Jordan Ellis
Jordan has coached career changers since 2016.
Big career changes go better when you experiment first. That is the single most important lesson we have learned from coaching hundreds of people through a career transition at Northstar. The clients who thrive are rarely the ones who quit on a Friday and start something brand-new on Monday. They are the ones who tested the waters first, quietly and cheaply, while they still had a paycheck. Here is how our clients test the waters, step by step, before they leap.
Why testing beats guessing
When you imagine a new career, you are really imagining a story about it. The story is usually shaped by a few movies, a friend’s social media posts or a single great day you once spent doing something similar. Stories are useful for inspiration, but they leave out the ordinary details that make up most of a working week: the paperwork, the commute, the clients, the hours, the pay.
Testing replaces the story with real information. It lets you discover what the work actually feels like at 3 p.m. on a Tuesday, not just at the exciting moments. And it does this with very little risk. If you find out the new path is not right for you, you have lost a few weekends, not your savings.
- You learn what the work is really like, day to day.
- You build skills and contacts before you need them.
- You find out whether your interest lasts beyond the first few weeks.
- You make the eventual decision with confidence instead of hope.
Talk to five people
Short coffee chats with people already doing the job tell you more than any article. This is the first experiment we suggest, and it is the one people resist the most. Reaching out to strangers feels awkward. But most professionals are surprisingly happy to spend twenty minutes talking about their work, especially if you are polite, specific and respectful of their time.
How to ask
Keep your message short. Explain that you are exploring a move into their field, mention how you found them and ask for a 20-minute conversation, in person or by video. Offer to work around their schedule. If a mutual connection can introduce you, even better.
What to ask
- What does a typical week actually look like for you?
- What surprised you most when you started?
- What do you wish more people understood about this work?
- What skills matter most, and how did you build them?
- If you were in my position, what would you do first?
Why five people? One conversation gives you one person’s opinion. Five start to show you patterns. If all five mention long hours, unpredictable income or a particular certification, that is information worth taking seriously. Afterward, send a thank-you note and keep in touch. Some of these people may become mentors, references or future colleagues.
Clarity comes from action, not from thinking harder.
Jordan
Jordan, one of our senior coaches, says this to almost every client who has spent months turning a decision over in their head. More thinking rarely produces more clarity. New information does, and new information comes from doing things.
Run a small project
A weekend course, a volunteer role or a freelance gig shows you what the work really feels like. After the conversations, the next step is to try the work itself in a small, low-stakes way. The goal is not to become an expert. It is to find out whether you enjoy the actual tasks.
- Take a short course. A community college class, a weekend workshop or an online certificate gives you a taste of the subject and the people who study it.
- Volunteer. Want to work in nonprofit management? Join a local board or help run an event. Considering teaching? Tutor at a library on Saturday mornings.
- Freelance a little. A small paid project for a friend’s business or a local organization shows you how clients, deadlines and payment work in that field.
- Shadow someone. Ask one of your five contacts if you can spend half a day observing their work.
One of our clients, an accountant in Austin, dreamed of becoming a landscape designer. Before changing anything, she took a twelve-week evening design course and volunteered to redesign the garden at her neighborhood library. She loved the course. She discovered she disliked the physical labor more than she expected. In the end, she moved into a finance role at a landscape architecture firm, which combined her skills with the world she loved. Without the experiments, she might never have found that middle path.
After each experiment, take ten minutes to write down what you noticed. Which parts of the work gave you energy? Which parts did you dread? Did you look forward to the next session, or quietly hope it would be canceled? Those honest notes are the raw material for your decision, and they are far more reliable than the excitement you felt on the first day.
Prepare the practical side
While you are experimenting, start getting the practical pieces ready too. A career change is easier when you are not under financial pressure. For money and benefits decisions, it is wise to speak with a qualified financial professional who can look at your full situation, but these general steps help most people:
- Build a cushion. Many people aim to save several months of living expenses before a transition.
- Understand your benefits. Know what happens to health insurance and retirement plans when you leave your current employer.
- Update your story. Rewrite your resume and online profile to highlight the skills that transfer to your new field.
- Talk with your household. A career change affects the people you live with. Bring them in early.
- Set a review date. Pick a date, maybe three or six months out, to decide whether to go further, adjust or stay put.
Handle the in-between gracefully
Experimenting while employed takes some care. Keep your side projects on your own time and equipment, and check your employment agreement for anything that limits outside work. Stay engaged and reliable in your current role; your reputation and references matter, and you may want them later. There is no need to announce your plans at work until you have made a real decision.
Expect the in-between period to feel uncomfortable at times. You will have evenings when the course feels like a chore and weeks when nothing seems to move. That is normal. Keep a simple log of what you are learning about the new field and about yourself, and review it every few weeks. The pattern across those notes will tell you more than any single good or bad day.
Key takeaway: Before a big career change, talk to five people in the field and run one small real-world project. Let what you learn, not what you imagine, guide the decision.
Test before you leap
A career change does not have to be one terrifying jump. It can be a series of small, deliberate steps, each one giving you more information and more confidence. Some clients test a path and realize it is not for them, which is a success, not a failure. Others test a path, love it and make the move with a clear plan and real contacts already in place.
If you are standing at the edge of a big change and want a thoughtful partner to help design your experiments, our coaches at Northstar would be glad to help. Your first session is free, and we will start with the simplest question of all: what would you like to try first?
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