🆓 How to Have a Regret-Free Career

Ideas on how to develop a regret-free career path during the Great Resignation

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If you’re at the beginning of your career, you likely have 40 years or more of work ahead of you. Not to scare you, but most people spend about one-third of their life working — over 90,000 hours. That’s a long time to plan for — and the truth is, you can’t really plan it. The job you have in 30 years may not exist right now or have even been heard of yet. Industries and markets change, emerge, rise, and fall. A dream company can quickly become a nightmare job (ask anyone who worked at WeWork). Between bad managers, toxic work culture, and ‘passion’ buzzwords, it can be really confusing and borderline terrifying to think about navigating your career path. How do you organize that thinking? What guidelines exist for planning something so changeable and intangible?

One of the guidelines I have found most helpful in making career decisions and planning my future has been to plan for a ‘regret-free’ career. When I’m on my deathbed, what will I have been proud to accomplish? What do I hope people say about me in my eulogy? Who will I be glad I worked with? What contributions will I have made for my legacy?

When I was a student at CMC, I was energized by learning new things and challenging myself, but I had no idea how to translate that into a career. When someone asked me what I wanted to do after graduation, I had no idea what to tell them (to this day, I can’t remember how I answered this question!). I started to seize opportunities and push myself further based on this regret-free mentality. It is because of this approach that I had jobs I never could have imagined (everything from teaching snowboarding to being a banker and impact investor) and I met amazing people who impacted me along the way. These are some of the lessons I’ve learned that have helped me develop a regret-free approach to my own career path.

1. Define your values and revisit them every once in a while. Staying true to yourself is the single greatest piece of advice anyone will ever give you — but damn, it’s hard sometimes! Going back to basics with activities like this every 6 months or annually can help clarify what is important to you as you grow. When you know your values, it makes it easier to turn down the wrong jobs, ignore outside opinions, and say yes to the things that really speak to you. Knowing my values of Integrity, Joy, and Relationships has helped me seek out jobs where I can really thrive and be my best self, and not just jobs that might make the most money or have the most prestige. That knowledge has been invaluable in turning down jobs that sounded really cool but wouldn’t have been right for me. Another exercise to try is to look at how you spend your day once you’ve figured out your values. Does how you spend your time align with those values? What can you cut back that doesn’t fit your vibe, and how can you amplify the activities that make you most excited?

2. If it’s both terrifying and amazing, do it. Anxiety and excitement are two sides of the same coin — figuring out what that looks like for you will give you some intuition to guide you in more confusing moments. Over the years, I’ve developed a few tells that pop up whenever I’m really excited about something. Usually, I can’t sleep — I’m tossing and turning thinking about it. I can’t stop talking about it or working it into the conversation. I keep searching the depths of my mind for more supporting evidence until the deck is stacked heavily in favor of whatever it is. When those things start to happen, even if there is fear mixed in, I know my gut is trying to pull me in that direction. This is what happened when I was applying for my job at Working Capital Fund. I couldn’t fall asleep because my brain was so engaged with the idea and job description, so I kept reaching out to different people at the parent organization to try to connect with the team until eventually, I got an interview.

3. When in doubt, work with the best people you can. Not every job or every moment in your career is going to present itself as an exciting, once-in-lifetime opportunity that will fulfill your wildest dreams. Some of the best stuff you will ever do will be very unsexy. This is especially true early in your career — entry-level jobs can be very tough for smart, motivated, energetic people. The surest way to do good work that you’re proud of is to work with the best people you can and with people whose values seem to align with yours. Maybe that’s a manager who is really interested in your development. Maybe it’s at a company with an incredible culture. Maybe it’s working with the smartest people you can find. When choosing between two things, the stronger experiences will almost always come from the stronger team you work with — even if the tasks of the job or the brand aren’t what you’d envisioned in your dreams. At SunSaluter, I worked really closely with the founder, Eden. She was super smart, scrappy, and had a very little ego about what would make the organization a success or where good ideas came from. So, I got a lot of freedom to try different things there as well as the benefit of working with someone who pushes themselves to learn more every day. It definitely rubbed off on me and helped me realize how much I love working with smart people. The single biggest pull to finance for me was the opportunity to work with a ton of smart people, which I knew I loved doing after working with Eden.

4. Follow the rabbit holes and pull at the threads. In work, passion doesn’t always present itself as passion at the beginning. Sometimes passion grows steadily over time when you are least expecting it. So, when it doesn’t smack you in the face like love at first sight, you have to find subtler signals to follow to unearth the things that you’re most passionate about. When was the last time you lost track of time doing an activity or completing a project? What types of news articles are you reading when no one is looking? Who do you wish you had just five more minutes to ask questions of? Starting to identify what themes, subject areas, and invisible threads keep popping up and pulling at you will help you to find a pool of passion in all the places you’d never expect to. When I started at Working Capital Fund, I didn’t know much about supply chains (the core investment area for the Fund). As I started to learn more, I found myself tracking the supply chain investment market, diving into all sorts of research reports and random podcasts on supply chains, and asking more questions of the founders who I speak with every day. Now, it’s a big area of interest for me and an expertise that I’m bringing to my new investment role.

5. The money will come. No, really. It will. If you want it and you’re working hard, it will find you. Your job is to be prepared to recognize and pursue it when it does — because it may not come from following the straight and narrow path. Maybe you won’t become the Executive Director of a prominent nonprofit to get the fat paycheck, but you might start a lucrative nonprofit consulting business. If you love writing, maybe your big payday won’t come from writing a hit novel; maybe you’ll find success applying that love of writing to teaching or marketing content instead. Your career will inevitably go through phases, and the money phase can come from anywhere…so be on the lookout.

6. ABR — always be reflecting. The way you will find the signs, the threads, and the confidence to carve your own path without regrets is by sitting with yourself and taking the time to process everything as it comes. It won’t always be good, it won’t always be positive, but there is always something to learn. It is your duty to yourself to harvest your experience for learning opportunities and growth. Don’t miss out on these important building blocks by not taking the time to reflect. Some people find journaling to be helpful; for others, meditation is it. Some even do a ‘retreat’ and give themselves a beach vacation or camping weekend specifically for this purpose! Personally, I try to write down what I worked on each week (usually Friday afternoons) and make small notes about how the various tasks, assignments, and accomplishments fit into my vision and values. Then twice a year or so, I spend a day or weekend doing a big reflection on everything and see if there is anything I want to change. That reflection helps me set my frame of mind and goals for the next stretch of time.

7. Have a plan for the crappy days. You make a mistake, you have a disappointment, someone else gets the job you want — these things happen to everyone. Literally everyone. You can be sure they will happen to you at some point. When bad stuff happens, you can recover more quickly, gain valuable learning, and experience it more deeply if you have a plan. Make a playlist for when you’re disappointed. Cook your favorite meal. Go for a run. Rewatch your favorite episode of your favorite show. Do some reflecting in whatever manner you choose. I like to go for a swim and then get a drink with a sympathetic friend. I also have some playlists with very emo titles that I fall back on. Whatever it is — set up that system before you need it. That way, you’re one step ahead when those disappointments come.

8. Trust the process because you’re the one in charge. No one knows you better than you know yourself. You won’t know what the future holds, but by knowing and trusting yourself, you’ve already solved half the puzzle. You have the weapons needed to face the uncertainty of the future. In addition, no one else will have to live with the consequences of your decision-making as deeply as you will, so make sure you’re doing right by yourself. Regrets will multiply if you ignore your own intuition and self-knowledge. When I left investment banking for a small impact investing fund that no one had heard of before, I got some very skeptical responses from a few of the bankers I worked for. One of the most senior people at the firm even told me, “well, you’re young, you can afford to take a big risk like that.” I was astonished by this — the bigger risk to me was NOT taking this job! He and I had very different values, and even though he was much more experienced than me, I knew I was making the right decision for myself.

9. Give every opportunity your all. Maybe this job isn’t the one you really wanted, or you feel stuck where you are now. But you are doing yourself a disservice if you half-ass it. You won’t be gleaning all the skills and experiences you can from it, which may be helpful down the road. In one of my earliest jobs, I had a terrible manager, I was underpaid, and I was constantly bored. Instead of skating by on the minimum (which many people at this company did), I kept asking ‘what else could you use help with?’. Eventually, I managed a huge budget, directed three other employees (even though I was entry-level), and had exposure to senior leaders. These were certainly not glamourous projects, but they gave me a lot to talk about in future job interviews. As a result, I don’t regret my time at this company, even though it would have been very easy to. Every job contains opportunities — and only through giving solid effort will you uncover those opportunities. Only by leaving nothing on the table will you be freed from the regrets that come from “what if?”

As you move through your career, you will have many forks in the road. It’s easy to get lost and confused trying to decide which way to go, especially early on. For me, accounting for regret has been a helpful compass to navigate increasingly complex career choices. That said, it’s certainly not the only way to think about choosing a career path. You may find that this list is incomplete or wrong — so I invite you to develop your own, adding the lessons you’ve already learned about how to make big choices. It’s your career and not mine or anybody else’s, so how do you want to think about your career at the end of it?

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