Nobody starts out good at this

For anyone between 17 and 22 who started something of their own — a shop, a service, a small brand — instead of waiting for a job to teach them the rules first.

I have spent about twenty years working with people in the first few years of their working lives, including a growing number who skip the job search entirely and start something of their own. The question I hear most often, from both groups, is some version of “am I even doing this right?” It usually arrives with a lot of pressure behind it, as though there is a right answer, everyone else already found it, and you are running late.

I want to make the case for a different question. And I want to back it with something better than encouragement, because encouragement is cheap and you have probably had enough of it. If you're the one who decided to charge for something instead of waiting to be hired to do it, this applies to you at least as much as it applies to anyone with a manager.

The complaint about your generation is a genre

Business Insider published a piece at the end of August called The myth of workplace readiness. The reporter, Amanda Hoover, opens with a story about her own first internship. She was told to email a press release to a long list of reporters. She followed the formatting instructions exactly and sent it. Her supervisor came back a few minutes later to tell her she should have blind-copied the list. Nobody had ever explained what BCC meant, because that is not the sort of thing anyone explains until after you've gotten it wrong.

That is most of what “not workplace ready” describes. Not capability. A pile of unwritten rules that only get written down at the moment you break one.

It also helps to know how old this complaint is. When the Association of American Colleges and Universities first surveyed employers on this question, it found that 63% of business executives agreed that too many recent college graduates did not have the skills to be successful. That was 2006, and the graduates being described were millennials. Fifteen years later the same organization was still finding that only about six in ten employers thought recent graduates had what entry-level work required. Before millennials it was Gen X, who were supposedly apathetic, and before that the boomers, who were going to dismantle society's morals.

I am not raising this to wave the concern away. I am raising it because if you are 19 and reading a headline about how your generation cannot function at work, it is worth knowing that the headline gets rewritten roughly every fifteen years with a new name in it.

Something did change, though

Here is the part I would not want anyone to soften for me, so I won't soften it for you.

Pew Research Center's analysis of federal employment data found that 35.5% of 16-to-19-year-olds held a paying job for at least part of summer 2026. That is up slightly from last year. It is also far below where it sat for most of the last seventy-five years. More than half of teenagers worked in most summers from 1948 through 2000, and the peak was 58% in 1978.

That job was never really about the money. It was about volume. Talking to a customer who was already annoyed before you got there. Asking a manager a question you felt embarrassed asking. Standing next to somebody who had been doing it for six years and copying what they did with their hands and their voice. Most people used to accumulate a few hundred of those small encounters before anyone attached a salary to their performance.

The other half of the story sits on the employer side, and Business Insider's reporting names it: entry-level training hours have been shrinking since the early 2000s as training budgets shifted toward mid- and senior-level staff, and by 2023 a majority of workers told Pew they did not have a mentor at all.

So what has gotten scarce is not ability. It is the low-stakes chance to practice in front of somebody who will tell you when you've got it wrong.

What employers say they are looking for

The National Association of Colleges and Employers surveys hiring managers every year. Their Job Outlook 2026 Spring Update found that more than 40% of employers said new graduates' skills were very closely aligned with their hiring needs and 56% said partially aligned, with more than 20% describing new graduates as very well prepared. The four skills they rank as most important are communication, teamwork, professionalism, and critical thinking. Employers give new graduates their highest marks on teamwork.

The more useful number is in a different NACE report, and it is not flattering, so I'll state it directly. Comparing what students say about themselves against what employers say about them, the gaps are wide. On leadership, 66% of new graduates rate themselves proficient and 31% of employers agree — a 35-point gap. Professionalism runs 80% against 50%. Critical thinking and communication both sit around 25 points apart. Teamwork is the one place the two sides nearly agree.

I do not read that as evidence that you are worse than you think. I read it as evidence that whatever you are offering as proof is not landing as proof. Those are different problems with different fixes, and the second one is much easier to solve. If you are running your own thing instead of applying for someone else's job, there is no hiring manager scoring you against this list, but the underlying skills — communication, professionalism, critical thinking — are exactly what a client is quietly grading you on every time you quote a price or answer a message.

Two more sources worth knowing about, with the caveat that neither is peer-reviewed research and I would rather say so than let them carry more weight than they can hold.

America Succeeds and CompTIA built the Durable Skills Framework after running a set of skill terms through more than 80 million job postings. Durable skills accounted for seven of the ten most-requested skills in those postings, and the top five were requested close to five times as often as the top five technical skills. Leadership and communication led. That is demand data. It tells you what employers write in job ads, not whether anybody has proven you can train these things successfully.

The World Economic Forum's Future of Jobs Report 2025 surveyed over 1,000 employers and found 81% expect to keep using work experience as their main method of assessing candidates through 2030, with a degree requirement sitting third at 43%. That is an employer survey, which captures intent rather than behavior.

Tessa West, a psychology professor at NYU, put the underlying shift about as economically as it can be put when she spoke to Business Insider: “Anyone can learn the technical skills. It's the relational skills.”

You are not choosing forever

Dartmouth renamed its Center for Professional Development to the Center for Career Design last year and shifted toward helping students identify what they are drawn to rather than lock onto a single profession. The rename is cosmetic. The premise underneath it is not. The work at your age is building a direction you can revise, not committing to an identity you will have to defend.

The Durable Skills rubric is scored across four levels: Emerging, Developing, Applying, Exceeding. It was designed specifically to evaluate people who are just starting out, defined as a year or less on the job. Emerging means you are beginning to acquire the skill. It is a named level on a real scale, which is a considerably more accurate description of where you are than “behind.”

The people who wrote that framework also included a note I wish more employers read: new hires may show no meaningful improvement in certain skills until somebody gives them training and the chance to practice on the job. Some of this is genuinely not yours to fix.

It also helps to see what revision looks like in practice. Business Insider ran a piece about a 25-year-old who spent a year on the national tour of Hairspray and nine months performing on a cruise ship, then built a $10,000-a-month freelance video business on the same skills. She describes printing out a client's script and approaching it like theater. Another ran about two sisters laid off from writing and editing jobs who started a vintage business using what their mother had taught them about finding things at estate sales. I am not holding either up as a plan. I am pointing at the mechanism: neither of them picked a lane at 19 and marched. They built something with what they already had, and what they already had came from somewhere nobody would have called career preparation at the time.

Five things the research does support

What follows comes from the research literature on self-directed and self-regulated learning. I will tell you where it is strong and where it is not, because that field oversells itself and I would rather you know that going in.

Set a goal small enough that you would know if you missed it.

Theobald's meta-analysis of 32 training programs covering 4,106 university students found planning and goal setting to be the strongest single learning strategy in the set, at g = .55, well ahead of organization and rehearsal at g = .23 (Theobald, 2021). The effect depends on the goal being specific enough to fail at. “Figure out my career” is not a goal. “Talk to three people who do work I'm curious about, by October 15” is a goal, because on October 16 you will know whether you did it.

Ask for more direction than feels comfortable.

The most-cited paper in this area argues that minimally guided instruction is less effective and less efficient for novices, and that the advantage of guidance only recedes once the learner knows enough to guide themselves (Kirschner, Sweller & Clark, 2006). The experimental version I find most convincing used trade apprentices: those with little experience performed better and reported lower mental effort when given worked examples rather than an exploratory environment, and the advantage vanished once they gained experience (Kalyuga, Chandler & Sweller, 2001).

There is a related finding that runs against the usual advice. Across 144 studies and more than 79,000 students, feeling competent predicted self-determined motivation more strongly than feeling autonomous did (Bureau et al., 2021). And in a study of first-year chemistry students, instructor support for autonomy predicted performance strongly for the students who started out least able to regulate themselves, and not at all for those who started out high (Black & Deci, 2000, Science Education). Support does the most for the people with the least of it already.

Practically: ask the question you think will make you look green. Ask to see somebody's version before you make yours. Freedom gets much more enjoyable once you know what you are doing.

Judge the task, not yourself.

Grow's staged model of self-direction is widely used, and his own later defense of it conceded something important, which is that self-direction should not be treated as a general personal quality like maturity (Grow, 1991). A study of adult music students found that even where teaching style and learner stage were mismatched, students welcomed more direction when they hit technical difficulty or unfamiliar material (Leahy & Smith, 2021).

You can be entirely independent at one thing and need your hand held at another in the same week. That is a fact about the two tasks. It is not a verdict on you, and turning it into one is the single most common mistake I watch people make in their first year of work.

When you are choosing where to work, ask how much control you will have.

This is the finding that surprised me most. A meta-analysis of 58 studies on continuing education found that learners' use of self-regulated learning strategies correlated with job control at r = .28 and with organizational learning culture at r = .26, while prior knowledge came in at r = .05 and prior continuing-education experience at r = .08 (Hemmler & Ifenthaler, 2024).

Whether your workplace gives you any latitude appears to matter considerably more than what you already know. If you are choosing between a job and building something of your own, this is one real argument for the harder path: running your own thing hands you the control this research says matters most, years before most jobs would. If you do go the interview route, ask what decisions someone in this role gets to make without checking first, and how new people usually learn the job. The answers tell you more than the job description does.

Do it with somebody, and count what you did.

A meta-analysis of work-environment support found that peer, supervisor, and organizational support together accounted for about 32% of the variance in whether training got used on the job, with peer support carrying most of it (Hughes et al., 2020). Related work found these predictors matter more for open skills like communication and leadership than for closed technical skills (Blume, Ford, Baldwin & Huang, 2010). You do not need a formal mentor to start. You need one person who knows what you are attempting and will ask you about it.

Then track what you did rather than what you meant to do. In one study, university language students were given a learning app and said on questionnaires that it would help them study independently. The tracking data showed low actual use, with most activity happening during holidays rather than during term (García Botero et al., 2018). This is true of everybody, not a special weakness of yours. Keep a count of something countable: conversations had, shifts worked, applications sent, questions asked out loud in a room.

Where this research is soft

The strongest available meta-analysis of self-directed learning in health professions education found an overall effect of d = 0.34 with very high heterogeneity, I² = 87%, meaning the studies were not really measuring the same thing (Wilkes et al., 2026). That is a real effect and a modest one.

Buried in the same analysis is the result I would most want you to carry. When self-direction was delivered as a designed, supported intervention, it outperformed standard instruction at d = 0.54. When it was left unsupported, it underperformed standard instruction at d = −0.27. Same label. Opposite outcomes. That comes from a moderator analysis inside one meta-analysis rather than a direct test, so hold it loosely, but it lines up with everything else above.

One more, because it reframes what all this is for: across adult learning studies, self-directed learning correlates most strongly with curiosity at r = .40 and life satisfaction at r = .35, and most weakly with academic performance at r = .15 (Edmondson, Boyer & Artis, 2012). The people who get good at directing their own learning do not primarily end up with better grades. They end up more curious and more satisfied. At 19 that is worth more than a five-year plan.

Three things to do this month

• Write down one goal with a date on it, specific enough that you would know on that date whether you missed — a number of clients, a dollar amount, a thing you shipped.
• Send one message to somebody running a business like the one you want and ask what their first year looked like, past the highlights.
• Pick the one thing you have been avoiding because asking would mean admitting you don't know how — pricing, taxes, a hard client conversation. Ask.

You do not need to know what your business looks like in five years. You need the next round of practice, and one person who knows you are doing it.

Common questions

How do I build professional skills if I'm running my own business instead of working for someone else?

The same way anyone does: a specific goal with a date, more direction than feels comfortable at first, one person who knows what you're attempting, and a count of something real — conversations had, quotes sent, clients booked. A manager is not required for any of it. A client, a mentor, or a fellow small-business owner can play the same role.

Is it normal to feel behind when you're 17 to 22 and starting a business?

Yes, and the research on self-directed learning backs it up: designed, supported practice outperforms figuring it out alone, while unsupported self-direction underperforms standard instruction (Wilkes et al., 2026). The gap most young entrepreneurs feel is a practice gap, not a talent gap.

What should a young entrepreneur do first?

Write one goal specific enough to know if you missed it, ask one person doing similar work what their first year really looked like, and ask the question you've been avoiding because it would mean admitting you don't know something yet.

Where I'm coming from

I design and run workshops on this for a living, which means I have a commercial interest in convincing you that structured practice beats figuring it out alone. Weigh that accordingly. The five things above cost nothing and none of them require me.

References and further reading

Reporting and labor-market data

• Hoover, A. (2026). The myth of workplace readiness. Business Insider.
• Pew Research Center (2026). After a long fade, is teen summer employment in the U.S. rebounding?
• Pew Research Center (2023). How Americans view their jobs.
• National Association of Colleges and Employers. Job Outlook 2026 Spring Update and The gap in perceptions of new grads' competency proficiency.
• Association of American Colleges and Universities. How should colleges prepare students to succeed in today's global economy? (2006) and the 2021 employer report.
• America Succeeds and CompTIA. The Durable Skills Framework.
• World Economic Forum (2025). The Future of Jobs Report 2025.
• Yu, K. (2026). I started making $10,000 a month from user-generated content in 5 months. Business Insider.
• Lichtenstein, A. L. (2026). My sister and I were laid off around the same time. Business Insider.

Peer-reviewed research

• Theobald, M. (2021). Self-regulated learning training programs enhance university students' academic performance, self-regulated learning strategies, and motivation. Contemporary Educational Psychology. DOI
• Kirschner, P., Sweller, J., & Clark, R. (2006). Why minimal guidance during instruction does not work. Educational Psychologist. DOI
• Kalyuga, S., Chandler, P., & Sweller, J. (2001). Learner experience and efficiency of instructional guidance. Educational Psychology. DOI
• Bureau, J. S., et al. (2021). Pathways to student motivation: a meta-analysis of antecedents of autonomous and controlled motivations. Review of Educational Research. DOI
• Black, A. E., & Deci, E. L. (2000). The effects of instructors' autonomy support and students' autonomous motivation on learning organic chemistry. Science Education, 84(6), 740–756.
• Grow, G. (1991). Teaching learners to be self-directed. Adult Education Quarterly. DOI
• Leahy, K. S., & Smith, D. (2021). The self-directed learning of adult music students. International Journal of Music Education. DOI
• Hemmler, Y. M., & Ifenthaler, D. (2024). Self-regulated learning strategies in continuing education: a systematic review and meta-analysis. Educational Research Review. DOI
• Hughes, A., et al. (2020). The role of work environment in training sustainment: a meta-analysis. Human Factors. DOI
• Blume, B. D., Ford, J. K., Baldwin, T. T., & Huang, J. L. (2010). Transfer of training: a meta-analytic review. Journal of Management. DOI
• García Botero, G., et al. (2018). Self-directed language learning in a mobile-assisted, out-of-class context: do students walk the talk? Computer Assisted Language Learning. DOI
• Wilkes, S. L., et al. (2026). Self-directed learning in health professions education: a systematic review and meta-analysis. Perspectives on Medical Education. DOI
• Edmondson, D. R., Boyer, S. L., & Artis, A. B. (2012). Self-directed learning: a meta-analytic review of adult learning constructs. International Journal of Education Research, 7(1), 40–48. PDF