means to me. It’s the option to see more of what I care about grow.

Alice: Honoring your values in your life. If you believe in the next generation, believe in community, believe in growing yourself instead of just ending up with chunk of money. We can never take it because we come naked. We go naked. It’s not going to come with me, unfortunately. So, it’s really freeing when we can think about it this way.

Kristi: It is when you can think about where it could potentially go and what what the ripple effects of that are. That was something my dad used to talk about a lot was that all of us have a personal ripple effect. And that can be big, that can be small, that can be intentional or unintentional in leaving more of a week behind you than a positive ripple. And so I think about that a lot too. What kind of effect am I having on those around me?

Alice: Yes. I think our action really are the evidence to the people around us whether they know us or not. They see what we do and they can choose if they can leverage that energy to better themselves. It’s easy to say, you know, people teach their kid by just role modeling, but you are also role modeling to the people around you. Whether they work for you, whether they know you or they don’t know you, just saw you somewhere and you handle a situation in your own way, they learn. So, thank you for being the role model. Now I know you focus on helping the next
Alice: generation women to be successful. Now that you arrived to today’s level as you think about sending the elevator down to them what are some of the things that you are doing right now

Kristi: directly supporting and investing in women is really important. I think a lot of women who are able to don’t really know that they can or that they have options to or what the vehicles are to directly invest in companies that they care about or businesses that they care about or funds that are supporting women who are innovating. And so there’s a couple of different ways that I’m doing that. Some is through funds or collectives of women who are investing in women owned businesses or through some direct investment that sometimes goes with mentoring, sometimes doesn’t. But it’s important to me that those women entrepreneurs have a little bit more energy behind them, a little bit more fuel behind them. And it’s not about having any sort of control over what they’re doing, but really just that that faith and that support and belief that they’re on the right track and their mission is aligned to something that I care about. So those are things that are really important to me. And when invited to play on their strategy or their business, that’s super fun. I love being able to bring my background to a company at a certain growth stage and help them get through maybe that next hurdle that that might be challenging or that they haven’t been able to see around the corner yet. I can help them see what the potential is and how maybe to get there. But I believe in trusting the people who are running that business and not trying to interfere too much unless you know they want to collaborate way.

Alice:you have very clear boundaries. It’s healthy for them and healthy for you. Even when you invested your money, you don’t interview too much about what they do.

Kristi: Yeah. It’s also I love um trust based philanthropy for that same reason and investing in or being part of collectives that are really pulling their money to say we believe in these nonprofits that they have the right leadership in place that they’re making the right decisions and rather than having nonprofits go through extensive grant processes or really try to match what they’re doing to a specific set of criteria for those funds. Being able to invest from a trust based place or grant from a trust based place and say you know what you’re doing, we’re behind you rather than having those nonprofits spend so much time and energy and resource on trying to hit a very specific grant target.
Alice: So it’s all about trust. Now one of the things you mentioned that you have taken a patchwork approach allocating your personal and professional time and resources instead of one specific path and the impact that it has created. So share with us a little bit about the impact maybe an example of that patchwork approach.

Kristi: Yeah. So I think the idea of a straight career path that you start at one company and you keep growing with that company or you move from very traditional specialist to manager to director to vice president that has never really held much interest for me and I think that it’s also it’s not as as realistic in today’s work environment. I had a boss very early on in my career who said something along the lines of, “Go where it’s challenging and messy. Go where there’s a problem to be solved and that’s where you’ll find the most learning. That’s where you’ll find people who are innovating, people who are challenging the status quo.

Kristi: That’s where the good stuff is.” This I really took that to heart. And I think if you look at my career, it looks strange. I’ve been in HR. I’ve been in marketing. I’ve been in communications and led strategy. I’ve in been in general leadership roles through lots of change and growth stages of different companies. And I think the the common thread is helping a team of people find its core purpose, find its true north, and really navigate through that change and and chaos to something different to it to a stage shift. And that’s what I love. So it doesn’t look like a traditional career path. It’s very mixed. And right now, I really love the opportunity to work at a global scale with this logistics company that I’m a part of and stay very connected locally with something like Grand Central Bakery or Tender Living Empire or just being really connected to the local art community as well. Those things are important to me. I don’t think any one role is going to reflect your values necessarily, but the opportunity to put those things together, I think, allows me to see problems from multiple different angles and contribute differently than I would from one lens.

Alice: Very good advice. I had goosebumps when you go where it’s messy and challenging and find a problem that you can solve. I guess a lot of times people pause at the place where they said well it’s going to be messy it’s going to be challenging I have enough to enough maybe making enough income or enough whatever so why walk across the line to that specific situation because a lot of those fear is worrying about the what if I’m not successful what if it didn’t turn out great and your attitude is if I may describe is even if and I’m betting that there may be one or two or just a few that is not is still messy. It’s not as successful as you expect. But you have received the learning as you walk through it. There is something to learn, something to grow in you specifically echoing back education and investing in yourself is so important. We’re grateful
Alice: for the next generation women as you’re looking at them, helping them, mentoring them, and being there to support and just cheer for them. What is one piece of advice you want to give them?

Kristi: Along those lines, I would say your journey only needs to make sense to you. It doesn’t need to make sense to anyone else.

Alice: Oh my god. Oh my god.

Kristi: So if it looks strange, if the choices that you make don’t make sense to anybody else, if you pass up a role that looks like it should have been the exact right next step for you, or if you, you know, take something that looks strange, if it’s what you believe is going to serve you now, great, go for it. Doesn’t need to make sense to anybody but you.

Kristi: And if it feels off, it is. I think about it like sailing. tack towards the horizon there. You never go straight. And so at any given point, it could look like you’re really off course because you’re going this way to go this way. And that’s okay.

Alice: Very good advice. Don’t listen to the noises. Just believe in what you pick.

Kristi: Yeah. And trust the people around you, too. Make sure you’ve got people who will tell you when you’re off course. people who will be honest with you, people who want to see you succeed and will tell you when you’re not on the right course too.

Alice: Yeah, the circle of people or advisor around you that you have handpicked for that part of the journey is important. Final question, what is your money
Alice: legacy?

Kristi: I do think about it in those multiple ways of philanthropy, innovation and direct support. So everything you buy, very choice you make at the simplest evel is a reflection of what you believe in and where that energy is going to go. So I think that’s important. But then a few select areas where you really feel like this is this is a person, this is a cause, this is a business, this is a movement, whatever it is that that you really care about, put your energy there, put your dollars there and be selective about those things. So be really intentional about what you want to see grow.

Kristi: For me personally, I want to see local small businesses grow. I want to see women entrepreneurs succeed. I want to see art and music in Portland thrive. I want to see particularly just local artists develop and grow. Those are things that I really care about. And so that’s where my energy goes.

Alice: Beautiful. We are super grateful for the opportunity to interview you. What are you grateful for today?

Kristi: I am really grateful for the community here. I’m thinking about community of friends that we have developed here. I moved to Portland about 12 years ago and I really feel connected to the community here.

Alice: Thank you so much again. We are super grateful for you. Thank you for taking time for this interview, Kristi.

Meet Kristi McFarland

Kristi McFarland Headshot

Kristi McFarland brings 25 years of experience to her role as Chief People and Marketing Officer at Imperative Logistics Group.

She leads the company’s ESG strategy, talent management, marketing, and human resource functions building capabilities for future growth.

Prior to Imperative, Kristi served as Co-President, Chief Strategy Officer, and Chief People Officer at New Seasons Market, a $700M specialty grocer. She has held senior leadership roles in people strategy, brand, and communications at Peet’s Coffee and Gap Inc. Kristi is passionate about developing the next generation of leaders, serves as a board member and advisor to local businesses, and mentors women in leadership.

Kristi holds a BA in International Studies from Dickinson College, an MA in Organization and Leadership Development from the University of San Francisco, and a certificate in Business for Social Responsibility from the Haas School at U.C. Berkeley.

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