6 Tools for Moving Forward with Confidence Even If You Don’t Know What You Want

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It’s okay if you don’t know what to do with your life. I’m not sure I’ve figured out what I want to do, and I’m not sure knowing is really all that important for your contentment or mine.

Of course, we must still make decisions about how to spend our time and what to do for work. We still need some direction so we don’t end up being bank tellers by default (no offense to bank tellers meant).

How can highly creative people find their way forward, especially if being multipassionate, multipotentialite, and perhaps a tad noncommittal ensures that you struggle to go all-in on anything?

In this essay I’m going to talk about 6 concepts, or tools if you like, that have helped me find my way without always knowing my destination: the magic word, experiments, semesters, and career portfolio.

First, let’s talk about the drawbacks of keeping your options open.

Many creatives aren’t sure we want to do forever, and that lack of clarity causes us to always have one foot out the door.

Now, most of us are aware that we’ve got too many plates spinning. Our focus is spread too thin, and with it, our time.

Let’s say you’ve got 10 little projects you’re feeding time and attention into, 10 little fruit trees growing in pots. All of them might bear fruit eventually, but the shelf next to the window has room for only two or three pots. You have to rotate them out, so they all get some sun.

Any of the trees could have grown rapidly, but your insistence on keeping all of them and the necessity of rotating them meant that none of them got abundant resources. The trickle of sustenance kept all 10 alive, but that’s it. None of them produced exciting growth or a high yield.

That is what so many creatives do. Instead of lavishing attention on one or two high-potential projects, we keep ten of them on a subsistence diet of attention.

Shelf space, that is, time and attention, are limited. Thus, many-not-few as a value, as mindset, and as posture towards work stymies growth and momentum and leads to disappointing results.

I’m speaking from personal experience here.

Because I’ve been chronically overcommitted for the entirety of my adult life, I’d look at the meh outcome for one of my many projects and wonder: “What if I had thrown 100% of my time, attention, strategic thinking, creativity, hard and soft skills, relationships, and resources at something? How might this outcome have been different?”

I knew I couldn’t reasonably expect to get better results until I consolidated my focus in one or two projects or priorities.

But I was scared. That was the long and short of it.

What if I did go all in only to find out I had made some fatal miscalculation? What if I failed? What if going all-in were really self-sabotage?

So I hedged my bets, protected my downsides, and nursed my stunted plants as though more shelf space would one day magically appear.

Okay, that’s not precisely true. Some projects were a modest success.

Hyperbole is a tool of good writers, storytellers, and comedians, and I admit to using it just now. I have seen some success with various projects while maintaining too many other projects.

Why is variety still not a strategy to be embraced?

Because the only way to coax some fruit out of a half dozen trees at once is to throw more resources at them. In the case of solopreneurs, that resource means time and money. Long hours. You can work or buy your way to progress under the right conditions.

Maybe you don’t have a life though because you work all the time. Or, maybe your health suffers.

Maybe you never see your friends. And hobbies? You vaguely recall having them but you haven’t [fill in the blank] in months.

The wake-up call for me consisted of 1) welcoming tiny humans into the world and 2) burning out hard.

By hard I mean that I didn’t want to get out of bed in the morning. Was it depression? Was it fatigue? Was it a tough season?

All I know is that I couldn’t bring myself to care much about things I used to care about. As for that box of energy I could take down off the shelf in the morning, give a good shake, and rely on to power me through the day? It was inert. Unresponsive. A paperweight. I was grim, anxious, skeptical, and impatient all at once.

You can’t keep all your pet projects and ventures and have extraordinary success with one of them and work reasonable hours and love your life. You have to pick your tradeoffs.

Otherwise, you’ll end up with that gray, overcast, drizzly, and great-now-my-socks-are-soaked resignation familiar to any of you who have experienced burnout.

You have to pick, friends. Shelf space is limited.

Naturally, this brings us around full circle to the original question: “How do you pick if you aren’t sure what you want which is why you had so many fruit trees in the first place?”

Enter the magic word.

Concept #1 - The Magic Word

For creative types and multipotentialites the goal isn’t "I need to figure out what I want to do with my life." The goal is "I need to design and finish work experiments so I have something to show for my effort. No more leaving things half finished."

The happy reality is, we can go all in on certain things for a time, produce some admirable results, pivot to pursue something else, and still be able to point back at a portfolio of worthwhile accomplishments instead of a curiosity cabinet of promising but half-finished projects/ventures/ceramic frogs painted in the style of Not Sure.

Jim Dethmer, founder of The Conscious Leadership Group, talks about how we’re always 100% committed:

“Everyone is already fully committed. You can’t get more committed. Telling yourself or others to get more committed is a waste of time. The key is not more commitment, it’s clear commitment.”

Clear commitment sounds like going all in, but how do you do that when you don’t know what you want to do with your life because you want to do many things?

You must add the magic word: next.

If your experience is anything like mine, you may not lasso a satisfying answers to the far-reaching, hard-to-answer, and all-encompassing question: "What do I want to do?" You may not have a big, hairy, audacious 30-year vision for your life.

However, you don’t have to know how all the pieces fit together before you can get started. You can ask, “What do I want to do with my life next?”

That four-letter word hits the pressure release valve and enables you to move forward with confidence.

Concept #2 - Experiments

You may not be ready to go all-in on a 3- or 5-year commitment. Shoot, even 12 months may loom in your mind like an abyss.

You can commit to a venture or project if it has a clear beginning, middle, and end.

It’s the difference between saying, “I’m going to become fluent in Spanish” and “I’m going to buy, start, and finish Level 1 of StoryLearning’s Spanish program.” You can try it, get more intel, and see if you want to keep going.

If you choose to not keep going, you can still point to having finished Level 1, a commitment to yourself kept.

This experiments framing has helped me ask better questions of the ideas and opportunities that come to me:

• Every yes includes a no, so what would I be saying no to?
• What would this give me that I don’t already have?
• Am I bored or displaying an addiction to chaos?
• What question am I trying to answer with this?
• What am I hoping will happen?

I like experiments because they enable me to pursue something wholeheartedly inside of a well-defined time horizon.

Concept #3 - Semesters

Speaking of time horizons, I like pairing experiments with semesters—that is, three to four months.

Semesters work as a wayfinding tool because we can commit to almost anything for 90 days, and we can get a lot done in that amount of time, too.

The pressure of having to know whether this next thing is the thing, the elusive white stag, disappears.

Like with a college course, you only have to decide if this next thing interesting enough to pursue for three months, and if it gives you some of the credit you need to finish a degree.

In this case “credit” is better defined as what Cal Newport calls “career capital” in So Good They Can’t Ignore You. You don’t have to know exactly where you’re taking your career in order to proactively acquire skills and competencies that can only benefit you in the years ahead.

Here are some quick examples of semesters and their corresponding credits from my recent history:

• Doing Speech Club, Mike Pacchione’s group coaching program → greater skill at and comfort with public speaking
• Optimizing an Etsy shop → getting paid to see if this is a direction I want to pursue with consulting or even a lean agency
• Publishing every weekday on LinkedIn → becoming a better writer (and building an audience at the same time)
• Selling and leading through cohorts of Business Redesign, a group coaching program → trying out this business model which also forced me to better define the outcome and create the playbooks that made it possible
• Doing Launch with a Summit, Krista Miller’s group coaching program → trying out a virtual summit as a marketing vehicle for audience growth and profitable launches

Every single one of these things is something I know how to do now, and though semesters don’t culminate in a degree in this case, they do give you something even more valuable: a career portfolio.

Concept #4 - Career Portfolio

Most of us won’t have a career like a single train on a rail crossing fifty years. Shoot, the very idea of doing the same thing your entire life may sound horrifying.

That resistance to being trapped in one career path and the concurrent struggle to define what you want, or what you want to do, can cause a low-grade existential crisis, which in turn causes indecision and inertia.

You know you have all this talent and potential, and yet, if you remain fixated on finding The Thing you want to do, then you’re 99.963% likely to not finish most of what you start.

And if you abandon your experiments or drop out of “school” before you finish the semester and get the credit, then you end up with more excuses than anything.

I’ve been building toward the solution: Use the magic word to decide what you want to do next, design an experiment, commit just long enough to have something to show for your effort, and though you may not have linear career progression, you will have a career portfolio.

Here are some past detours works in my career portfolio:

• Graduating with my Master’s degree in Literature with a focus in creative writing
• Publishing my poems in literary journals
• Writing a guide about meeting creative goals (Melting Chocolate Kettles)
• Developing and eventually selling a portfolio of 30+ iOS and Android apps (Bright Newt)
• Writing and launching a mobile app marketing guide (Appiness)
• Completing a Nanowrimo challenge (writing 50,000+ words of a novel in a month)
• Cofounding a business training library of high-quality videos for freelancers (Kicktastic)
• Cofounding, raising money for, and attempting to scale a tech startup (Closeup.fm)
• Creating and teaching a travel hacking workshop
• Writing a guide on improving your credit in 30 days
• Hosting 9 retreats for entrepreneurs (SPACE Retreat)
• Speaking at TEDx, Pecha Kucha, and various conferences
• Creating and selling physical time management cards (FoFi)
• Hosting a virtual summit (Fix Your Pricing Masterclass for Freelancers)
• Co-founding a branding and marketing studio (Balernum)
• Productizing a one-on-one business coaching engagement for freelancers
• Creating and launching a business-focused course for freelancers (Freelance Cake)
• Creating various other programs, products, and smaller courses for freelancers (e.g., Morning Marketing Habit)
• Leading a private, paid community for advanced freelancers (Freelance Cake Community)
• Starting and growing a weekly email newsletter (Freelance Cake)
• Launching a podcast (Freelance Cake)
• Publishing a children’s picture book (Grabbling)
• Publishing a pricing and money mindset guide for freelancers (Free Money)

That list is incomplete, but you get the point: I finished each of these “projects” in a meaningful way, and now I can point to a career portfolio and say to myself, if no one else, “Here’s what I’ve been doing with my life.”

I may not know The Thing (aside from not being a deadbeat husband or delinquent dad), but I have done a bunch of different things. I can do a bunch of different things.

I can be proud of what I have accomplished in my life and work, even if I’m not moving up the ranks in a large company.

Tools #5 and #6 As I Close

Some of you are tired of goals. You’re worn out with accomplishments. You may be like Annie who told me: “Philosophically, after publishing that book, I stopped making grand plans in my life because I did that, and I felt very content with where I am.”

She also said, “I'm very conscious of being present with my girls, which I am. I certainly don't work anywhere as much as I used to.”

When you’re goaled out or content, do the following:

1. Optimize for days. What do you want your days to look like? "Success" is an unhelpful word because it's too vague, but we generally know what a great day looks like and feels like, and what is a satisfying life if not a long string of satisfying days? For me a satisfying day doesn't include nonstop meetings, big egos, corporate politicking, and bureaucratic red tape. Apart from bank accounts or other vanity metrics, I know I’m succeeding (or whatever) if I’m stringing together more and more satisfying days.
2. Navigate with values. Could I make more money if I were to spend more time away from my wife and kids? Undoubtedly. But to what end? I want a clear conscience. I want to look back on a life where more people knew, because they met me, just how much God loves them. And I want to be the dad who's around so much that his kids complain about it to their friends. And I want to keep my marriage. And I want to protect the basic dignity of people I meet and do business with. So keeping my core values close enables me to quickly evaluate opportunities and move forward with confidence.

When asked what I want to do, I suspect my answer will always be “many things.” Maybe that’s why I’ve never forgotten Australian filmmaker Baz Luhrmann’s spoken word song ["Everybody's Free (To Wear Sunscreen)”], which I first heard in high school.

It’s based on Chicago Tribune column by Mary Schmich, and in it, Luhrman passes on Schmich’s reassurance to college graduates:

“Don't feel guilty if you don't know what you want to do with your life; the most interesting people I know didn't know at 22 what they wanted to do with their lives; some of the most interesting 40-year-olds I know still don't.”

If you don’t know what you want to do with your life, you’re not alone. You’ll be fine. Use the magic word, experiments, semesters, your career portfolio, your idea of a satisfying day, and your values to move forward with confidence.

For us multipotentialite types, the best option is the one that leaves us with the most options.

When you’re ready, here are ways I can help you:

1. Free Money. A pricing and money mindset guide for freelance creatives. If you’re unsure about your freelance pricing, this is the book for you.
2. Morning Marketing Habit. This course will help you build an “always be marketing” practice, become less dependent on referrals, and proactively build the business you want with the clients you want. My own morning marketing habit has enabled me to consistently make  6 figures as a freelancer.
3. 1:1 Coaching. Gain clarity, confidence, and momentum in your freelance or consulting business.
4. Business Redesign (Group Coaching). Raise your effective hourly rate, delegate with confidence, and free up 40 hours a month.
5. Clarity Session. It’s hard to read the label when you’re inside the bottle. I've done well over 100 of these 1:1 sessions with founders, solopreneurs, and freelancers who wanted guidance, a second opinion, or help creating a plan.